
EMPLOYEE BENEFITS

HOW TO MAKE THE MOST OF YOUR STOCK, INSURANCE, RETIREMENT, AND EXECUTIVE BENEFITS

JOSH MUNGAVIN CFP®, CRC®

Edited by Chris Boren & Tristan Whittingham

www.Evensky.com

1-800-448-5435

Copyright © Josh Mungavin 2018

License Notes

All rights reserved. No part of this eBook may be reproduced in any form or by any means without prior written permission from the publisher except for brief quotations embodied in critical essay, article or review. These articles and/or reviews must state the correct title and contribution authors of this book by name.

Letter from the Author

Growing up, my family worked hard to get the most out of everything we had so it would go as far as possible. I put the lessons learned from a lifetime of trying to figure out how everything works (so we could get the most out of every little thing)—to use in this book. It will show you some ways you might miss out on getting the most from what your employer offers. You may run across a strategy in this book that you can tell your coworkers about so you can also make sure they get the benefit of your forethought and planning.

Most benefit packages are so complex that it can be hard to put everything together and make decisions that will benefit you most now and in the future. You work hard, and you deserve to get the most from your benefit package. It would be a shame to spend your whole career working hard only to find out that you could have increased the value you and your family got from your work by putting forth very little effort or making proper benefit elections.

This book is intended to be as easy to read as possible. You only need to read the topics that apply to your benefits to learn how to get the most for you and your family. Some sections are more complex because the topics they cover are complex. The right use for each benefit will differ for each individual, and you should always seek advice from someone familiar with these complex benefits to make sure you make the most of them without taking unnecessary risks or risks you weren't aware of (as some Enron employees know, such risks can destroy the value created from a lifetime of work). Making the proper elections will help you build up your nest egg, improve the quality of your life, and hopefully reduce taxes and life-changing risks along the way. There are too many stories of people who did not fully think through the risks they took and lost it all.

Every year during your open enrollment period, you should look at any new benefits, changes to existing benefits, and benefits of elections you previously made to make sure they are still appropriate for your current situation and goals. I hope that after reading this book, you can confidently make your benefit elections every year.

Please pass this along to friends, family members, and co-workers to make sure they know how to get the most of their benefits.

Josh Mungavin CFP®, CRC®

Principal

Evensky & Katz/Foldes Financial Wealth Management

Josh@Evensky.com

(800) 448-5435
Contents

****Retirement

401(k), 403(b), & 457 Plans

Pensions: Buying Years of Service

DROP Accounts

Stock Benefits

Employee Stock Purchase Plan

Restricted Stock Units

Stock Options

Insurance

Health Insurance Options

Health Savings Accounts

Flexible Spending Account

Dental Insurance

Vision Insurance

Life Insurance/Accidental Death and Dismemberment

Short and Long-Term Disability Insurance

Critical Illness Insurance

Highly Compensated Employees and Executive Benefits

Deferred Compensation Plans

Capital Accounts

Quality of Life

Time-off/Sabbatical Policy

Paid Time Off, Vacation, and Sick Leave

Flextime

Work from Home

Dependent Daycare Expenses

Housing

Student Loan Repayment

Financial Advisor Fee Payment

Relocation Assistance

Legal Plan

Volunteer and Gift Matching

Tuition Reimbursement or Assistance

Employee Assistance Programs

Adoption Assistance

Family Caregiver, Maternal, and Paternal Leave

Military Leave

Discounts and Special Programs

# Retirement

401(k), 403(b), & 457 Plans

Pensions: Buying Years of Service

DROP Accounts

## 401(k), 403(b), & 457 Plans

A workplace retirement plan is one of the most common profitable employee benefits employers offer. They normally come in the form of 401(k), 403(b), 457, pension, or cash balance plans. Often, an employer will match employee contributions up to a certain dollar amount or income percentage.

Optimal Use: Strategies and Analysis

a. Mega Backdoor Roth 401(k) contributions

By using the right strategies, you may be able to contribute more than you thought possible and, in turn, save more money on taxes over time. In general, employees can only contribute up to $18,500 per year to a retirement plan with an additional catch-up of up to $6,000 per year if the employee is 50 years old or older ("employee contribution limit").1 Many employees don't realize that the maximum contribution to one of these accounts is $55,000 per year plus the catch-up ("maximum contribution limit")—and that they may be able to contribute up to that amount despite the employee contribution limit and employer matching amounts adding up to less than the full maximum contribution limit.

The strategy is as follows:

The math works like this:

Normally, this would mean you could not fund your 401(k) up to the maximum contribution limit of $55,000, leaving a full $24,000 on the table ($55,000 – $31,000 = $24,000). If you have a nondeductible 401(k) and work for a company with retirement plan documents that allow it, however, you can make a $24,000 contribution to the nondeductible part of the 401(k) and then convert the contribution to the Roth portion of your 401(k). This effectively allows you to maximize the yearly contribution to your retirement account.

A very highly compensated employee can still take advantage of this strategy because employers can only base 401(k) matching off $275,000 of an employee's compensation per year no matter how highly compensated the individual is.2 A 401(k) can provide a versatile savings account by allowing penalty-free (but not tax-free) distributions of certain amounts for a down payment on a home purchase or medical expenses. Keep in mind that any additional profit-sharing plan contributions by the employer must be considered when calculating the overall yearly contribution. It is very important to check the plan documents and speak with your HR department or plan administrator to make sure you are getting the most from your retirement plan.

b. Company Stock in a 401(k): Net Unrealized Appreciation

Net Unrealized Appreciation (NUA) is the name of a little-known tax break that can help save you money on taxes from employer stock held in a 401(k) plan if you qualify. NUA rules allow you to take employer stock out of your 401(k) upon certain triggering events, only pay ordinary income taxes on the cost basis of the stock (the price you originally paid for the stock) for the withdrawal, and then have the gains taxed at capital gains tax rates. This can be particularly valuable if:

  * You have highly appreciated employer stock (stock with very low-cost basis);
  * You have an immediate need to withdraw money from your 401(k);
  * You are retiring after age 70.5 and you have to take your first required minimum distribution (RMD); or
  * You have a short RMD period, including stretch RMDs.

The rules for an NUA distribution are very strict, and you should work with your CPA to make sure you follow all the rules precisely. The rules are as follows:

  * You have to distribute the entire balance of your 401(k) and any other qualified plans you have with the employer in a single tax year (some can be withdrawn directly to a taxable account and some can be rolled into an IRA, but there can be no money left in your 401(k) account at the end of the tax year).
  * You must take the distribution of company stock from your 401(k) in actual shares—you cannot sell the shares in the 401(k) and then distribute cash.
  * You must have experienced one of the following triggering events:

  * Separation from service from the company whose plan holds the stock (this may include certain cash buyouts of the company you work for);
  * Reached age 59.5;
  * Become disabled; or
  * Death

Potential Downsides

All tax strategies can be useful, but it is generally not recommendable to let the "tax tail wag the dog." Trying to pursue this NUA strategy too aggressively can lead to you owning too much company stock and not having your portfolio appropriately diversified. You only have a few different triggering events, which means you only have a few opportunities to distribute the stock, possibly leading to overzealous distributions in the year in which they can be made. This can lead to paying taxes at a higher-than-normal tax bracket and not leaving as much money as you would normally leave in your retirement account, ultimately leading to higher taxes in the long run because all the investments held outside your retirement account are taxed every year. Your heirs do not receive a "step up in basis" on NUA shares upon your passing. You may be charged a penalty for an early retirement account withdrawal if you retire earlier than 59.5 years old, (although in some cases you can take penalty-free distributions as early as age 55). You cannot strategically convert these assets into Roth IRA assets over the years at a potentially low tax rate if they are taken as NUA; however, any amounts rolled into an IRA and not taken as an NUA distribution can still be converted to a Roth IRA. You will have to pay any applicable state taxes on the NUA withdrawal, which may apply equally to ordinary income and capital gains.

Keep in Mind

  * You will have to pay gains (for any price changes in the stock subsequent to the distribution) on any shares distributed from the retirement account and not sold immediately as either short- or long-term gains.
  * It is generally wise to keep the NUA stock in an account separate from other company stock to simplify your recordkeeping.
  * In addition, note that the NUA is not subject to the 3.8% Medicare surtax on net investment income.

Strategic Use

  * You are allowed to "cherry pick" which shares of stock to distribute in kind to the brokerage account and roll the remainder into an IRA.
  * Your heirs are allowed to take an NUA distribution when you pass away if the shares are still held in the company plan.
  * If you separate from service before the age of 59.5, have a very highly appreciated employer stock position, and you need to make a distribution from your retirement account, you would have to pay the normal 10% early withdrawal penalty. However, the penalty will be calculated off of your cost basis. This means if you purchased shares for $1,000 that are now worth $50,000, you can withdraw the $50,000 in employer stock and only pay the ordinary taxes and 10% penalty on the $1,000 cost basis. Then you would only have to pay taxes on the remaining $49,000 at your current capital gains tax rate.
  * You may be able to take an NUA distribution and then strategically sell the shares off in small amounts over the years to keep your income limited to a level that allows for 0% capital gains rates.
  * You can use the NUA distribution to satisfy your first required minimum distribution if you are over the age of 70.5 when you retire so you only have to pay ordinary income taxes on a potentially low-cost basis amount rather than the full amount of your first distribution when you would have had to distribute money from your retirement account anyway. This can significantly reduce the taxes due on your first required minimum distribution.

c. Optimizing Taxes: Backdoor Roth IRA Contributions

This unique strategy becomes available if your 401(k) plan allows you to roll over an IRA account into the 401(k) plan. Normally, single people making over $120,000 a year and married people filing taxes jointly making over $189,000 a year are limited in their ability to contribute to a Roth IRA (the income numbers are based on your Modified Adjusted Gross Income). By using the backdoor Roth IRA strategy, a highly compensated individual can contribute to a non-deductible IRA and convert it to a Roth IRA. The problem is that any Roth conversions must be done pro-rata across all IRA accounts. This means that, if you have a deductible IRA in addition to a non-deductible IRA being funded, any conversion of IRA money would be taken from both pre- and post-tax IRA accounts pro-rata. This creates a tax on the distributions from the deductible IRA where otherwise there would be none.

To avoid this additional taxation, you could potentially transfer the deductible IRA money into your 401(k) and then convert the new non-deductible IRA contributions to a Roth IRA without creating a taxable distribution.

d. 15-Year 403(b) Catch-Up Deferrals

There may be a special provision in a 403(b) plan that allows an additional catch-up separate from the over-50 catch-up. The additional catch-up, which amounts to $3,000 per year, is available to employees who have provided the same employer with 15 years of service. The amount of the allowable 15-year catch-up deferral is calculated as the lesser of:

  * $3,000; or
  * $15,000 reduced by all prior 15-year catch-up deferrals; or
  * $5,000 x years of service, reduced by all prior elective deferrals (including all past 15-year catch-up deferrals) to your 401(k)s, 403(b)s, SARSEPs, or SIMPLE IRAs sustained by your employer.

For employees who are eligible for the 15-year catch-up deferral and the over-50 catch-up, the 15-year catch-up deferral should generally be used first; the over-50 catch-up falls second in priority.

e. 457 Special Catch-Up Deferrals

Another catch-up tool available to 457 plan participants is the 457 special catch-up deferral. This allows plan participants who are three years away from attaining normal retirement age in their 457 plan to defer:

  * Twice the yearly limit on deferrals ($37,000 in 2018, which is two times the yearly maximum contribution of $18,500 in 2018) for the three years leading up to normal retirement age; or
  * The yearly limit on deferrals plus any amount allowed in prior years that you chose not to or could not contribute. Plans will keep an ongoing list of amounts you were allowed to defer in prior years, the amount you actually deferred, and any shortfall from those years. If you choose this option, they add up all your shortfall and allow you to contribute an amount equal to the shortfall over the next three years.4

For governmental 457 plans, this additional contribution cannot be paired with the over-50 catch-up, which makes it important to use the one that will provide you with the greatest benefit or largest contribution.

Special Considerations

It is important to know whether your employer matches contributions on a per-year or per-paycheck basis. Obviously, it is in the best interest of the employee to put in the full $18,500 at the beginning of the year to maximize the amount of time the money is invested. However, if the employer matches on a per-paycheck basis, the employee may find themselves getting a 5% match on their first paycheck and no further employer contributions for the year. As a result, the employee's checks have no 401(k) contributions to match for the remainder of the year. This can lead to tens or hundreds of thousands of dollars in lost matching through the years if not caught by the employee.

Mingling Contributions Among 401(k)s, 403(b)s, and 457 Plans

If you have a 401(k) and a 403(b), the maximum amount you can contribute to both accounts combined is $18,500 (2018).5 If you have a combination of a 401(k) and/or a 403(b) paired with a 457 plan, the maximum you can contribute combined is $37,000: $18,500 to the 401(k) and/or 403(b) and $18,500 to the 457. Plus, you can make any catch-up contributions allowed. The money you save into each account should be in order of employer matching with the employer plan that matches you at the highest rate first, until the match is completely maximized; then the money should flow to the account with the second-best matching and so on until you have contributed your overall maximum contribution to all plans.

Over-50 Catch-Up Contributions

For those who will reach age 50 before the year's end, the limit on the amount you may contribute to a 403(b), 401(k), or 457 account increases by $6,000. This boosts the individual contribution limit from $18,500 to $24,500.

General Breakdown of 401(k)s, 403(b)s, and 457 Plans

When it comes to comparing 401(k)s, 403(b)s, and 457 plans, there are many similarities and few differences. The similarities include:

  * $18,500 contribution limit (2018);
  * $6,000 over-50 catch-up contribution;
  * Risk of investing falls on employee;
  * Withdrawals taxed as ordinary income; and
  * Amounts deferred on a pre-tax basis.

The major differences include:

  * 403(b)s and 457s have additional catch-up deferrals, as discussed above;
  * 401(k)s are open to most employers, 403(b)s are open to tax-exempt and non-profit organizations, and 457s are open to state/local governments and some non-profit organizations; and
  * 457 plans may not be subject to early withdrawal penalties like 403(b)s and 401(k)s.

## Pensions: Buying Years of Service

Your pension may give you the option to buy additional years of service credit, which can increase your yearly pension benefit.

Optimal Use: Strategies and Analysis

Purchasing additional years of service should be looked at as an investment decision. You should estimate the rate of return on the "investment" of buying years of service. Doing so would allow you to compare it to a portfolio you're currently invested in or one you plan on being invested in during retirement. You should also look at what you can buy as a single premium immediate annuity compared to what you would spend out of pocket to buy the years of service. You can then compare the additional increase in your pension to the annuity payment (keeping in mind whether your pension has any cost-of-living adjustments) to know whether you're being offered something that competes with what is available on the open market.

To calculate an estimated return on this investment, you will need to figure out the rate of return over a given period. In other words, you'll need to determine the amount of time you expect to collect on the pension plus any cost-of-living adjustments the pension may have. A cost-of-living adjustment would only make buying years of service more profitable.

Some employers may allow you to avoid early retirement penalties by purchasing service credits. Doing this allows you to become eligible for normal retirement at an earlier date. This might make sense if you: (1) face the potential of having to go on unpaid medical leave that will be factored into your last three years of income, (thus lowering your yearly benefit); (2) have enough money to retire and no longer wish to work; or (3) are presented with another money-making opportunity that requires leaving your employer to pursue. Purchasing additional service credit is generally done to increase your retirement benefit, but doing so can also increase the benefit to your beneficiaries if you pass away during active service. This can be particularly valuable if you have a younger spouse or a critical illness. It can be thought of as a life insurance policy that pays out over time to support your family, even if you no longer qualify for a new life insurance policy due to your terminal illness.

General Considerations

Pension calculations generally rely on the following variables: years of service, retirement age, and highest salary over a specified number of years or average salary over a specified number of years. Purchasing additional service credit adds the number of years purchased to the number of years you worked for the employer for purposes of computing your monthly benefit.

Special Considerations

One thing you need to consider is that you will be buying additional income in retirement. This may affect your taxes and Medicare premiums. You must also consider the stability of the pension plan you're buying into and the possibility that the pension will change during your retirement along with the years in which you'll be collecting the pension.

You will want to consider whether you are already vested in the pension. Buying into a pension before vesting and being laid off before you vest can have serious repercussions depending on how the pension years of service purchase works with your employer. There is the possibility of buying years of service before vesting, being laid off or leaving, and not getting any benefit from the money you spent to buy years of service in a pension you will never receive benefits from. Pensions will usually not allow beneficiaries to buy additional years of service credit once the original pension owner passes away. It's imperative that you don't put all your eggs into one basket. Relying solely on the pension money can be risky because the pension could be renegotiated and the city, state, federal agency, or employer could go into bankruptcy.

An important factor to consider is whether you can purchase the service credit with pre-tax or after-tax money. If all the money from the pension benefit is to be taxed, then it would be ideal to pay for the years of service credit with something that is pre-tax, like a 403(b) or other retirement plan. As a result, the money is only taxed once rather than twice, and you can reduce your required minimum distributions from the retirement plan for future years in hopes of staying in lower tax and Medicare brackets.

General IRS Rules and Eligibility

  * Pensions typically don't allow you to buy years of service to bring yourself up to a vesting level (although some do).
  * Some pensions only allow you to buy service at retirement or after a certain number of years of employment.
  * Certain pensions allow credit to be purchased at a discount or acquired for free for periods spent in military service, on maternity leave, under a worker's compensation claim due to disability, or for out-of-state service from a similar state, federal, or private school employer.

It's worth talking to any past and current employers to figure out the best way to combine your years of service or use previous job years of service to get a discount when buying years in your pension.

You may also find value in using your paid time off (PTO) strategically during your last working years (the years your pension calculation is based on). You may be limited in the number of hours of PTO factored into your pension calculation in your last years of employment. As a result, you may be able to get more value from your pension by strategically selling your PTO days back to your employer if that is considered when your pension is calculated. You may also be able to use your PTO during times you would normally be off work, e.g., holidays or summer for teachers, in your last years of your employment to boost the average salary on which your pension is based.

## DROP Accounts

Some employers' pension plans have the option for a Deferred Retirement Option Program (DROP), which allows you to formally retire (as far as your pension is concerned) while you continue to work. Your monthly pension retirement benefits are put into a trust fund instead of being paid to you while you participate in the DROP program. The trust fund will be invested, potentially earning tax-deferred interest for you during the time you participate in the DROP program.

Optimal Use: Strategies and Analysis

It's important to begin paying attention to any DROP program options far in advance of retirement since plans can have a five-year period for which you can participate. You will have to file the appropriate applications on time to take advantage of the longest period that you can be a participant if it makes sense for you and your financial plan.

Your DROP benefits may be calculated using a participation rate (accrual rate) on your current income or on your pension benefits. For example, let's say someone earns credits in the DROP program based off a accrual rate on their years of service and their current income ($50,000 per year), the accrual rate is 2.5%, the period in the program is five years, and the person elects to participate for the full five-year period after having worked 25 years. You determine the DROP benefit by multiplying the $50,000 per-year income by the 2.5% accrual rate, which gives you a payout rate of $1,250 per years of service. In this case, we would multiply the $1,250 x 20 for the years of service to get an annual credit in the DROP pension payout of $25,000 per year x the five years of participation for a total drop credit of $125,000.
The math works like this:

Free calculators are available online that will compute your break-even period if you invest the DROP money; going into that level of depth on this calculation, and some things that should be factored in, are beyond the scope of this book. Suffice it to say that, for most people who invest the funds at a reasonable rate of return, the time to break even when not having participated in DROP is a very long time. It may also make sense to compare the yearly benefit of an immediate fixed-annuity payment bought with the lump-sum DROP money to the yearly difference in a pension payment (keeping in mind that I'm not currently a fan of annuities), but doing so gives you a good comparison point for how much your DROP money would purchase in terms of an annual benefit.

You may also choose to participate in the DROP plan if you have already maximized your lifetime benefits payable by your pension plan. This allows you to continue adding to your retirement even though you have hit the edge of what your pension will pay you. The rate at which you accrue benefits in the DROP program may also be higher than what the defined benefit part of your pension plan offers. It's worthwhile to look at the payout available to you if you were to take the DROP assets at the end of the period and put them in an immediate annuity purchased cheaply at a fixed rate. By doing so, you can see what the amount of money would buy you in a yearly retirement benefit guaranteed by the open market compared to what your employer offers for the same period of service credits. That is not to say you should buy an annuity with the money, but it is an easy, straightforward way to compare what your pension offers with what is available elsewhere with the same amount of money.

Further, it may make sense for you to use your DROP funds to purchase a term or other life insurance policy and couple that with a pension that has a payout over a single lifetime. This dual strategy may give you more money overall than if you just got a joint pension with a payout for both spouses—and given the insurance component, it also provides money on the back end for the surviving spouse. The value of this strategy varies widely from couple to couple, so it's important to do a proper evaluation and comparison. That being said, when evaluating the life insurance, you should assume that the spouse for whom the single life pension payments are being made passes away in the first year, so the surviving spouse has sufficient buffer should the worst happen. Again, I am not a huge fan of life insurance due to the way it is commonly sold, but it makes sense to at least check the math on the cost and potential value of a fixed-term life insurance policy with an insurance agent before deciding whether to participate in the DROP program using the above strategy and what type of pension payout to take.

Your pension may have a cost-of-living increase to the pension plan for the years in which you are participating in DROP, or they may stop the cost-of-living adjustment increases for your pension benefits while you are participating in the program. It is important for you to account for this in any calculations involving whether it makes sense for you to participate in the DROP program.

The DROP program will generally allow you to name a designated beneficiary and contingent beneficiary. This means that if you pass away while participating in the DROP program, your beneficiary or contingent beneficiary will receive the DROP assets. This can be particularly valuable if you have elected for any options other than joint and 100% survivor pension benefits so the surviving spouse is left with a lump sum of money. It can also benefit the contingent beneficiary to the extent that if something were to happen to both you and your spouse, usually no one would be eligible to receive pension benefits. However, in this case your contingent beneficiary could still receive the DROP benefits that accrued during your participation in the DROP program rather than receiving nothing from your pension.

DROP programs can allow either a guaranteed rate of return or allow you to invest the funds like you would with an IRA account. It's important to know what your investment options are and if they are guaranteed before opting for the DROP program. Make sure your participation in the DROP program is in line with your risk tolerance and return goals. If you retire with enough money to not take your pension payments immediately and before you reach age 70.5, you can use the assets you hold outside the DROP program and the pension to fund your current lifestyle. It may be wise to use the years before you turn 70.5 to convert, in piecemeal, the DROP program money into an IRA and then convert slowly, as dictated by pre-modeling your taxes, certain amounts of money every year from your IRA to your Roth IRA.

This conversion over time means the required minimum distributions from any DROP money will be lower in the future. You may be able to keep your lifetime taxes lower by taking small amounts out of your IRA and moving them to a Roth at a low tax bracket. Decreasing the required minimum distributions by converting money from IRA money to Roth IRA money over the course of time may also help keep your Medicare premiums at a lower rate during your retirement, which allows additional cost savings. In addition, if you retire early enough and you have converted some of your IRA money to a Roth, you can take it out tax and penalty free if you need any money from that Roth IRA (as long as the money is not attributable to growth but the money you put in the Roth IRA that has been in the Roth IRA for five years or longer). This means that you need to keep track of how much you convert from the IRA to the Roth IRA before growth. In other words, if you convert $10,000 from the IRA to the Roth IRA and it grows to $15,000 over the course five years, it is invested so you can take out $10,000 tax and penalty free; however, you will have to pay penalties on the additional $5,000 in gains that are made in the Roth (if you are not over age 59.5). This allows extra emergency cash flow in case you need it later in life but before you turn 59.5.

General Considerations

Generally, the DROP program is valid for a specified number of years; after that point, you will have to terminate your employment. The DROP assets will generally be paid out to you as an IRA rollover. Certain job benefits may also accrue based on your previous purchase of service credits in the pension. If this money is paid for with after-tax contributions, you may find different rules for receiving the money back. You may be able to roll the ordinarily earned DROP money over into an IRA, and you may have to take an immediate distribution to a taxable account for any DROP credit earned by purchasing service credits from your pension provider. These accumulations may or may not be a tax-free lump sum payout. The proportion of DROP assets you get that are attributable to any purchase of service credit with after-tax money may be treated differently upon rollout. You may find that you get paid out to a taxable account and the rest rolls over to an IRA.

Special Considerations

Typically, once you start the DROP program you are no longer eligible to purchase pension service credit.6 It's important to purchase any credits you intend on purchasing before entering the DROP program or to know whether your employer allows the purchase of service credits after having entered the DROP program.

Make sure you file the appropriate forms if there are any changes to your employment or employer and make sure you know how DROP works before making any changes since any lapse in employment with a participating employer can cause your DROP participation to be terminated. Some benefits intended for actual retirement may not be available to you while you are in the DROP program because you are currently working, including health insurance subsidies and other programs intended to help retired employees.

It is important to know your options for reemployment after participating in DROP and formally retiring from service since some employers require you to be retired for a certain period, such as six months after your DROP termination date and your retirement date, to receive all your benefits. In some cases, if you go back to work too early, the employer will void your retirement application and benefits, including all the funds accumulated during your DROP participation, which you will ultimately have to pay back. This has very serious consequences, so if you intend on going back to work after retirement, it's important to speak with your HR department and make sure you fully understand how the DROP and pension programs work in coordination with going back to work in the future.

If you do not terminate your employment at the end of the DROP program, you may find that your retirement benefits during that point of time, including DROP money that has been put aside and growing for you, are cancelled and you are put back into the regular pension program, which may or may not be beneficial. Understanding what happens if you work past the DROP election date is important because if the DROP program has not had a positive outcome for you, it may be worthwhile to run the math and consider working past the DROP program date intentionally to accrue the pension benefits if your pension works in that manner.

You can generally receive DROP account money in a direct rollover to an eligible retirement plan (e.g., an IRA and a lump-sum payment) or some combination of a direct payment to you and a rollover to an IRA. Keep in mind that if you decide to take a lump-sum payment, you will generally be taxed on the full amount given to you at an ordinary income tax rate. This can be punitive because you may have five years of pension payments taxable all in the same year that you have been working.

It is important to note that any withdrawals from the DROP program prior to age 59.5 may be subject to a 10% penalty, similar to the 10% penalty assigned to an IRA early withdrawal. There may be a way around this if the DROP program has an associated investment plan qualified as an employer-sponsored plan. Keeping the money in the investment plan may make you eligible to take distributions prior to age 59.5 from the investment plan without facing a 10% IRA early withdrawal penalty if the payments are paid to you after you separate from service with your employer during or after the year you reach age 55. You may also be able to structure payments over the course of your lifetime from the DROP program and avoid the 10% penalty. Correctly structuring your retirement and the age at which you will need these assets is very important, so you should speak with your tax advisor and financial planner before doing anything.

Some special-risk members who are qualified public safety employees may receive distributions from the plan without the 10% excise tax if they separate from service after age 50 (people in this category are generally police, firefighters, or emergency medical service workers for a state or municipality). This means, it can be important to think carefully about your age and how long it will be before you need the DROP money before deciding whether to keep the money inside an investment plan offered by the pension provider or roll the money over into an IRA where you could be subject to additional excise taxes on any withdrawals before the age of 59.5. If you have already rolled the money over into an IRA, it may be wise to speak to your HR department about whether you can roll the money back into the investment plan and take withdrawals if you end up needing withdrawals prior to age 59.5, although this may not always be possible.

General IRS Rules and Eligibility

  * You may have to wait until you are eligible to retire under the current pension plan to participate in the DROP program. Depending on the plan, you may have to choose to enroll within a certain period based on your first eligibility date, or you may be allowed to choose when you would like to enroll after your retirement date.
  * Once you enroll in the DROP, you may not be able to add years of service to your pension.
  * You are likely limited in terms of the amount of time you can participate in the DROP program, but if you select a shorter DROP period than the maximum allowed, you may be able to request an extension up to the maximum allowed by your employer.
  * Electing to participate in the DROP program is usually irrevocable. In other words, you typically cannot decide you don't want to participate in the DROP program any longer once you have started participating. In addition, you will no longer receive service credit for years of work and the pension calculation for years worked while participating in the DROP program in most cases.
  * You may need to name a separate beneficiary for the DROP account money from your pension since that person may not automatically be the same as the pension beneficiary. Looking at who the beneficiary is and ensuring that it is who you want it to be is important.

# Stock Benefits

Employee Stock Purchase Plan

Restricted Stock Units

Stock Options

## Employee Stock Purchase Plan

Optimal Use: Strategies and Analysis

Employee stock benefit plans are generally beneficial for one of two reasons or a combination of both reasons. The most common benefit of an employee stock purchase plan is that your employer allows you to buy stock at a discount, (usually somewhere in the range of 5–15%) to the fair market value. The other primary way employee stock purchase plans can add value is that some plans provide a look-back period, allowing you to use a historical closing price of the stock. This price may be either the price of the stock offering date or the purchase date, whichever is lower.

This means that, if your employer offers a 15% discount to the share price and a look-back period benefit and the price of your stock has gone up by 10% over the period, you will get a 15% discount to the price at the beginning of the period. Then you can sell it for an immediate return on your investment.

It is usually best to maximize your employer stock purchase plan to the extent that your financial plan allows. The employer will generally allow you to use up to a certain percentage of income towards your stock purchase plan, but you will always need to keep the contributions below the IRS-dictated $25,000 per year for qualified employer stock purchase programs.7 If you buy and sell the stock on the same day with the discount, you receive the percentage discount as additional compensation with little risk, even without a look-back period, so there is at least a locked-in benefit of additional income. If there is a look-back period, the stock has gone down over the period, and you buy the stock at its current price with only a discount, which again provides you the benefit of buying a stock more cheaply, you still make money if you immediately turn around and sell the stock. If there is a look-back period and the stock has gone up, you stand to gain significantly with the combination of the look-back period and the discount along with selling the stock immediately and just thinking about the gains as additional income or additional salary rather than a long-term investment in the company. In other words, it's a win–win situation as long as the shares are bought and sold on the same day regardless of whether there's a look-back period.

Special Considerations

While there may be some tax benefits to holding on to the stock you have purchased for a certain period, it's generally best to sell the shares as soon as possible to diversify your investments. The discount to the stock price you must pay versus what the stock is worth will always be taxed at ordinary income rates. Shares held for at least two years from the first day of the offering period and at least one year from the purchase date are generally taxed at the lower long-term capital gains rates. It's important to remember that while the tax benefits may seem appealing, the stock can easily decline enough to justify the diversification of the holdings over that time. Holding the stock past the first day on which you can sell it is essentially the same as buying the stock on the open market for its present value. As investments in individual companies, stocks come with unsystematic risk (i.e., risk that can't be diversified), and so much of an employee's net worth is tied up in the company based on their personal earning power through their job, incentive stock options, restricted stock options, deferred compensation, and employee stock purchase plan. It is generally best to sell employee purchase-plan stock as soon as you can because there's no benefit above and beyond what one would get from going out into the open market to buy the stock for the employee who keeps the stock. There is a significant downside to the employee if the company suffers significantly or goes out of business.

General IRS Rules and Eligibility

  * Employee stock purchase plans usually have an upfront enrollment period during which you need to decide what percentage of your paycheck you would like to have deducted and used to buy employer stock at a discount. Depending on the company, this is generally done with after-tax money, and the qualified plans are limited to $25,000 in stock purchases per year.
  * The employer will generally have you sign up for a certain period, e.g., 12 or 18 months, and give a certain number of purchase periods (i.e., two or three six-month periods) during which your money will be put into an account. At the end of the period, the money you've saved will be used to buy employee stock at the discount offered by your employer's plan.

## Restricted Stock Units

Restricted stock units (RSUs) are issued to an employee through a vesting plan and distribution schedule after achieving required performance milestones or remaining with their employer for a particular amount of time.8 RSUs are different than incentive stock options in that the employer gives you units that represent stock for free, but you can't touch the RSUs until you've met your company's vesting. The RSUs are taxed when they vest. Some companies give you the ability to take the proceeds from a RSU in kind (meaning you receive shares either before taxes so you receive more shares but pay taxes out of pocket from outside money or after taxes have been withheld by the employer) or in cash (meaning the employer gives you the net value of the shares the units represent after taxes have been withheld). In either case, you may have the option to receive the proceeds before or after taxes. The employer may withhold taxes by selling enough shares to cover your tax liability and sending the proceeds of the shares to the government.

You may see private companies, such as Facebook, offer RSUs. This allows employees of a privately held company to participate in the stock valuation of the company during its pre-IPO days without having to meet some of the requirements of public companies or companies with more than a certain number of owners. It also ensures that shareholder rights, such as voting, don't end up in the hands of people that the founders of the company don't want to have an outsized say in the happenings of the company before it goes public.

Optimal Use: Strategies and Analysis

It is generally best to sell RSUs as soon as they've vested; otherwise, it's the same thing as buying the stock on that day. Any gains that occur between vesting and the time of sale will be taxed as if the shares were purchased on the open market on the day they vested. Any time shares are held for less than 12 months, gains will be taxed at ordinary income rates. If they are held for over 12 months, the gains will be taxed at long-term gain rates. To vest in an RSU and keep the shares, you need to hold on to the shares for 12 months to get the long-term capital gains rate (only on any gains after the date they vest) potentially leaving you overexposed to your employer's stock because your livelihood and the RSU portion of your portfolio are both in a single company. Selling shares immediately upon vesting means you pay only the ordinary income taxes that would be due anyway, you don't pay any other taxes than you would otherwise have to, and you can properly diversify the money so you're not overexposed to a single company for your work income and your investments. It's generally a good idea to think of RSUs that become vested as a bonus paid out in cash.

The strategy may be different when dealing with private company RSUs than with public company RSUs because you may want to have some exposure to company stock before it goes public that you couldn't otherwise buy on the open markets. So, you may decide to keep the shares. In such a case, you may decide to instruct your employer not to sell any of the shares to cover your tax liability but instead come up with the tax money out of pocket. You will still need to pay the taxes on the RSUs immediately, so you need to have enough cash on hand to do so. In doing so, you take on a significant risk in terms of the number of shares owned, the amount of cash spent paying for the taxes on the shares, and your time spent working for the company.

General Considerations

Keep in mind that there's a difference between a restricted stock plan, in which you own the shares and your employer repurchases any vested shares upon termination, and RSUs, in which you do not own any shares until the units vest and you are given stock or the value of the stock at the time of vesting. The settlement can occur in either cash or company stock at the time of vesting for RSUs. As an owner of an RSU, you are not a shareholder in the company, you generally do not have shareholder rights, and you may be given cash rather than stock.

RSUs are generally more valuable than options because there is likely to be some value to the shares at the end of the vesting period. The shares can be sold for something, whereas incentive stock options may be at a strike price lower than the current stock price; this means it doesn't make sense to exercise the stock option at the end of vesting, leading to a complete lack of value. This means that, if you're given the choice between incentive stock options and an equivalent amount of RSUs, it's generally best to choose RSUs because there's likely to be some residual value unless the company goes completely out of business. If choosing between the two, you want to see a large amount of incentive stock options in comparison to the RSUs to make the incentive stock options a justifiable bet not only because you need to buy the stock option (so you only get the difference between the price you can exercise the stock option at and the current price) but also due to the volatility of the nature of the option itself. Keep in mind that if you can fill out a beneficiary form, it's always worthwhile to do so just in case something happens before you have handled your vested RSUs.

Special Considerations

Because the stocks can't be touched until you vest, it's important to know your vesting schedule and what shares are on the line if you plan on changing jobs. That way, you don't quit a job right before a large vesting period. In addition, you can bring up how many shares you're leaving on the table and what level of compensation that relates to when negotiating a new job to give you a better angle for negotiating the salary that is comparable to your previous employer's compensation package. It may be possible to negotiate a one-time upfront restricted stock offer from a new employer with a vesting schedule similar to or possibly longer than your existing employer's RSUs but with a similar value so you are no worse off for leaving your current employer and joining a new employer.

If you receive restricted stock rather than RSUs, you can make what's known as an 83(b) election with the IRS. The election tells the IRS to lock down the fair market value at the time the stock is granted so you owe income tax on the grant date between the fair market value of the grant and the amount paid for the grant. The election starts the clock earlier for capital gains purposes, so when you eventually sell your stock, the second round of taxes is paid on any gains in the stock price after the election but before the vest. This introduces a new, potentially huge risk. You have paid taxes on the pre-vested shares, which were granted, that you can't get back if you leave the company, pass away, or get fired before they vest. If the stock declines in value after the taxes are paid at ordinary income tax rates, you can deduct the losses, but that may mean you have paid taxes at a higher rate than you can deduct the losses at.

General IRS Rules and Eligibility

Vesting can generally be either time or performance driven; for example, you may find a yearly vest of 25% of your grant for four years, once the company hits a predefined goal, or once you as an individual hit a preset goal. This can also be tied to the IPO of the company, which means the company can specify a period after the IPO during which employees cannot sell shares so the market is not flooded with shares of the stock. Some companies allow you to defer the settlement of RSUs for income tax purposes so you can choose to vest the RSUs in years with low earnings to be in a lower tax bracket when your shares vest. A change in timing on the vesting of your stock requires two conditions to be met:

  * The initial deferral election is made prior to the year in which the compensation is earned; and
  * Payments are made according to a fixed schedule or tied to an event, such as end of employment, disability, or death.

## Stock Options

Incentive stock options and non-qualified stock options are relatively complex instruments that led me to debate whether to include them in this book. I believe this topic requires professional modeling and opinions along with a comprehensive knowledge of all the workings of an individual's finances. I fear that as simple as I have tried to make this book read and as overly simplified as I have made the topic, I run the highest risk of giving the reader enough information to be dangerous but not enough to make a truly educated decision in this section; however, I would be remiss in excluding it. At the same time, I am concerned that not enough information can be given about stock options in such a brief book when the topic of stock option analysis could comprise an entire book and still be inconclusive. Bill Gates said,

When you win [with options], you win the lottery. And when you don't win, you still want it. The fact is that the variation in the value of an option is just too great. I can imagine an employee going home at night and considering two wildly different possibilities with his compensation program. Either he can buy six summer homes or no summer homes. Either he can send his kids to college 50 times, or no times. The variation is huge; much greater than most employees have an appetite for. And so as soon as they saw that options could go both ways, we proposed an economic equivalent. So, what we do now is give shares, not options.

With this in mind, I will try to provide the easiest, most simplistic routes in which to judge incentive stock options with the caveat that you should not make decisions concerning these instruments without consulting a professional. This is all to say that including any of this information gives the reader a sense that they have enough information to decide, when in fact I believe the only reason to include this information is so the book doesn't feel incomplete. Stock options are very complex and volatile, but they have a lot of value if used correctly with discretion and the best luck. While the upside is substantial, the downside is likewise substantial, and both should be considered when making any decisions concerning stock options.

Fundamentals

Before we begin discussing stock option strategies and analysis, a grounding in some fundamentals on the topic is in order.

A stock option is the right to buy a specific number of shares at a preset price (i.e., the exercise or strike price) during a certain period. There is generally more upside potential in stock options than in restricted stock because of the inherent investment leverage in options contracts.

The strike price is what it costs you to exercise an option (i.e., to buy a share). It is commonly called an exercise price since you're exercising the option to buy the share at a specified price.

The value of your options (i.e., the options value) is the market price minus the strike/exercise price along with an adjustment for time value that decreases as you get closer to the end of the option time period.

The option is in-the-money **** when the value of the option is greater than zero (i.e., when the strike price is less than its per share value). The option is out-of-the-money when its intrinsic value is zero (i.e., the price you can buy each share for with your option is higher than its current cost on the open market).

The time value is the premium paid over the current exercise value of an option because of the possibility that the option will increase in value before its expiration date. The time value of an option naturally decays as you get closer to the expiration date, reaching zero on the expiration date, but the option will almost always be worth more than its current exercise value prior to the expiration date.

Optimal Use: Strategies and Analysis

While a host of insights and variables should be considered, this section includes some of the most common ones and provides a framework you can use to conduct a preliminary analysis and determine how to begin pursuing a stock option strategy.

It is always very important to know when your options will vest so you can exercise and/or sell the options because missing that date can be very costly. The expiration date on the stock options are critically important because the time value of the option decreases as you get closer to the expiration date and the value of the options more closely approaches the value of the stock. Keeping this in mind, any time you exercise employee stock options before their expiration, you lose the remaining time value.

Any change in the market price of your stock can have a very large impact on your option value. Any time you have leverage on investments, not only your gains but also your losses are potentially magnified. So, while options have more potential upside than RSUs, they also have more downside, and they may expire worthless since the price you can buy the shares at may be higher than the market price. In addition, if you exercise your options and the price decreases, the money you spent to purchase the shares and the taxes you had to pay are already money out of pocket that you may not ever get back.

It almost never makes sense to allow an in-the-money stock option to expire without exercising it. As mentioned above, a stock option is considered in-the-money when the stock is trading above the original strike price (i.e., you can buy the stock through your option cheaper than you can buy it on the open market). It makes much more sense to exercise the in-the-money stock option and immediately sell the stocks acquired (in turn realizing the short-term gains) than it does to allow that money to slip through your hands by letting the options expire.

Keep in mind that while it's easy to think of incentive stock options as stock, they are not stock since there is inherent upside and downside leverage in your incentive stock options; and so an analysis of the stock options and their value is essential before making any decisions. The analysis should include the in-the-money value, the cash-out value, and a Black-Scholes value at the very minimum. There are many other ways of looking at stock options, but these are the bare-bones minimum when looking at any stock options and determining which options would be primary candidates for exercise and diversification.

  * The in-the-money value calculation is the difference between the current fair market value per share (i.e., the current stock price) and your exercise price multiplied by the number of options you have. This only applies to the number of shares you have vested; it does not count the number of unvested shares you have options in. You can calculate the cash-out value by subtracting the amount of taxes you would have to pay on your vested grants from the value of your vested grants so you get an after-tax value equal to your cash-out value on the grants.
  * The Black-Scholes method of evaluating the value of an option should be a section unto itself in this book. It allows a deconstruction of the in-the-money value and the time value. You must know the expiration date (i.e., the time until the option expires), the strike price (i.e., the price you can buy the stock at), an estimate for the volatility of the stock, and the risk-free rate of return. Note that an option with a high volatility is an option where the stock fluctuates substantially; it will have a greater time value than an option for a stock that does not fluctuate substantially or that has low volatility because the volatility of the stock reflects both the potential upside and downside of the stock. The option value is enhanced by the theoretical ability to earn above the risk-free rate of return without investing anything (i.e., the higher the risk-free rate of return, the higher the time value of the option). Almost the entire value of the Black-Scholes model lies in finding the time value of the option. The time value is important in determining when to exercise options because as the time value decreases the value of holding the options also drops. In-the-money options with low time values are generally good candidates to diversify. The Black-Scholes value is equal to the in-the-money value plus the time value. The time value of vested options is important because it measures the company-specific risk or general market-specific risk associated with continuing to hold the options.
  * The cash-out value is the amount of money you would receive by selling your stock options at their current value. This allows you to see how much money is put at risk by not exercising your currently vested stock options.

Once you compute the above values, it's helpful to look at them in aggregate to see how leverage plays out in your stock options. This modeling does not give you a clear decision as to which stock options to exercise or provide a judgement with regard to exercising, but it at least lets you see the breakdown of where the value is coming from, how much is at risk due to time-value decay if the stock should remain flat, whether the market value of the options illustrates more or less volatility in the stock than you anticipate, and what the consequences of the stock going down might be so you can make a better informed decision.

General Considerations

There are two general ways to exercise stock options: pay cash or net shares. With the pay-cash exercise, you pay for the entire value of the stock options to be exercised out of pocket. With the net shares approach, some of the shares you can buy are sold immediately to pay the taxes on the exercise for the remainder of the options. You own less shares after the exercise, but your tax has been paid based on the benefit of having the stock options.

Any time you elect to have all stock options purchased rather than a certain number exercised and sold and then the remainder purchased, you do have to pay out of pocket to buy the number of stocks you are allowed to buy at the specified rate.

It's important not to delay exercising your stock options until the last-minute, waiting for your stock price to go up. If you miss the deadline, your options will expire worthless. These options are not stock; they are options to buy stock, and if you let the option lapse, you no longer have the benefit of buying the stock at your option at a cheaper cost than the list price. In addition, remember that if you retire, leave your company for a new job, or are laid off or fired, you may have no more than 90 days to exercise any stock options; therefore, it's incredibly important to clarify what you can do with your stock options and what you need to do with your stock options before you leave a company or as soon as possible after you are let go.

As illustrated in the above chart, it's also important to understand that incentive stock options have a leveraged nature. This means your incentive stock options are inherently more volatile or risky than the value of your employer stock, which can be a significant factor when you want to potentially decrease a single company-specific risk. The chart below shows that as the value of the stock increases, the value of the options dramatically increases; however, the value of the options is near zero below a certain point.

Special Considerations

Incentive stock options are usually granted to employees, and they are not taxed at the grant date or the exercise date but only when the shares are sold. To qualify for favorable tax treatment, you must hold the shares two years from the grant date and one year from the exercise date. That means, if you exercise after one year from the grant date, you need to hold the shares for an additional year to qualify for long-term capital gains rates; otherwise, you are taxed at ordinary income tax rates. This can lead to people "letting the tax tail wag the dog."

For some, this is a worthwhile gamble, but it would have devastating life consequences for others. It is important to know which position you are in and not take risks that would devastate your lifestyle for the hope of a little extra gain that may not have much of a meaningful effect on the rest of your life. Even though incentive stock options are generally not taxed when you exercise the option, the value of the discount your employer provides and the embedded gain may be subject to the Alternative Minimum Tax in any given year. So, it's important to talk to your accountant to know the potential tax ramifications for exercising any incentive stock option.

General IRS Rules and Eligibility

If your company is acquired or if it merges, your vesting could be accelerated; this means, in some cases you might have the opportunity to immediately exercise your options, so it's important for you to know your exercise options. It's also important to check the terms of the merger or acquisition before acting so you know if the options you currently own in your company stock will be converted to options to acquire shares of the new company.

Unlike RSUs, stock options are not taxed until they are exercised, and if you exercise your option before the value of the options has increased and file an 83(b) election, you will not owe any taxes until the stocks are sold. If you exercise your options after the value increases but before they are liquid, then it is possible for you to owe an alternative minimum tax. So, it's crucial to consult a tax advisor before making that decision. Usually, you can't sell or exercise your stock options before vesting unless your stock option plan allows early exercise. If you can exercise your options before vesting, you can make an 83(b) election. The 83(b) election starts the clock early for capital gains by notifying the IRS to lock down the fair market value at the time of exercise rather than vesting. You have 30 days from the early exercise date to file an 83(b) election.

Non-Qualified Stock Options

Non-qualified stock options require that taxes be paid upon exercise, whereas qualified incentive stock options are generally not taxed until the stock is sold. However, there may be an alternative minimum tax at the time of exercise, so it's important to speak to your CPA to fully understand the tax implications. All options are taxed at the difference between the fair market value at sale and the fair market value of the purchase. Non-qualified stock options are taxed at ordinary income tax rates, which are substantially higher than the capital gains tax rates on which incentive stock options can be charged tax depending on the holding period of the stock purchased and sold.

Non-qualified stock options can be granted to employees and non-employees, and there are no restrictions on what the strike price can be; however, any strike price less than the current fair market value of the stock would be considered ordinary compensation and not capital gains. For example:

# Insurance

Health Insurance Options

Health Savings Account

Flexible Spending Account

Dental Insurance

Vision Insurance

Life Insurance/Accidental Death and Dismemberment

Short and Long-Term Disability Insurance

Critical Illness Insurance

## Health Insurance Options

Health insurance options change every year, so it's important to look over new healthcare options every year. Think about how these options are presented to you, think of everything that will affect you and your family, and reanalyze the math you did the year before to make sure the plan you're in, if still available, is the right plan rather than just staying in a plan that may no longer be right for you. You have to look beyond the premium. While a low-cost plan might be nice if you don't expect anything to happen, remember that everyone is healthy until they're not.

Optimal Use: Strategies and Analysis

You must look at copays (i.e., the fixed amount you pay for services), deductibles (i.e., the amount you pay before your insurance starts paying), coinsurance (i.e., the percentage of costs covered after you meet the deductible), and out-of-pocket maximums (i.e., the most you'll have to pay before the insurance pays 100% of any remaining costs). Depending on your health that year, going with a lower premium might end up meaning you need to pay higher out-of-pocket expenses. Things to think about include new babies, newly diagnosed illnesses, or a recent marriage. You also want to know if you have dental and vision coverage and how long it has been since you've used either. It's also important to look over which health plan will be most beneficial to you over the year and not let the "tax tail wag the dog" by looking at the tax and savings benefits of a Health Savings Account (HSA) and whether a plan without a high deductible will be more beneficial for you over the course of the year since taxes aren't everything (HSAs are discussed in more detail in the next section).

Generally, plans cover preventative care such as annual physicals, gynecologist visits, mammograms, and immunizations at no cost, but that varies from plan to plan. Make sure that you can use the doctors you want to go to under the plan you choose and that you're not limited to a doctor who works for an insurance company you may or may not be happy with when you already have an existing physician.

One way to compare a traditional healthcare plan and a high-deductible plan is as follows: take the annual premium, deductible, coinsurance after the deductible, out-of-pocket limit, any employer contributions to the HSA, and the tax break you get from the HSA to do a little math. The math works as follows: look at the cost of coverage if you need absolutely nothing over the course of the year. To do that for the traditional plan, use the annual premium as the total cost. To do that for the high-deductible plan, use the annual premium minus the tax benefit of fully maximizing the HSA plan if you plan to fully do so or the tax benefit of any amount contributed to the HSA plan.

So, if the annual premium for the traditional plan is $1,000 a month, its yearly cost to you is $12,000 if you don't need any medical care at all.

In this case, if the high-deductible plan costs $500 per month, the yearly cost is $6,000 minus the tax benefit of the HSA deduction.

If you maximize the HSA as a family with the full $6,900 per year allowed and you are in the 20% tax bracket you get a tax benefit of $1,380 (Note that your personal tax rate makes a big difference, so one person's decision may be completely different than another's given the same circumstances and the same plan but different tax rates). From there, take the yearly cost of a high-deductible plan coverage of $6,000 and subtract the tax benefit of $1,380 for a total yearly cost of $4,620.

If you do not need any medical care, subtract any employer HSA contributions for the year from your effective yearly number (for this example, we'll use no money from the employer so the calculation is easy). The high-deductible plan coupled with the HSA also allows the benefit of tax-free growth on the investment of $6,900, which is a benefit you would see above and beyond the effective yearly premiums, being $7,380 less expensive (calculated as $12,000 traditional plan annual cost – $4,620 HDHP annual cost after adjusting for the HSA tax benefit, all as illustrated above).

Next, we'll look at how much the plans would cost if you maxed out your coverage for the year. In this case, let's say the traditional plan has an out-of-pocket maximum of $3,000 and the high-deductible plan has an out-of-pocket maximum of $10,000.

For the traditional plan, add the $3,000 out-of-pocket maximum to the $12,000 yearly cost of premiums for a total insurance cost of $15,000 as a worst-case scenario.

For the high-deductible plan, add the $4,620 "effective" premium to the $10,000 out-of-pocket maximum for a worst-case scenario of $14,620.

In this case, taking the high-deductible plan would be something of a no-brainer. The math changes substantially if the cost for the yearly premium under the traditional plan is only $7,000. In this case, the worst-case scenario would be the $7,000 yearly premium plus the $3,000 maximum out-of-pocket for a total worst-case scenario of $10,000.

You would then compare the traditional plan's worst-case scenario of $10,000 to the high-deductible plan's worst-case scenario of $14,620 to see a difference of $4,620 dollars in a worst-case scenario per year.

Now look at the difference between the $7,000 traditional yearly premium and the $4,620 effective high-deductible yearly premium, and you'll come up with a difference of $2,380 per year of an effective premium difference.

Now you will calculate the number of years it will take you to break even by dividing the $4,620 difference in a worst-case scenario by the $2,380 per-year effective premium difference to come up with 1.9 years to break even.

This means that as long as you don't max out your insurance every other year, you are better off with a high-deductible healthcare plan even though you will max out the high-deductible healthcare plan in some years, making you worse off for that year. In this case, you will have saved money over the long run by going with the high-deductible healthcare plan as long as you can afford to pay for your medical costs in the years with high expenses. If you find that the break-even point is three, four, or five years, it may be worthwhile to look more closely at the traditional plan. If you expect to have regular healthcare treatment needs or plan to have some level of expenses every year, you may need to alter this calculation so the 1.9 years to break even becomes a little bit longer since you will have to pay everything out of pocket using the high-deductible healthcare plan, whereas you may have some help paying in the years with a moderate amount of healthcare costs with a traditional healthcare plan.

Generally, a high-deductible healthcare plan with an HSA will be more attractive to younger people in good health who aren't expecting to have any children or major medical issues. The good news here is that if you make the wrong decision, it's only the wrong decision for one year and you're not locked in forever since you can move to the other plan at the end of the year. Furthermore, if you have any money in an HSA, you can keep that and use the HSA money whether you decide to use the high-deductible healthcare plan or a traditional healthcare plan the next year.

It's important when working through a health insurance analysis to look over the health insurance options available through your spouse or domestic partner's employer (if the employer covers domestic partners) to make sure you choose the best plans since you may want to split coverage or have both of you covered under one of the plans.

General Considerations

Will you have access to a flexible spending account (FSA) or an HSA? Both options allow you to set aside pre-tax dollars to cover future medical expenses, but there are differences between the two.

If you have the option of setting up an FSA with your insurance company, do so. Doing this allows you to use the money in the account for copays; however, remember that those funds are use-it-or-lose-it, so make sure you have a back-up plan for how to spend the money by the end of the year, such as new glasses or dental work.

Keep in mind that while HSA savings amounts are federally tax deductible, they may not be deductible for state tax purposes depending on what state you live in.

## Health Savings Accounts

According to a 2018 study, the average couple who is 65 years old today will require an estimated $280,000 in today's dollars for medical expenses in retirement, excluding long-term care.9 It is likely that the amount needed for those who are younger will be even higher. This is one reason, but not the only one, to fully fund an HSA every year in which you are eligible. In fact, I think an HSA is one of the most powerful savings tools currently available, especially if it is used optimally.

Specifically, an HSA is a tax-advantaged account created for individuals covered under high-deductible health plans (HDHP) to save for medical expenses those plans do not cover.10

Optimal Use of an HSA

In 2017, only 18% of the money that went into HSA accounts stayed invested until the end of the year. This means most people use HSA money to pay off current bills. Putting only enough money in an HSA to cover your current year's medical bills is a straightforward way to get a tax break for your non-deductible medical bills for the year, but I think there's a better way.11

A large portion of the long-term benefits of an HSA comes from the tax-free growth of the account through the years. This means that the longer you invest in the HSA, the higher your likely lifetime benefit. To get the most value from the HSA investment vehicle, fund the HSA with the most you can every year but hold off on using the funds (absent an emergency) until late in life. Retirement healthcare expenses should be one of the first uses of HSA funds. In addition to regular out-of-pocket medical expenses, you can generally use HSA funds to pay for premiums for long-term care (with the qualifying amount based on age), health insurance continuation coverage (i.e., COBRA), health insurance while receiving unemployment, and Medicare if you're over age 65 (not including Medigap).

Receipts for medical expenses that were not deducted through the years should be saved along the way. There is currently no deadline for self-reimbursements, so if you have paid out of pocket, have not deducted the expense on your taxes, and have the records, you can theoretically reimburse yourself for years' worth of expenses if you need extra money and do not have anywhere else to withdraw from or if you have more money in your HSA than you will need for lifetime health expenses.

Furthermore, if you find yourself with sufficient funds to fully reimburse yourself for all past medical expenses and cover all future medical costs, you can consider taking distributions from the HSA for living expenses. While HSAs do not have any minimum distributions after age 70.5 like IRAs, you do have the option to use the funds for anything, paying only taxes with penalties after age 65.

If the HSA account is severely overfunded and there is charitable intent, this may be the first account to turn to for charitable bequests by naming the charity of your choice as the beneficiary of your HSA. Otherwise, you may think about intentionally beginning to draw the account down slowly so taxes are spread out over the course of years. Unlike retirement accounts, HSA accounts are liquidated upon the death of the account owner, and all taxes are due as ordinary income in the year of death. Meaning, a highly funded HSA could push you into a much higher tax bracket than normal.

Finally, remember that we are always subject to changes in tax law when you are planning a very long-term tax and investment strategy (as we plan the government laughs).

HSA Providers and Account Costs

There are quite a few HSA providers, but the expense breakdown usually follows a similar formula. The HSA provider has a banking side and an investment side. There is a $2.50 per-month fee if the banking side doesn't maintain a balance over $5,000. This fee amounts to 0.6% of the $5,000, which I believe the investments will outperform over time. This means, it makes sense to pay the fee rather than keep the cash on the bank account side. There is also the underlying investment fund fee, which can be minimized by using the link to a brokerage firm (if the HSA provider has one) to invest in a much wider variety of funds available than under their standard list of investment options. This allows the account to be linked to an Evensky & Katz portfolio to make the most of tax-sheltering assets that would otherwise create a high percentage of tax liability in the portfolio. There would also be a $3 per-month fee if your investment account drops below $5,000, along with any number of fees attributable to things such as closing the account closure, ordering a checkbook, ordering a debit card, and so on.

It's crucial to know how you plan on using the HSA account and make sure you have the best supplier for your needs based on fees and investment options.

Special Considerations

If the spouse is the beneficiary of the HSA, it will be treated as the spouse's HSA after your death. If the spouse isn't the beneficiary, however, the account stops being an HSA, and the fair market value minus any qualified medical expenses for the person who passed that are paid by the beneficiary within one year after the date of death become taxable to the beneficiary in the year in which the account owner dies.

One HSA rollover is allowed per year within 60 days of receipt, but the rollover is not limited in terms of the amount of money rolled over.12 This means you can briefly tap into HSA funds in an emergency as long as you can pay it back within 60 days. Any amount not rolled back into an HSA account will be taxed, and penalties could be charged.

If employers offer HSA funding through a cafeteria plan payroll deduction, it is generally not subject to FICA taxes that go to Social Security and Medicare, which generally amount to about 7.65% of the amount contributed by payroll deduction. This means that absent a better use of your employer cafeteria deduction amount, it can be even more profitable than usual to fund your HSA plan with as much of the cafeteria plan funds as possible.

A qualified HSA funding distribution from an IRA to your HSA can be made once during your life. It reduces the amount you can contribute to the HSA that year by the amount converted. This means, in a year in which you can't afford to fully fund your HSA from your income and savings, you can fund it with IRA money. If you have saved up sufficient health receipts and you had the HSA open during the proper period, you may be able to reimburse yourself for past expenses with the current value of the account. The money must pass directly from the IRA trustee to the HSA, and it isn't included in income or deductible. This can be done from a Roth, but that generally wouldn't make sense since you would be putting money you have already paid taxes on into an account you may have to pay taxes on (if not used for medical expenses). The qualified funding distribution can't be more than any amount you are entitled to contribute to an HSA that year. You must also remain a qualified individual for 12 months after this transaction takes place, which means your insurance or qualifying insurance must remain in place for 12 months after the money is moved.

This one-time funding of your HSA from your IRA can be beneficial for years in which you can't fund an HSA, especially if you would otherwise need to tap into your IRA for living expenses (which would cause you to pay taxes and possibly a penalty). Depending on the situation, you may be able to fund the HSA with your IRA funds and then reimburse yourself for past medical expenses from the money now in your HSA, doing away with both the early withdrawal penalty and taxes associated with the withdrawal.

Some HSA Rules

  * HSA distributions prior to age 65 for people who are not disabled for non-healthcare qualified expenses are charged ordinary income tax plus a 20% penalty.
  * An HSA can be funded by an individual, an employer, or a combination of the two. You don't have to use the employer-provided HSA provider unless your employer requires you to maintain an account with them to receive employer contributions. Once the employer contributions are received, they can generally be transferred to your preferred HSA provider (you can have multiple HSA accounts). Any contributions are tax deductible (even if the tax return does not itemize deductions) but keep in mind that the IRS does not see employer contributions as income, which means they are not taxed to begin with and so cannot be deducted.
  * Funding an HSA requires a high-deductible health plan, and the person for whom the account is titled can't be claimed as a dependent on someone else's tax return for the year. In 2018, a high-deductible health plan has a minimum annual in-network deductible of at least $1,350 for an individual or $2,700 for a family and a maximum annual in-network deductible of $6,650 for an individual or $13,300 for a family.13
  * Contributions are limited to a combined funding limit of $3,450 per year for an individual or $6,900 per year for a family in 2018, but remember that the funding levels cover total funding among all HSA accounts, including any Archer MSA accounts. Anyone over the age of 55 can contribute an additional $1,000 per year, which means an individual over 55 can contribute $4,450 and a family with two eligible spouses over 55 years old can contribute $8,900 for 2018.14
  * You (or your family) are eligible for the entire year if you are eligible on the first day of the last month of your tax year (which is December 1st for most taxpayers) even if your spouse has a non-high deductible health plan, as long as the non-HDHP doesn't cover you. However, there may be some limitations to how much you can contribute, and you may be required to keep the health plan or other qualifying health plan for 12 months to ensure that the HSA contributions are not included in the next year's income with a penalty.

  * There are other rules to determine eligibility. If you have any questions regarding your eligibility, you should speak with your financial advisor or accountant. Contributions to an HSA can be made until the tax filing deadline for the year, which is usually April 15 of the following year.

  * You do not have to be eligible to save in an HSA account or have a high-deductible healthcare plan to use previously saved HSA money for health expenses tax free. Any money you save in the HSA does not go away at the end of the year. HSA funds roll over and accumulate from year to year (unlike funds in FSAs) and remain in your account if you leave your employer (unlike company-owned Health Reimbursement Accounts).
  * You cannot use HSA money for health expenses that will be reimbursed by your health insurance and still have the HSA distributions count as qualified tax-free distributions. You also can't deduct medical expenses you have used HSA funds to pay for. You must keep all pertinent records for any HSA distributions, including receipts and proof that the expenses weren't paid for by a medical plan, reimbursed from another source, or taken as an itemized deduction in any year.
  * Qualified medical expenses are generally expenses your insurance would cover if your deductible had been met that were incurred after you qualified for and established your HSA.
  * You generally can't use the account to pledge for a loan or buy goods and collectibles without risking the amount used being deemed as distributed for non-qualified medical expenses for the year and fully taxed with potential penalties (although there are some exceptions).
  * Any distributions the HSA owner takes by mistake having reasonably believed they were for a qualifying medical expense can avoid tax consequences by returning the funds to the HSA before April 15th of the year after they discover the mistake.
  * For employers, the amount contributed to employees' HSAs aren't generally subject to employment taxes, although there are non-discrimination rules stating that all employees in the same class must receive HSA contributions (if any employees receive HSA contributions) to avoid an excise tax of 35% on contributions. This may mean employers strategically classify full-time and part-time workers, individual and family participants, and employees who are or are not enrolled in high-deductible health plans.

## Flexible Spending Account

FSAs allow you to put away money before taxes to pay for medical expenses. You may be able to set aside money every year to use pre-tax dollars for your insurance copays, deductibles, some drugs, and certain other healthcare costs. However, remember that an FSA is a use-it-or-lose-it arrangement, which means you generally must use all or the vast majority of the funds within a certain time frame, generally by the end of the year.

Medical FSAs put all the employee's annual contributions in at the start of the plan year. The employee can elect to defer a certain amount of money, spend the account down, or leave the employer for another employer without actually saving the amount of money from their paycheck withholdings that they've spent on tax-free medical expenses.

Strategies

If the plan allows the rollover of a certain amount of money, it is almost always recommended to fund the FSA with at least the amount you can roll over from one year to the next to take advantage of the tax savings as long as you have the excess cash flow to afford to do so. Keep in mind that this money may go away if there is a separation from service with your employer, so it can be very important to spend down an FSA before quitting or being terminated from your employer.

If you decide to use an FSA, make sure you know how you'll spend any extra money at the end of the year, including getting an additional pair of glasses, having dental work you might not otherwise have done, or buying medical equipment you need or know you will need. If you find you are getting close to the end of your plan year and you have money left in the plan you will not spend, it is worthwhile to go on websites that cater to FSAs to see what you may need that is available rather than losing the money when the plan year ends.

Remember that there may also be requirements to apply for refunds or reimbursements from the plan, so the dates of those filings should be noted and followed strictly.

Contributions

Employers can make contributions to your FSA, but they are not required to. FSAs are limited to $2,650 per year per employee; if you're married, your spouse can also put up to $2,650 in an FSA with their employer.15 FSA funds can be used to pay for not only your medical expenses but also medical expenses for your spouse and dependents. The funds cannot be used to pay for insurance premiums. The funds can be used for over-the-counter medicines with a doctor's prescription (although insulin is allowed without a doctor's prescription). They may also cover the cost of medical equipment.

Money put into your FSA by your employer that is not deducted from your wages is generally not counted against the FSA funding limit for the year. This means that if your employer contributes $1,000 to your FSA, you are generally still allowed to contribute the full $2,650 per year to your FSA. An exception to this would be if your employer's FSA contribution comes from your employee benefits cafeteria plan, in which case your employer benefits would reduce the amount you can put into your FSA to a combined $2,650. In addition, if you have multiple employers offering FSAs, you may elect to defer an amount up to the limit under each employer's plan; this differs from HSAs and IRAs, which only allow the combined funding up to a certain limit no matter how many accounts or employers you have.

Depending on the FSA, you may be allowed a grace period of up to two and a half extra months to use the money in the account or a carryover to the next year of up to $500. Only one of these options can be offered, and plans aren't required to offer either one.

Carrying over a certain amount of money does not reduce the participant's maximum FSA contribution for the next plan year. So, someone who carries over $500 from one plan year to the next can still contribute the maximum for the next plan year so they can get reimbursed for more than just the plan maximum for the next year.

Rules and Tax Implications

Generally, the money put into an FSA is not only exempt from your regular taxes but also not subject to payroll taxes for Medicare, Social Security, and Medicaid. This leads to an even higher tax savings than many other ways of saving money in a tax-benefited savings vehicle.

People who have high-deductible health plans with HSAs they are eligible to fund are generally not allowed to also have FSAs, except for a limited-expense FSA, which is also called a limited-purpose FSA account. This type of FSA can be used to reimburse dental and vision expenses as well as potentially eligible medical expenses incurred after the health plan deductible is met; however, it is important to understand the details of how this works for your particular plan before thinking about funding it with anything above the amount that can be rolled over or that you know you will need during the plan year. You may be able to extend your ability to keep your FSA money after you are laid off if you continue health coverage under the company's COBRA health insurance or another arrangement.

In addition, there may be multiple types of FSAs offered through your employer, such as health and dependent care, but generally speaking, the money cannot be transferred from one type of account to another.

## Dental Insurance

The cost of all types of health coverage has been on the rise, and dental insurance is no exception. In fact, dental care is not only more expensive, but employers are now putting more of the costs of dental insurance on their employees. This means it's important to shop around before defaulting to your employer's plan since you may find that an organization you belong to provides a plan that better fits your needs (e.g., professional organizations, AARP, and many other organizations offer group dental plans).

When comparing dental plans, it is important to not only look at cost but also make sure your dentist is considered in-network; if not, consider whether you are willing to switch to another dentist in the dental plan's network. Dentists outside the plan may provide you with little to none of the plan benefits.

You may see dental plans list coverage with three numbers illustrating the percentage of particular services the plan will cover (100-80-50 plan). These numbers can be understood as follows:

  * 100: The plan covers 100% of preventative dental work, including regular check-ups and cleanings.
  * 80: The plan covers 80% of the cost for common dental procedures the plan covers. Common procedures include cavity fillings, braces, root canals, whitening, etc.
  * 50: The plan covers 50% of the cost for major dental procedures the plan covers. Major procedures include tooth crowning, tooth implants, procedures requiring sedation, etc.

Typically, plans will require you to pay a small deductible. They will cover a certain percentage of costs after the deductible has been met, depending on the category in which the procedure falls, up to a yearly cap, after which point you will have to pay all remaining costs.

## Vision Insurance

Vision insurance commonly pays for the following:

  * Preventive care, including annual eye exams and check-ups;
  * Costs associated with contact lenses, lens frames, lenses, and lens protection methods;
  * Disposable contacts (typically an added coverage that costs more); and
  * Eye surgery discounts (typically an added coverage that costs more).

It's important to note that it's not uncommon for vision insurance providers to deny coverage for medical issues related to your vision. Should something come up during a check-up, your doctor will likely refer you to a specialist, the costs for which wouldn't be covered by your vision insurance. The good news is that although vision insurance may not cover the cost of such medical issues, your health insurance would cover the costs more often than not.

Some important questions to ask yourself and your employer regarding your vision insurance include the following:

  * Does your vision insurance cover the costs of eye tests or exams you want or need?
  * Does your vision insurance cover the costs of glasses you want or need?
  * Does your vision insurance cover the costs of lenses you want or need?
  * Are you required to go to a low-cost chain store, or can you go to your private practice doctor?

## Life Insurance/Accidental Death and Dismemberment

Life insurance offered through your employer is often a very good deal. Because the underwriting is done for the employer as a whole, it's generally low cost; it may even be free. Signing up is easy since you are generally not required to undergo a physical exam to qualify, and it's usually pretty inexpensive. The problem is that a person can often buy a limited amount of insurance through their employer's plan, which may not be enough to cover the amount of life insurance you need.

How much life insurance is necessary?

Life insurance is looked at as an income replacement insurance plan in case someone passes away. To find the minimum amount of coverage you should have, figure out how much it would cost for your family to live without your income and replace that amount minus any growth on the assets you think they'll receive. This involves thinking about things like additional childcare and someone to help around the house. It can help to figure out how much it costs for you to live currently and how much each partner earns, although the lifestyle costs may increase or decrease depending on the family dynamic.

As a very rough starting point, if you are the sole breadwinner, it is generally recommended to make sure your assets minus your house add up to at least roughly 20 times your yearly expenses (you should speak with your financial planner and insurance provider for a specific recommendation). If your assets do not add up to 20 times your yearly expenses, then the current amount of shortfall is a very easy way to gauge the least amount of life insurance you should purchase from your employer or other life insurance program if possible.

Change of Employment Status

Another important point to make about employer life insurance is that you may lose life insurance if you quit your job or get fired from your job. You may be unable to get private insurance, and your next employer may not offer insurance. Some employer-sponsored life insurance plans are portable, so you can take them with you if you leave the job, but it's important to know what type of life insurance your employer offers so you can buy insurance on the open market if your employer does not provide enough or the right type of life insurance.

## Short and Long-Term Disability Insurance

According to the Social Security Administration16 one in four people in their 20s working today will become disabled before retirement age. One way to hedge against a disability is via disability insurance, which gives you a portion of your pay if you can no longer work for a specific period. The cost of disability insurance through your employer is often very inexpensive, making it worth considering. A disability can be due to pregnancy, short-term illness, or long-term illness.

Strategies and Tax Implications

It is important to know how to structure the payments for your disability insurance. If you pay for disability insurance with FSA funds or other pre-tax dollars, you will have to pay taxes on the benefits if or when you use the disability insurance. If you pay for the disability insurance with after-tax dollars, the benefit will be tax free. Given that the disability insurance only covers a percentage of your pay, it's generally advisable to use after-tax dollars to fund the benefits. Personal circumstances, such as an inability to fund with after-tax dollars or to gather funds to cover any shortfall between the cost of living and the after-tax value of your disability benefits in case of a disability, may change the calculation for which option is most beneficial to you.

If your employer pays for your coverage pre-tax, your benefits will be taxable.

## Critical Illness Insurance

Critical illness insurance pays out a lump sum if the employee gets cancer or another serious illness. The insurance may be part of a cafeteria plan in which you choose how much money goes to which benefits, you may have to pay for the insurance out of withholding from your paycheck, or your employer may pay for the coverage. Remember that the benefits generally will not be taxed if the employee pays the full premium with after-tax money, whereas the lump sum payments will be taxed if the employer pays the cost with pre-tax money.

Coverage and Cost

The policy can be small or can cover as much as a million dollars per issue. So, it's important to know how much coverage you need in coordination with any long-term care and disability insurance should you contract a major illness. Different policies cover different things, including:

  * Heart attack
  * Cancer
  * Heart transplants
  * Coronary bypass surgery
  * Parkinson's disease
  * Alzheimer's
  * Amyotrophic lateral sclerosis
  * Loss of sight
  * Loss of speech
  * Loss of vision
  * Heart valve replacement
  * Angioplasty
  * Kidney failure
  * Major organ transplant
  * Stroke
  * Paralysis

Keep in mind that each of these illnesses must meet the specific definition of the illness from the insurer; some cancers, strokes, etc. that you think will qualify don't in fact qualify for a payout or only qualify for a partial payment. Likewise, some policies may require you to see a specialist in the particular field of your illness to qualify as having the disease properly diagnosed. So, it is important to know what your insurance actually covers.

It is often wise to consider disability, long-term care, and life insurance as the first places for insurance coverage money to be placed before looking at critical illness insurance. Keep in mind that self-insuring runs the risk that you contract a critical illness early on in life (in which case the insurance would have paid a significant return). If you do need coverage, this type of insurance can be very beneficial since the lump sum can be used to pay for things that aren't covered by insurance, such as:

  * Some of your pay while not working
  * Travel costs to specialists
  * Specialists not covered by insurance
  * Experimental treatments not covered
  * Replacement of spouse's income while they care for you
  * Health insurance premiums while you're not working
  * Time off work
  * Out-of-network doctors & hospitals
  * Rent & Utilities
  * Mortgage & real estate taxes
  * Credit card bills
  * School tuition
  * Food

Insurers may provide up to a certain amount through your employer without going through a medical exam; however, amounts over that limit will require a physical. It's important to make sure a failed health exam will not preclude you from getting the employer's group coverage with no underwriting. To ensure that you're protected in this scenario, you want to max out the available employer group coverage without underwriting while going through the underwriting just in case you fail the health exam and can't get anything above the group coverage if that strategy is possible. Whether you go through your employer or an open-market plan from an insurance broker, you don't want them to find cancer during underwriting, thus disqualifying you for any coverage, when you could have taken advantage of the group coverage prior to having the physical and finding out about the medical ailment. The group coverage will often require you to answer a few questions before providing the coverage you want.

Generally speaking, it is better to prioritize life insurance and disability coverage and then look to critical illness insurance since it is narrower in scope and it can be expensive. Of course, this changes for very cheap or free coverage or if your family has a medical history of critical illnesses. It is important to consider this in the hierarchy of insurance needs and decide where to spend your dollars to get the most benefit in terms of coverage and the way things will affect your life. I recommend speaking to a financial planner and insurance agent before making any decisions. The coverage may include only you or cover your spouse or domestic partner, your children, or family, so is important to know who can be covered and make sure you have thought about an objective for the appropriate coverage.

What the insurance covers can be very specific, so it's important to know all the terms of the contract. Are pre-existing conditions covered? Which types of cancers and heart attacks are covered? Are some treatment payouts only partially covered, such as certain treatments for heart issues or cancers? Can you get a one-time payout or can you receive payments multiple times for the same illness or different illnesses over time? Do the policies require that you be hospitalized or receive chemotherapy or radiation to qualify? Is there an age-related benefit deduction (i.e., as you grow older, will the benefits decrease)? Is the policy portable (i.e., what happens if you switch jobs, retire, get laid off, or get fired)?

Payout Policy

Some policies provide multiple cash payments, such as for someone who has a heart attack followed by a kidney transplant, so the insurance will make multiple payouts from the same policy. On the other hand, some policies will only give a single payout for the first of the two issues. In addition, some policies will grant a second payout for a second occurrence of the same event, such as the second occurrence of a heart attack, although the second payout may be lower.

You may find that different illnesses provide different payouts as a percentage of the full value of the coverage (i.e., some cancers may pay out 100% while other cancers pay out 25%; skin cancer pays out a flat rate far lower that is not tied to the total coverage amount). There may also be a requirement that a certain amount of bodily damage be done in addition to the disease diagnosis to qualify for a payment.

The coverage may also provide an additional stipend for certain treatments, transportation, or lodging in association with the covered illness. Likewise, lifestyle choices, such as drug use, flying small planes, alcohol abuse, being part of a war or riot, or self-inflicted injuries, or how the illness was acquired may change your coverage. Some insurers require you to live for a certain period after a diagnosis, so someone who has a heart attack but dies the next week may not be covered for a payout under the policy.

# Highly Compensated Employees and Executive Benefits

Deferred Compensation Plans

Capital Accounts

## Deferred Compensation Plans

Deferred compensation is a written agreement between an employer and employee in which the employee voluntarily agrees to have part of their pay withheld by the company, invested on their behalf, and then given to the employee at a predefined time in the future. This allows the employee to potentially defer paying taxes on money earned until the employee is in a more preferable tax environment. Employees must pay taxes on deferred compensation at the time they are eligible to receive it and not when they draw it out.

You generally want to think about a nonqualified deferred compensation plan contribution as an unsecured loan between you as the employee and the employer, in which you lend your employer the amount of money based on the agreement that your employer will pay you that amount of money plus any earnings subject to the investment or a fixed stated rate of return at a certain point in time. Some employers may be worthy of this loan, while other employers are unlikely to pay it back; you must consider this reliability before you elect to contribute to a nonqualified deferred compensation plan.

Strategies and Timing

Deferred compensation can be significantly beneficial, especially when used in tandem with other employee benefits such as RSUs. The employee can sell the vested RSUs they would have to pay ordinary income tax on in that year anyway and live off the proceeds while deferring their regular wages in a retirement account, deferred compensation account, or other tax-deferred savings account.

The employee can also defer ordinary compensation (potentially until after they have left the employer) so they receive ordinary income during a period in which they might not receive any income, thus lowering the amount they are being taxed on during their working years. Although this can be very beneficial, it is not without risk, specifically employer-specific risk. This risk is realized when the employee participating in a deferred compensation plan is working for a company that declares bankruptcy or goes out of business. In this scenario, the employee is standing in line with other creditors of the business to collect on any portion of the deferred compensation plan they can during the bankruptcy proceedings.

You may also think about participating in the deferred compensation plan if you are on the border of receiving a financial aid award for children going to college, which can lower your income in the eyes of financial aid offices. This allows your children to potentially receive some financial aid that they might not otherwise receive. Furthermore, if you are involved or potentially involved in litigation, it may be worthwhile to put some of your assets into a deferred compensation plan since lawyers may be more focused on assets available now rather than money that will be available at some point in the future.

Typically, an employee chooses how much they would like to defer; any payout terms, including amounts in a period; or triggering event. When opting for the deferred compensation plan with little flexibility to change these options in the future, it is important to not only think about your current tax, income, and expense situation but also plan for the future to make sure you've done your best so it is unlikely that you will need to make any changes to the plan later.

It is also important to remember that the money is at risk any time it is held in the plan so you do not defer compensation for too long; the longer the money sits in the plan, the riskier it becomes. The deferred compensation amount also becomes larger, and what is known about your company now and for the next year may certainly change 10, 15, or 20 years down the road.

It's generally recommended to make the maximum contributions to a retirement plan before thinking about enrolling in a nonqualified deferred compensation plan. There is a tax benefit to contributing to your retirement plan and the potential to take loans out of the retirement plan along with a potential match from your employer and protection from your employer's bankruptcy. You generally have the ability to choose how much to defer from your salary bonuses and other forms of compensation every year, so some changes can be made.

Plan Portfolio and Risk

You may be able to guide the investment broadly in the deferred compensation plan, but you will generally be unable to make precise investments, such as choosing individual stocks to invest in, during the time it is invested for your benefit. However, you may be allowed to direct what percentage of your money goes into specific allocations of funds, such as how much goes into U.S. stocks vs. international stocks or into stocks vs. bonds.

Rather than allowing employees to invest money in the deferred compensation plan, some companies may pay a fixed or variable amount of interest on that deferred money, which may be a benefit in and of itself if you don't need to live off the income. You may end up getting a higher percentage guaranteed return from the deferred compensation plan than you would expect to receive from a portfolio based on your risk profile (keeping in mind that putting the money in a deferred compensation plan certainly overexposes you to a single company by essentially accepting an IOU from your employer).

Tax Implications

When looking at your tax situation, it's important to not only consider federal taxes and Medicare but also whether you plan to move from a high-tax state to one with low or no state income taxes or vice versa. In other words, if you move from a state like California, which has high income taxes, to one like Texas, which has no income taxes, you may be better off receiving the income while you live in Texas than while you live in California even if your federal tax rate remains the same. Likewise, if you plan on moving from Texas to California, it may be worth thinking about not participating in the deferred compensation plan even if your federal tax bracket will be lower in California. The difference between the lack of state taxes in Texas compared to the state taxes that will be due in California may push you into a higher overall tax bracket, meaning that it is worthwhile to receive the money while you are in a higher federal tax bracket while working in Texas—plus, you have the added benefit of not having to deal with the company-specific risk.

It is not necessarily the case that your tax rate will decrease during retirement even if the tax law stays the same since you may have Social Security earnings, required minimum distributions, and pensions, which could take you into a similar or higher tax rate than what you had during your working years. In that case, it may not be worthwhile to participate in a deferred compensation plan, especially given the company-specific risk you would be taking with both the deferred compensation plan and your earning power as an employed worker if your employer goes out of business.

As always, tax laws can and will change, and we may see income taxes rise in the future. This means that, even if you personally earn less money since it slowly comes through the deferred compensation payout at a lower rate than what you earned during your working years, that money may still be taxable in a higher bracket because the tax brackets have changed. As such, it is important to at least be aware of the risks faced by deferring compensation.

Remember that you may be able to receive a higher rate of return on the money if you can invest it in any way you want compared to the rate of return your employer's investment options will provide you. This is very clearly a case of not letting the "tax tail wag the dog" and deciding whether it is worth accepting a lower rate of return for a lower tax bill or worth paying the taxes immediately and receiving the higher rate of return on your investments without being overexposed to individual company risk. The plan's investment options may be limited to insurance options and fixed percentage return, or it may have limited investment options with high expenses.

Keep in mind that you will have to pay Social Security and Medicare taxes on any amount you choose to defer in the year in which it is deferred. This may mean that if you defer the money and your employer declares bankruptcy, you may not receive the money that was deferred, and you may have paid Social Security and Medicare taxes on that money in the past.

Plan Payout

As with everything that has a value for which it is possible to name a beneficiary, it is wise to speak with your HR department about naming a beneficiary on any deferred compensation plans just in case something happens to you while you are participating. The purpose of naming a beneficiary in this context is so your money will go directly to your beneficiaries rather than through probate.

Keep in mind that some circumstances can force you to realize the entirety of your deferred compensation plan payout earlier than you intended, pushing you into a higher-than-normal tax bracket. Such circumstances include being terminated from employment, passing away, or your company being acquired. This may force you to realize the entirety of your deferred compensation while you are still work. Hence, it is important to understand all the risks you face along with any potential changes to your employer before opting for a deferred compensation plan, even if doing so can be very profitable under the right circumstances.

When enrolling in the plan, it's important to consider the distribution schedule your employer allows. Do they require you to take the payment as a lump sum distribution so your income is much higher for a single year than it would normally be, pushing you into a very high tax bracket when you would ordinarily not be in that tax bracket, or can you take money added over several years? Are you allowed to take money out of the plans before retirement, or do you have to wait until retirement? All these details should be laid out in the plan document, which will list the payment schedule and the event that will trigger the payments, every time the amount is deferred. Possible triggering events are a fixed date, a separation from service, a change in ownership or control of the company, disability, death, or an unforeseen emergency. This means that, it can be very important to monitor the health of the company you're employed by so you know what may happen to your deferred compensation plan and then plan accordingly. You may find yourself in a position where you know the company finds itself on weak financial straits (which is not a triggering event) so you know you will be likely to have to attempt to get your deferred compensation through your employer's bankruptcy proceedings if you stay with the company. With this knowledge, you can strategically retire or separate from service so you may be able to remove the deferred compensation from the plan before your employer goes bankrupt and not lose all or significant portion of your money.

Keep in mind that a nonqualified deferred compensation plan may also impose conditions on receiving the money, such as a non-compete agreement after retirement, so any decisions to change employer after separation from service can cause a claw back of the money in the nonqualified deferred compensation plan. Depending on how the deferred compensation program is written, you may end up forfeiting all or part of your deferred compensation by leaving the company early, which means you leave a substantial amount of money on the table.

Unlike a 401(k), you cannot take a loan from a nonqualified deferred compensation plan, and the funds are not accessible before the designated distribution event. In some cases, you may be able to change the election for when you will receive the deferred compensation. However, these changes must generally be made at least 12 months before the date on which the original payment is scheduled to begin, the election must delay the payment for at least five years from the previously scheduled payment date, and the election will not be effective until at least 12 months after it is made. This means that if you previously decided to retire at age 60 and you receive your nonqualified deferred compensation but decide to continue working until age 65, you may be able to extend the length of your nonqualified deferred compensation payout by the age of 59, 12 months before you turn 60 and are previously scheduled to receive the payout. So, you receive the payout at age 65 when you now intend to retire.

## Capital Accounts

Capital accounts are the initial and subsequent contributions by partners to a partnership in the form of cash, assets, or profits as well as losses earned by the business and allocated to partners. The amount of money you get from liquidating your capital account does not necessarily equate to the reported balance of the account (whether prior to the business's liquidation or the partner's departure from the firm). Capital contributions can be variably based off a set amount of partner contribution tiers determined by years of service, the level of compensation, or the amount of equity you have in the firm.

Potential Advantages

Capital accounts can be very beneficial for employers and partners. The employer gets to show an asset on the books as long as it is kept in the books and not directly spent or distributed to partners with ownership shares. The company does not need to go to a bank for a loan when they can rely on partners for a loan. In addition, partners will often not closely look at the books—or not be allowed to look deeply into the books—before deciding whether the company is creditworthy. That being said, the interest rate given by the employer can be very enticing, and if the employer is stable, it can be very profitable for the partners who contribute to a capital account.

Like many things, this can be used for good or evil. The employer can get a loan cheaper from its worker than a bank, and the partner is less likely to have the ability to put the employer's financials through a thorough underwriting process. It can be a win–win or a very one-sided affair, so it's important to know whether you're putting skin in the game or getting skinned.

Potential Risks

When contributing to a capital account, it is important to realize that in essence, you are giving an unsecured loan to your employer or partnership; thus, you are subject to the risk associated with loaning your company money. This is often seen as ownership in a partnership, but in reality, a number of capital accounts arrangements are calculated by way of a formula rather than as a true ownership in the partnership. This means your capital contributions may have a fixed valuation when you want to withdraw from the capital account, and they may earn a fixed interest rate or none at all while the money is held in the capital account (rather than giving you participation in the upside of the business's growth). It's not uncommon for the employee to receive a rate of interest tied to the return of some benchmark.

Your capital could be used to fund the short-term needs of the company or to shore up unsustainable distribution levels for partners. This may make the proposition look appealing in the short term, but it can have long-term consequences, similar to a Ponzi scheme held up by bringing in new partners' capital and the ongoing operating cash flow of the business. In such a case, the capital account slowly destroys the firm for the benefit of a few people, and it's a matter of getting your money out before the ship sinks.

Another important question to ask is whether the capital money being contributed is being used to run the business so no debt is taken on or if it is being wasted on bad decisions, expansions by management, or equity partner distributions that are higher than they should be. In other words, having funds in capital accounts can spur management to need to deploy the funds in investments, which in turn creates additional risk rather than shoring up the balance sheet.

Remember that the firm can find itself at a point where the equity partners making the decisions have the choice whether to continue an unsustainable path or to correct the path the firm is on. Under some circumstances, it may be in the best interests of the equity partners to continue on the destructive path and then jumping with their client base and starting over at a new firm. This may be substantially more lucrative to them than correcting the problems at the existing firm, which in turn makes the equity partnership look less valuable. Similarly, some partners in leadership positions have income levels that are well above what their book of business would be worth if they were to relocate, which means they can't replace their income if they leave for another firm. This means the, the leaders at the firm may decide to continue the status quo to serve their best interests rather than serving the interests of the firm, and even if they wanted to, they be unable to change the firm's business model due to the fiscal or political environment. So, remember that while this may often be very beneficial, in some cases it is less risky and more profitable for a firm's leadership to allow the firm to sink rather than save it. So, any capital accounts kept above the minimum account balance required by the firm should be well researched, thought out, and debated before any decision is made to contribute. It's also important to note that the firm may have a model for calculating partners' capital accounts upon departure, and the liquidation of a firm may not provide sufficient liquidity to pay out all partners' capital accounts in full.

The economic environment is also an important factor to keep an eye on. Even a well-run firm can run into problems during a sharp downturn since the ability to get partner capital during a financial crisis can come when business is slow, banks aren't lending to firms, and there is increased weakness in financials; this all happens at a time when the dollar opportunity cost is high for the partner who contributes and the employer that needs money to continue running the business. This can mean some partners become hesitant to throw good money after bad in a downturn so they decide to invest elsewhere, causing a larger-than-normal need for a business that was otherwise sustainable.

Key Considerations and Regulations

It is very important to know the terms that govern the return of your capital. It's not uncommon for a firm to stretch out the period during which it will return capital to any departing partner. The firm may also have a period during which you will not be allowed a return of your capital if you take a job at a rival firm. You may also have a vesting period; during that time, if you leave or something happens to you, you may not get a return of capital even if you do not work for a competitor once you leave. It's also important to know what happens to your capital account if you get let go.

Make sure you understand whether you have any equity interest in the firm as a partner or if you have explicitly waived your interest in the form of equity and agreed to essentially be a partner providing a cheap loan to the equity partners. In other words, is the value of becoming a partner worth the amount contributed since your money may be gone the moment it's contributed?

When looking at the financials of a partnership, it's important to consider that the liabilities encompass not only the direct liabilities we think of, like loans and capital contributions, but also things like leases on furnishings, equipment, and real property. All these can add up to a significant level of leverage across the firm. This means, a company with no debt may still have a substantial financial risk.

It's also important to know whether buying into the partnership will reduce your take-home pay and, if so, to account for that reduction in any decision of whether to be a partner in a firm that requires capital calls.

You may also find that high-ranking partners have special agreements to raise their flexibility in terms of partner capital, such as the ability to draw on non-interest-bearing loans, credit distributions against future draws, or guaranteed minimum distribution amounts.

# Quality of Life

Time-off/Sabbatical Policy

Paid Time Off, Vacation, and Sick Leave

Flextime

Work From Home

Travel Related Expenses

Dependent Daycare Expenses

Housing

Student Loan Repayment

Financial Advisor Fee Payment

Relocation Assistance

Legal Plan

Volunteer and Gift Matching

Tuition Reimbursement or Assistance

Employee Assistance Programs

Adoption Assistance

Family Caregiver, Maternal, and Paternal Leave

Military Leave

Discounts and Special Programs

## Time-off/Sabbatical Policy

Time off for sabbaticals may be paid or unpaid depending on the employer, the duration of service, and the type of service (i.e., full or part time). Taking a sabbatical can be beneficial both in the short and long term for both the employee and the employer. The employee can return to work with an overall sense of well-being, having recharged their batteries and stepped away from the day-to-day grind of working, allowing them to come back with long-term positive changes to thinking and creativity. While an employee is typically more inclined to check in with work during a vacation, a sabbatical may provide the employee the ability to "check out" of the office for one to three months. This also gives the organization time to make sure the other employees have been properly cross-trained to ensure that the organization would be stable if they lose any employee.

Benefits

Planning for a sabbatical should begin far in advance by cross-training the other people in your department. This can be a learning experience for everyone involved, leading to a stronger organization overall. The people who are cross-trained to fill in for the employee while the employee is on sabbatical can become more effective and responsible by the time the sabbatical taker returns because they can see the organization from a different viewpoint and gain wider experience working within the organization. Employees may find creative ways to grow the business that they would not have otherwise been inspired to pursue had they not spent time away from the company seeing things from the outside or from a different cultural viewpoint. Ideally, no team should be so dependent on any one person that everything falls apart if that person leaves, and a sabbatical is an easy way to test that.

The sabbatical also gives the individual a chance to view themselves and the world around them from a new direction, take on a new project, volunteer for something they care about, do research, write a book, learn a new language, pick up a hobby, reconnect with friends, work on a passion project, explore new ideas, travel, improve their health, spend time on their retirement or estate planning, take care of their family, or learn something new. All these activities lead to a better mental state upon the employee's return to work and their ability to concentrate on the work in front of them since they have already taken care of the personal things that they had either put off or that were weighing them down during the work day. An employee coming back from a sabbatical often feels rejuvenated, like they have a new job, and no longer shows signs of burnout, returning with renewed focus on their work and sense of purpose.

A sabbatical can also be a great time for employees not on sabbatical to step forward and act in the role of the person on sabbatical by gaining valuable experience and showing management that they have the ability to step into that role if that position becomes available. Extra work taken on during a coworker's sabbatical should be seen as an opportunity to be trained in a new area and to achieve expanded potential within an organization.

It may be wise to consider taking a sabbatical before leaving a company since your desire to leave the company may be a sign of burnout rather than an issue with the company. Used properly, the sabbatical can not only change your life but also provide valuable insight for your firm and a renewed sense of vigor to push through to the next level of your career.

Planning

A sabbatical is not like a typical vacation in that you only need to spend a short period preparing the office for a vacation. The planning for a sabbatical should start a year or years beforehand so cross-training is thoroughly done and everything is thought through and planned far in advance of the sabbatical. Always be thoughtful when scheduling and coordinating your sabbatical so you do not wind up with multiple people out of the office, placing stress on the employer and employees who remain to cover multiple shifts rather than just yours.

If your sabbatical is thoroughly prepared for, you may find that rather than coming back to a desk full of work, you come back to employees who are more self-reliant and accustomed to solving problems, having taken care of everything in your absence. If things are handled well during your absence, you can see that you don't need to micromanage people and rely more heavily on your coworkers and subordinates. On the other hand, if you come back and things have fallen through the cracks that were an employee's responsibility, you can get further insight into that employee's capabilities and shine a light on their work in their current position, ultimately affecting their further employment or promotion opportunities in the future.

Some employers will allow you to combine your leave with your paid time off, whereas some will not. In general, paid time off and sabbatical policies are based on an employee's tenure with the employer. Make sure you know what will happen to your health benefits while you are on leave so you know if you will need to pay for health benefits, if your employer will pay for the health benefits, and whether FSA or dependent care accounts will stay in place. You'll need to know if your job will be available upon your return and if there is there a penalty for failure to return to work (either monetary or through a complication in benefits).

Before taking a sabbatical, it's important to make sure you are financially ready and secure to cover your living expenses for the time you are away if it is not a paid sabbatical. It may be possible to split your sabbatical in two or combine the sabbatical with PTO to extend the time you can be gone. You will also need to note the effect the sabbatical has on all your benefits, including health benefits; retirement savings (including 401(k) contributions and matches or pension years of service in your pension calculation as taking an unpaid sabbatical during the last three years of employment if your pension is based off your last three years of salary can cause significant long-term detrimental effects); and insurance coverage, such as life insurance and disability insurance.

It's also important to know whether you can take a paid job during your sabbatical since your company may limit you to not taking paid positions; if you are allowed to take a paid position, you may be restricted from working at a competitor's firm. In addition, note that it is important to know whether anything you produce during your sabbatical will be considered your employer's intellectual property.

## Paid Time Off, Vacation, and Sick Leave

Paid time off (PTO) can be a specific number of days per year after a certain number of years of service, or you can be given a certain number of PTO hours per hours worked as a credit towards the number of hours in a bank you can use. Most PTO expires at the end of a certain period, but occasionally employers will allow you to roll PTO over from year to year. There may even be an opportunity to sell your PTO days back to your employer at certain periods, such as banking PTO days throughout your career and selling back a large block of them to your employer before retirement.

PTO vs. Vacation and Sick Days

Employers generally have vesting periods for employees to start PTO so employees can't take PTO immediately; for example, you may have to wait 60 days or a year. There may be PTO or vacation and sick days, with sick days requiring that you actually be sick. Employers have recently been moving to PTO days rather than a combination of vacation days and sick days, which has sometimes come to the advantage or disadvantage of employees. It is often the case that the combined number of sick days and vacation days are greater than the number of PTO days given under new policies, but there is more flexibility in PTO days for healthy employees. Some states or cities may require that a certain amount of paid sick leave be given per year, so you may find that you have a combination of PTO and a minimal amount of sick leave as prescribed by law. It might be a good idea to look at work-from-home options if you are sick and you must work because of a lack of remaining PTO or a desire to not lose a vacation day.

One major concern with the change to PTO banks is that it encourages people to come to work sick rather than losing out on a day of vacation, which may be a good reason to work from home if you have the ability to do so. There are also issues with employees trying to use all their PTO near the end of the year so they don't leave any days on the table, in turn leaving the employer with far too few employees to cover the employer's needs near the end of the year. This makes it very important to make sure your days off are scheduled well in advance and thought through so your employer is not put in a bind.

How to Get the Most out of PTO

You can make your PTO days go further by strategically combining them with three-day weekends throughout the year rather than taking random weeks off. You may find that by combining your PTO days with three-day weekends, you can fit in an extra week of vacation or have a few spare days over the course of the year to either stay home or to use for sick days. Some employers will allow you to combine your leave with your PTO, whereas some will not.

## Flextime

Flextime allows employees to have flexible schedules where they can customize their work hours within a certain range of hours and days. Flextime can come in the form of compressed work weeks, flexible daily hours, or telecommuting, and it provides the flexibility to meet family needs, personal obligations, and responsibilities. Some options can save you money and stress, such as shaving time off your commute to work by shifting your commute from rush hours to times when traffic is not as heavy. It can help you avoid burnout, allow you to work when you feel the most productive, or give you control over your working environment if you work from home. It may also decrease childcare costs if parents can stagger their work times to reduce or eliminate childcare.

Requirements

Some employees who thrive in an office environment may be disadvantaged by people working flexible schedules or working remotely. To remedy this, some employers require employees to keep core days or hours so there are at least some days or times when everyone is in the office to coordinate and collaborate. For instance, an employer that requires core hours may require the employee to be in the office from noon until 3 pm everyday so the office benefits from coordinated efforts and people working together for at least a few hours out of the day while allowing employee flexibility.

It's also important for people who choose to work at home to make sure to check in and show progress to those who choose to go into the office; it can be easy for office colleagues to perceive that those working remotely aren't working if there aren't tangible outcomes from the remote work.

Flextime Options

Some employees may be given unlimited or limited ability to work from home or telecommute while working remotely since many jobs do not require a person to be in the office to be productive. Some employers may allow compressed work weeks, e.g., working longer hours four days out of the week and taking the fifth day off, working shorter hours four days a week and having one long day to make up for the difference, or working shorter hours six days a week.

Some employers allow employees to work from alternating locations; in other words, the employee may work from the office for four days a week and then work from home or a remote location on the fifth day. If used properly, any flextime arrangement can lead to a significant increase in quality of life and the ability to be more productive since you can take advantage of working on things when you are most creative and productive. You can also coordinate things in your personal life that need to be coordinated while helping prevent burnout. Make sure you stay active in communication and collaboration as much as possible if you are working under a flex arrangement so you are not seen as taking advantage of the benefit and as a productive member of the team.

## Work from Home

Some people work best in an office environment, while others work best and stay most productive working from home. So, it is important for you to know which camp you fall into before committing to working from home or the office. For the right people, working from home can increase productivity and decrease stress.

Benefits

For employees who work best in quiet, stable environments, working from home can reduce the amount of distractions faced because people do not come into their offices to disturb them while they are concentrating. At the same time, you cannot stop by a coworker's office to coordinate on an assignment as easily, so it's important to set up proper systems to collaborate while maintaining a distraction-free work environment. Working remotely may allow you to avoid office politics that you would otherwise be pulled into. Often, workers will need large chunks of uninterrupted time to really make progress on a project, which they can get through working remotely, but it's important to set up times during the day to check in on the people in the office and others working remotely. Introverts may find even more significant benefits from working from home because of the solitude it provides. Make sure to stay in touch with the office to not only keep up with changes in important information but also show you are working and engaged.

The lack of time spent commuting can save dozens of hours every week that can be put to better use in both your personal life and your work life if used appropriately. Some people use a combination of working from home and flextime to bifurcate their work day so they can wake up early, get started on work while they're most productive, take a midday nap or work out, and then come back to work having had some time away and some physical exercise so their minds are working at full capacity. Even something as simple as taking a walk around your neighborhood or through a local nature trail can be incredibly valuable over the course of the day since it provides a mental reset.

You may be able to save money by making your meals at home rather than eating out and by having more casual attire rather than the normal wardrobe expenses and trips to the dry cleaner. In addition, you may be able to work in a newer, more comfortable environment. Working remotely can also allow you to spend time with your family and pets that you otherwise might not have; things like working from an aging parent's home can be incredibly valuable to you now and in the future since that is time you can't get back, which may give you fond memories of your parent you might not otherwise get to have.

What to Be Aware Of

Make sure that if you work from home to decrease stress levels that you are not "always on" when you normally wouldn't be; otherwise, you risk compounding your stress and ending up burned out. It's too easy to let the desire to make sure people know you are doing well at your job while working remotely take over your personal life if there is no dividing line between work and home, which can cause you to overwork yourself so you're not seen as a slacker.

## Dependent Daycare Expenses

Your employer may have a dependent care assistance program, which could allow you to allocate up to $5,000 per year (unless you file married filing separately in which case you can allocate up to $2,500 per year) for child-care expenses pre-tax. This money can generally be used for a nanny or daycare.

Rules and Limitations

While these tax-benefited savings are generally used to take care of dependents while a legal guardian is at work, it can also be used for children of any age who are physically or mentally incapable of self-care or adult daycare for senior citizen dependents who live with you. The person for whose benefit the funds are spent must be claimed as a dependent on your federal tax return. The funds can't be used for summer camps, other than day camps, or for long-term care for parents living elsewhere. A dependent care FSA is federally limited to $5,000 per year per household.17 An FSA for dependent care is not fully funded at the beginning of the plan year by the employer, unlike medical FSAs. Unused amounts for dependent care also cannot be carried over, unlike some healthcare FSAs may allow.

The money allowed to be put in a dependent care FSA can be further limited if one of the spouses is not working and the non-earning spouse is not disabled or a full-time student.18 This can cause some very odd issues. For instance, if a single person elects to withhold the full $5,000 for childcare expenses and gets married to a non-working spouse before having filed claims for any of the money, the $5,000 would be forfeited because the newly married person can no longer take advantage of the dependent care FSA since the spouse is not employed; however, the $5,000 put into the plan would also be taxable. Thus, you would get no benefits and still have to pay taxes on the $5,000 you never received.

## Housing

Your employer may provide housing to employees; thus, it is important to know whether the housing is provided in a manner that will cause you to have to pay taxes so you are prepared at tax time. You may be exempt from paying all or part of the taxes on employer-provided housing if it's provided for the convenience of your employer, it's a temporary work location, or it's lodging furnished by an educational institution.

Liabilities

If you are provided with housing by your employer, you should ask for documentation containing a description of your responsibilities, a description of the lodging being furnished, the reasons why the lodging is required for you to perform your duties, a listing of taxable and non-taxable utilities, and services provided (such as phone, internet, housekeeping, and landscaping services). In addition, any events you have at the house connected with the business should be recorded in case of an audit. You should be very clear as to which utilities you will need to cover for the house. Furthermore, there are some very complex rules covering what is taxable and what is not, so make sure you understand what your tax liability will be after speaking to your CPA. If the employer owns or rents the home, it is also important to note who is allowed to occupy the property, if any pets are allowed, what rules are imposed on staying at the property, if smoking is allowed, if there are any quiet hours, if the employer can come in and inspect the property, any upkeep required for the property, and who is required to pay for utilities.

Potential Costs and Assistance

Housing assistance can come via specific dollar amounts for down-payment assistance or housing education programs and credit counseling. The employer may also provide closing-cost grants, deferred loans, mortgage guarantees, shared-appreciation mortgages, or donated or discounted land and buildings for development or redevelopment. Some states may also offer to match a certain amount of funds given to the employee by the employer for house down payments or closing costs. If you are staying in a home your employer owns or leases, make sure you know whether you are a tenant or under license. It may be easier for your employer to kick you out if you are under license if something happens at work and you are laid off, which creates a significant increase in insecurity.

## Student Loan Repayment

Optimal Use

Your employer may offer to make payments on your student loans. In such cases, it may be wise to think about not paying off any student loan amounts your employer might pay off for you if you plan on staying with the company so no money is left on the table. There may be a period that you have to wait before you start collecting contributions, such as working at the employer for one year before they start repaying loans, and there will likely be a cap (either per year or over the course of your career) on what they will repay on your behalf.

If you know you are taking a job with a company that offers student loan repayments after you graduate, it may be wise to think about taking on a certain amount of college debt even if you otherwise wouldn't have to in order not to leave money on the table.

General Considerations

Do not let student loan repayment be a driving factor in which job you accept because many benefits can add up to a more beneficial pay package over the course of your career. In other words, like every other benefit, it's wise to look at the combined benefits package rather than any benefit in isolation before choosing a job and negotiating for any missing benefits in the best benefit package offered to you before accepting a job. You want to look at the whole picture, including pay and the benefit package, rather than one benefit in particular, even if there is an emotional pull towards one benefit.

Special Considerations

  * Remember that any payments to you are currently considered income, so you'll have to pay taxes on the benefit.
  * Note that there is the potential to deduct student loan interest from your taxes while your employer pays your student loan off for you.
  * Some employers will offer to match student loan payments up to a certain amount with non-taxable contributions to retirement accounts rather than paying off the student loan directly, so you get a tax benefit from the employer benefit.
  * Some employers will offer monthly payments while others will offer lump sums, so it's important to understand the design of the plan.
  * Some will require you to have received your degree within a certain period before employment; for instance, you may have had to receive the degree within last two to three years to be eligible for student loan repayment.
  * Some employers will pay a certain amount per year with no cap, and some will make a certain payment amount per year with a lifetime cap.
  * Keep in mind that if you paid off your debt, you may not be able to get retroactive benefits for debt that no longer exist.
  * An employer may require you to refinance the student loan with a certain company. If they do, make sure the forgiveness terms, interest rate, and any loan servicing fees don't change the loan. Otherwise, be comfortable with how they will change the terms of the loan and consider converting only some of your student loans so you get the max employer benefit but keep the other preferable terms of your currently existing loan.

## Financial Advisor Fee Payment

The best form of this benefit is when the employer gives you a stipend to use to hire a financial advisor of your choosing. This ideal scenario is not universally used since your employer may also decide to contract with a single firm (which can create a false sense of security because you believe the information comes through or comes blessed by an employer). The employer may pay the upfront planning costs and depend on you to pay any ongoing costs, or they may pay a certain amount yearly for your benefit. This benefit can be provided on a one-on-one basis, through in-depth in-person workshops, or over the phone and computer consultations.

Potential Risks

Given what I do for a living, one would assume that I would be unabashedly for this benefit. However, it may come with strings attached that you need to be aware of. Sometimes, the person coming in to the company to give financial advice has volunteered to give the advice for free. This costs the employer nothing, and the advisor typically expects to make their money from commissions and other charges to the employee. A large red flag appears when you sit down with someone and within an hour, you end up with a recommendation to buy something that could affect the rest of your life. If that happens, you're likely talking to a salesperson and not an advisor. A skilled, experienced advisor working on a team of very competent people can take tens of hours to create and truly understand your financial plan and how everything fits together. So, even the best, most well-intentioned advisor can only do so much during a one-hour phone call.

It is important to learn from the advisor your employer may provide to you, but always remember that you shouldn't take for granted that the advisor has been vetted by the employer. It may be that the employer simply chose the person or company in charge of some of the company's other benefits. Similarly, even though your employer is paying for the financial planner to come in and talk to you, it doesn't mean that the advisor actually has your best interests in mind or that they won't try to sell you something to line their, or their firm's, pockets. This threat is ever present, making it important for you to make educated decisions about any options presented to you.

As with the college benefit, something that is free is not always without cost. This means bad advice, even if it's free, can be very expensive in the long run. It is important to be very careful to evaluate the person with whom you are speaking. You may be routed to an individual in a call center reading off a script who has little financial knowledge. A good way to make sure you are dealing with somebody who is at least minimally competent is to make sure they have the Certified Financial Planner® designation. This designation does not speak to how good somebody is at financial planning but simply shows that they are minimally competent at performing financial planning.

Key Considerations and Regulations

Other financial advice can typically be found in the 401(k) education provided by the employer; you should take advantage of this information. There is a general legal requirement that as a fiduciary, a 401(k) educator must have your best interests in mind, whereas a financial planner or advisor who is not acting as a fiduciary is not obligated to have your best interests in mind but instead the best interests of their firm. That said, when working with your 401(k) or any other financial matter, it is always to your benefit to use an advisor who is a fiduciary. It's important to have an ongoing engagement with the person who knows you and your financial plan due to the complexity and in-depth thought involved in financial planning. Oftentimes, an internet or call-in service is largely devoid of value outside very basic questions and financial education.

Some companies will pay you or give you health insurance premium discounts for participating in financial wellness activities or education, so it is always worth researching what is available to you.

## Relocation Assistance

Employer-provided relocation services may be provided as a lump sum or a direct reimbursement, or your company may provide paid moving services with a company with which they have contracted. The moving benefit generally covers the movement of household goods and people; it can sometimes include scouting trips so a new employee can visit the new location with their family and decide where they would like to live while they are beginning to assimilate to the new community. It may also include retention bonuses to employees if they stay with the new company or stay with the old company that's relocating them for a specific time frame. The employer may also provide trailing-spouse assistance for a spouse who stays behind while the employee sets up their new life in a new location. Housing benefits may come in the way of loss-on-sale benefits, quick-sale bonuses, and other incentives to help employees sell their homes and buy new homes.

Here is a general list of relocation expenses that may be reimbursable by your employer:

  * Travel
  * Hotels
  * Flights
  * Meals
  * Transportation costs
  * Household goods
  * Automobile relocation
  * Storage options
  * Miscellaneous cash allowances
  * Home search expenses
  * Real estate commissions
  * Temporary housing costs
  * Early lease cancellation
  * Home sale or purchase costs
  * Rental deposits
  * Home sale marketing
  * Physical move packing
  * Cost of turning off and on utilities
  * Cancelation fees to any clubs
  * Reinstatement fees to any clubs

*This list is by no means comprehensive. If you think that an expense might be reimbursable, ask your employer. It's better to ask and be told "no" than not to ask and find out later you left money on the table.

Potential Advantages

It is almost always a good idea to use any rental or temporary housing available to you in a new city so you can make sure you are comfortable living in the area of town you plan to live in. The ability to rent a place for a few weeks or a month while you keep everything in storage at your employer's expense and search for a place you are happy with is of substantial value, and you should utilize it if it all possible.

Potential Risks

Generally speaking, if the moving benefit is in the form of a lump sum or the reimbursement is given directly to you, it will likely have to be counted as income for tax purposes; this means you will have to deduct moving expenses from your taxes. If the money is paid directly to a third party, however, it may be excluded from work income. Make sure to work with your new company and your accountant to make sure you get the best after-tax benefit possible before beginning your move.

Key Considerations and Regulations

If a relocation package isn't brought up during salary negotiations, it's your responsibility to start the conversation; otherwise, you may not get an offer for relocation, especially if you have already signed a contract with the employer. Before negotiating, know what you'll need, including any special assistance for services; any special moving needs, including boats and paintings; and the sale and subsequent purchase of a house. You'll also want to know about how much your move will cost for each of the components so you have a baseline on which to negotiate. Make sure that when you are moving and you have a relocation package you know what it covers. Some may or may not cover packing or unpacking items; moving the car or second car; or moving exercise equipment, paintings, boats, and other items you may choose not to relocate given the personal cost to you if it's not covered under the relocation agreement. Make sure you keep track of all expenses and keep all receipts in case you must justify anything to the IRS or your employer.

It is important to know when to expect the reimbursement if you are being reimbursed for travel services or any of the other housing allowances. You don't want to depend on being reimbursed immediately and find out that reimbursement takes a number of years after vesting with the new employer before you receive any money. Following your move, your employer may provide relocation benefits in amounts paid incrementally rather than a lump sum.

It is always wise to get a quote from a moving company after they've seen everything in your current home since phone estimates are notoriously inaccurate. Make sure to walk through your house while recording a video of all your things on your phone so you have some documentation in case something is broken during the move. Finally, always make sure you deal with a licensed, bonded moving agency.

## Legal Plan

An employer may offer a group legal plan that provides access to a network of attorneys who have agreed to provide legal services at discounted rates. This may or may not be a benefit to you.

Here is a short list of different services lawyers may provide:

  * Informational and advice consultation;
  * Review and creation of legal documentation; and
  * Litigation and negotiation representation.

Potential Advantages

It is worth looking at the value of the plan, especially if you do not already have estate documents including your healthcare power of attorney, durable power of attorney, and will at the very minimum. These are essential documents in any financial plan, and the ability to obtain such documents at a discounted rate can be invaluable.

Potential Risks

It is always recommended to have an attorney draw up these documents rather than using online form templates to create your own. As is so often the case, we do not know what we do not know. Trying to draw up your own estate plan leads you into very deep waters that very talented people have made careers of understanding. The cost for estate documents can be high, but the consequences can be exponentially higher.

## Volunteer and Gift Matching

Volunteer and gift matching are excellent benefits that add value to employees, employers, and the community at large. With volunteer matching, your employer will usually donate money to an organization for which you volunteer for every hour you spend volunteering. With gift matching, your employer will match the money you donate to a cause you care about. For both of these benefits, your employer may set matching percentages up to a certain limit.

The types of volunteering work that qualify under volunteer matching can include all types of projects, from hands-on projects in the community to pro bono work in the area of your expertise. This can be personally rewarding for you and give you leadership experience, the chance to form connections with colleagues in your corporation, or the opportunity to mingle with people in varying industries outside the corporation. This leads to marketing for the firm and the ability to establish your personal brand.

Potential Benefits

Volunteering can provide a way for you to develop skills that are beneficial for your job and increase your value in the eyes of your employer. It also involves giving to a cause that you care about while your employer contributes to the same cause. This is a win–win for everyone involved: the cause, your employer, and you. Your employer gets a more well-rounded employee who gives back to the community in a meaningful way while potentially bringing in new business and garnering goodwill from the community that knows the employer is sponsoring the employee helping the cause. This brings about healthier communities that reap the rewards of employees and employers combining forces for the good of society.

Some companies not only match cash contributions but also contributions of securities to charitable organizations. This means there are additional benefits if you have highly appreciated stock you would like to donate to a charity. You get the tax benefit from gifting highly appreciated stock instead of cash, and there's a match benefit from the employer so that in after-tax terms, you give much less but the charity gets significantly more. You may also think about gifting directly from an IRA account if you are over 70.5 years old since such gifts can be counted toward your required minimum distribution; you not only get to give money to a charity and have your employer match it but also avoid paying taxes on the part of the required minimum distribution that went directly from the IRA to the charity.

Potential Risks

It is important to be cognizant of any conflicts of interest in using this benefit. In cases in which money is given to private foundations or donor-advised funds, gifts that provide benefits to you or your family (including advertisements) may be out of line with the intent of the program, leading to more than a few raised eyebrows within the organization. This type of conflict of interest may have consequences up to, and including, termination, possible civil or criminal liability, and a demand to return the matching gift amount from either the charity or from you, the employee.

Key Considerations and Regulations

To get the gift-matching benefit, an employee may be able to simply provide receipts; some cases may require a payroll deduction to have the company match dollars given. Some companies only match contributions to certain charities and limit the program to certain employees. This makes it very important to know how much can be paid out and the process for getting that amount paid out. You may need to keep documentation along the way or ask your HR department for approval of the charity before the gift is given. There is no reason to leave money on the table by not following the stipulations of the program, thus leaving the charity with less than they would have gotten if you had followed the program's rules. Gifts may have to be made during certain periods, and you may have to follow up with the organization you have given money to and confirm that the matching gift from your employer was made and received. It's also important to make the distinction that employer matching is not a deductible charitable contribution for the employee.

With respect to volunteer matching, an employee may need to show volunteer hours logged to get the company to provide gifts matching the hours volunteered.

## Tuition Reimbursement or Assistance

Your employer may pay for continuing education, part of your college tuition, or some tuition and college-related expenses for your family members. It's important to know what type of education your employer will pay for, and it's generally worth not leaving free money on the table when you can spend some of your employer's money to further your own education, either through college or continuing education courses. Some tuition reimbursement assistance programs will help pay for GEDs or language classes, while others require you to only take courses in your particular field or classes the employer deems useful for its purposes.

Potential Advantages

Some employers also choose to reimburse for expenses associated with higher education. These reimbursements can include books and an internet connection as long as one of your courses is online or has some internet component. This opens availability for someone who has an interest in learning, maybe about a specific course or subject they feel will increase their value in the job market, but who don't necessarily want to complete a degree program to gain the education they desire, and free internet or subsidized internet. In the right situation, you can actually make money by agreeing to take college courses that you get an A in because the value of the internet subsidy, and any other costs covered by the employer, are paid for while you increase your value as an employee. To extend the time during which you receive these additional education-related subsidies, it may make sense to think about taking one course at a time rather than several courses simultaneously if the employer will cover the full cost plus additional fringe benefits. This is recommended even if you aren't interested in furthering your education but are interested in having a certain number of subsidies from your employer.

Potential Risks

Some employers have teamed up with certain colleges, which can be a good or bad thing. The employer may have contracted, for a discount, with a for-profit school that is otherwise suffering for students and needs to attract the business. This could be troublesome since even after the discount, you may not get the value you are paying for. It is also important to consider that getting a discount on something worthless is far worse than paying for something that's worthwhile at full price. Think about the end goal of taking the courses: can you receive another degree through the college that will be of value, and if not, are the courses transferable? If the answer is no to both those questions, then it may be worth considering paying full price elsewhere to achieve your goals.

It is possible that all the discounts on college tuition you receive are a reduction from the university expenses and not actually a contribution from your employer. An employer may give a scholarship of a certain level of discount after factoring in any financial aid available. This means, you may use up some of your lifetime financial aid benefits by pursuing the employer-sponsored education plan, get a small discount on an education that is otherwise nearly worthless, and be unable to use the same benefits for the education you actually want. As stated earlier, a discount on something that is overpriced to begin with or that has no value is not a discount—it's a sales tactic.

Some of the discounted or free college education programs available to you might include online courses only. These can have value in terms of training you, but they may lack the value a normal college brings in terms of interactivity, such as getting to spend time with other people in your industry and growing your network, which can become a substantial asset over time.

There will almost always be an annual dollar cap on employer-provided educational assistance. In 2017, the IRS allowed your employer to reimburse you for or pay directly for any educational assistance up to a maximum of $5,250.19 Anything over that cap would be counted as income and taxed as ordinary income. This is an important distinction to keep in mind when it's time to file your tax return.

Key Considerations and Regulations

It's important to account for the cost of tuition and associated fees when deciding how to take advantage of this benefit since your employer may put a limit, either annually or per credit hour, on any courses taken.

Your employer may also require that you clear the specific course through HR so your program of study matches the employer's needs for you as an employee. You will likely be required to receive at least a certain grade point average in the courses you are reimbursed for, and you may find that there is a depreciating reimbursement depending on your grade (e.g., as being paid out at a higher rate than Cs and so on).

It's also important to know before taking a course when you will be reimbursed since your employer may not reimburse you until you have met a certain number of stipulations or certain vesting. You may also be required to provide proof of enrollment and your grade point average for all completed courses.

The amount of reimbursement you're eligible for may depend on the length of time you've been with the company, and there may be a cap on the number of classes you can take at a time or overall throughout your entire career. Keep in mind that some of these programs require you to remain with the company for a set period; otherwise, you may be required to pay your employer back for any tuition reimbursement received.

## Employee Assistance Programs

Employee assistance programs are meant to assist you with personal or work-related problems. They may offer confidential assessments, short-term counseling referrals, and follow-up services for those in your household. These programs generally provide short-term counseling and refer you to an outside resource. You may have only a few sessions or quite a number of sessions to take advantage of over the course of the year. The sessions can be either by phone or in person depending on your company.

Counseling sessions can be for any of the following issues:

  * Substance abuse
  * Occupational stress
  * Emotional distress
  * Major life events (accidents/death)
  * Healthcare concerns
  * Financial concerns
  * Legal concerns
  * Family issues
  * Personal relationship issues
  * Work concerns
  * Aging parent concerns
  * Marital trouble
  * Divorce conflicts
  * Depression
  * Weight loss
  * Mediation
  * Conflict resolution
  * Domestic violence
  * Workplace violence
  * Personal emergencies

*This list is by no means comprehensive. If you believe an issue is worthy of assistance, ask your HR representative for guidance and clarification.

There is a wide array of services offered by employee assistance programs and at your disposal. These benefits are generally also only given to family members covered by an employee's health insurance, but they may also cover other household members.

Potential Advantages

These programs are a great way to discuss grief and concerns regarding personal and workplace issues. They can help you with guidance and communication through difficult situations, such as mergers, layoffs, or when employees die on the job. In certain cases, employers may provide leave for victims of domestic or sexual violence. These programs may also work with management and supervisors to plan ahead for situations such as organizational changes, legal considerations, emergency planning in response to traumatic events, and support for disaster and emergency preparedness.

These programs can also help you find childcare resources and even resources for elder care assistance for parents and other family members. Some programs can find information about schools or colleges and connect you with nannies, childcare centers, and summer camps. Counselors can help find in-home caregivers, help navigate Medicare and Medicaid services, and provide support while you deal with emotional and other stressors associated with being a caregiver. You may also be able to ask them about the best assisted-living facilities or nursing homes in your area, and they may be able to make a call on your behalf to narrow the field of choices based on what you're looking for.

You can turn to financial counseling through these programs for ideas on budgeting, credit problems, foreclosure, bankruptcy, credit card debt, or any other financial issues that may bother you. They will in turn provide you with a base level of financial education and refer you to a good source for follow-up if necessary.

Employee assistance programs may also provide support for veterans' issues for people returning to the workplace as well as unique issues that may surface during a veteran's career both at work and home, including dealing with post-traumatic stress or readjusting to civilian life.

Key Considerations and Regulations

These programs are generally confidential; employers may request reports from the people who run these programs to see how much the service is being used and for what purpose, but they're only allowed to get aggregate information that doesn't identify any individuals using the service. However, when the counseling is mandatory due to disciplinary problems, the supervisor or HR representative may be told whether the employee is attending required sessions, and they may inquire about the employee's progress. Otherwise, these programs are usually run by a third party that is federally bound not to release any individual information about services used.

Keep in mind that the service may have certain hours of availability, although many have 24-hour hotlines so the systems can be used whenever you'd like. This way you can call from home so you're not worried about calling from a work phone.

## Adoption Assistance

Employer adoption assistance programs can provide information, financial assistance, and parental leave. Informational assistance can include:

  * Referral to licensed adoption agencies
  * Support groups
  * Access to adoption specialists

  * A specialist will walk you through the adoption process, answer any questions you may have, and help with special situations such as special-needs adoptions and non-domestic adoptions. These services can all be done either in person or over the phone.

Financial assistance can include a lump sum payment for an adoption fee and partial reimbursement to employees for expenses associated with the adoption. Financial assistance can cover costs related to the following:

  * Public agency fees
  * Private agency fees
  * Court costs
  * Legal adoption fees
  * Medical costs
  * Temporary foster care charges
  * Transportation costs
  * Pregnancy costs for birth mother
  * Counseling costs
  * Home study fees
  * Translation services
  * Travel and lodging
  * Immunization fees
  * Immigration fees
  * Lost wages for time taken off through the adoption phase

*This list is by no means comprehensive. If you believe an issue is worthy of assistance, ask your HR representative for guidance and clarification.

Potential Advantages

Employers may offer flexible time off and flexible work schedules for a set period after an adoption. A new adopted parent can generally take up to 12 weeks of unpaid leave after the adoption of a child, and it can be very wise to take advantage of this time with your new child to get them acclimated to their new home. The programs may also provide some employee education about adoption and post-adoption resources. These benefits can prove to be invaluable resources for you as new parents.

Potential Risks

You may find that the benefits paid to you for adoption assistance are taxable as ordinary income. This makes it extremely important to account for this additional income in any tax withholding that takes place over the course of the year and when filing your taxes at the end of the year. Make sure to speak with your CPA about how this assistance may affect your taxes as well as whether the adoption tax credit is available to you.

The employer may just provide a lump sum payment for the adoption rather than covering certain fees. You may also find employers that cover certain expenses or a certain percentage of expenses. In other situations, employers may only give a total dollar amount regardless of actual expenses.

Considering all these different scenarios available for adoption assistance, it's important to know beforehand what your employer will reimburse, what they will not reimburse, and the manner in which they go about covering the expenses. This also makes it important to keep track of everything, including receipts, as you work your way through the adoption process in case anything is called into question or is needed for tax purposes.

Key Considerations and Regulations

Your employer may require you to meet certain criteria, such as length of employment, full-time employment, or participation in the company-sponsored health plan to be eligible for the program. In some circumstances, the type of adoption can also affect the benefits (things like adopting a stepchild or an older child may not qualify you for adoption assistance, whereas adopting a child with special needs may give you enhanced assistance). In addition, remember that some employers may only pay for a single child adoption, whereas others may pay for you to adopt multiple children.

Your window to adopt may come across suddenly, and immediate action may be required. It's important to look at all the details of your employer-sponsored plan once you think about adopting and get everything lined up so you can act on a moment's notice.

Some qualified adoption assistance benefits may be excluded from the rules taxing fringe benefits. This makes it important to keep an itemized list of all expenses the company has reimbursed you for and those they have not reimbursed you for. This allows your CPA to take advantage of any and all exclusions to income that may be achievable through adoption benefits. Keep in mind that although these payments may be excluded from federal taxes, they may be included in Medicare, Social Security, or state taxes. The IRS may also cap the exclusion amount you're allowed to exclude from your income for any adoption assistance given to you by your employer per year, and it may also phase out the deductions allowed depending on your income; so that high-income individuals may not get the same tax benefits associated with adoption assistance programs as lower or middle-income individuals.20

## Family Caregiver, Maternal, and Paternal Leave

The Family and Medical Leave Act allows certain employees to take up to 12 weeks of unprotected, unpaid leave per year.21 This can be expanded upon by the state or the employer. The employer will continue to pay the employer-paid portion of your health premium (you may have to continue paying your portion of the premium during the leave). Upon returning from leave, you must be restored to the same job or an equivalent job. This means that, the leave does not guarantee that the actual job you held prior to going on leave will still be available and yours upon your return. However, you should get a job that is virtually identical in terms of pay, benefits, and other employment terms and conditions, including shift, location, and overtime. You should also be able to get any unconditional pay increases that occurred while you were on leave, such as cost-of-living increases.

The Family Medical Leave Act allows you to take time off at any time during your pregnancy or even after childbirth within one year of your child's birth. You may be able to take leave as a mother before and after having or adopting a baby, which is called maternity or pregnancy leave. Paternity leave for fathers is less common but is available at some firms.

If enough leave is not provided by your employer, you may be able to negotiate for more leave or negotiate to work from home or on a flex schedule to better suit your adjustment to life with a new child.

Potential Advantages

Some employers may allow you to continue working part or full time while technically on leave so that only days taken off to deal with acute issues qualify as leave. This provides the benefit of shortening the amount of leave time you need to take to deal with an issue and/or lengthening the amount of time over the course of the year you can stay on leave and still be considered an employee with benefits.

In certain cases, some states require employers to provide paid leave rather than just unpaid leave. Similarly, any loans taken from a retirement account may be allowed to have repayment suspended during the leave. Some employers will also provide community services, counseling, respite care, legal and financial assistance, and caregiver support groups for those on leave dealing with associated issues that would require those services.

After the birth of your child, a short-term disability insurance policy may cover part or all of your salary for a certain period. It's worth knowing what is covered in advance since some insurance companies may pay out for longer periods if you experience complications or have a C-section. Going on leave for a disability may also qualify you to begin pulling out any non-qualified deferred compensation money that has been put aside for your benefit to be paid at a later date.

Some states have short-term disability plans that pay for a certain period of maternity leave out of the office even if the employer does not carry any short-term disability insurance; so, it's important to know what is offered through the state for maternity or short-term disability leave. You may have to file within a certain period to take advantage of anything offered by your state in this regard. The state may cap the benefits at a certain level per person or at a percentage of your ordinary income.

Potential Risks

It's important to make sure you know whether your short or long-term disability policies will stay in place while you're on leave, especially if you may need to go on disability after the leave. If you find that going on leave may cancel your short or long-term disability policies, it may be worthwhile to debate going directly on disability rather than using leave. Short-term disability policies may also require you to use your sick time or vacation days before you start receiving payouts. Under these circumstances, you may strategically use your sick time and vacation days before the birth so your short-term disability policy kicks in sooner. The policies may also require you to be physically absent from your workplace for a certain period before receiving benefits.

Keep in mind that any decision to work part time before or after the birth may affect your ability to collect short-term disability payments. So, it is wise to know what your short-term policy covers (and under which conditions) before going to work part time or remotely for your employer during the time you take as maternity leave. It is also important to know whether you may have to pay back any of the short-term leave on maternity pay in the event that you do not return to work or quit within a certain period after returning to work.

Time spent on leave may or may not count towards vesting of benefits for defined benefit plans and may decrease the average pay you received over your years of service in pension benefit calculations. Deciding whether to take leave or retire (for in cases in which your final average pay may be lower if you take unpaid leave in one of your final years) may be necessary to make sure you receive the highest pension payment possible. You wouldn't want to decrease the pension payments for the rest of your life because you took leave for the last three months of your career, which makes any calculation of your last three years of pay much lower than it would have been.

Keep in mind that you may lose any bonuses, incentive pay, or equity-based pay during your leave of absence, typically depending on the type of pay and your role in the firm. Being out on maternity or other leave may affect things like raises, bonuses, seniority, participation in your company's 401(k) plan, vesting of the company's matching contributions, or stock options. In addition, you may not be able to contribute to your 401(k) or FSA while you're on leave.

Dependent care FSAs are not required to continue during leave, unlike standard FSAs. There may be a period during which you will have some coverage for dependent care but after which you will not be allowed to get any reimbursement for dependent care even if you put money into the account. This makes it very important to pre-plan this if possible.

Employers likewise keep FSAs in place during leave, but the coverage can lapse if you elect to cancel the coverage—during which time your employer is not required to make any reimbursements for expense claims. Even if you decide to discontinue coverage, the employer can keep the FSA coverage in place, and any amounts given to you during this period must be repaid by you whether you return to work after leave.

Some other potential risks to keep in mind include the following:

  * Sometimes, even an employee on leave can be laid off (e.g., due to downsizing or if the employee is a highly compensated employee who does not meet certain standards).
  * Employee assistance plans may or may not continue while on leave.
  * Any insurance acquired through work may or may not provide coverage for employees on leave. Make sure to inquire about the continuation of any life, health, dental, and vision plans and how you will continue to pay premiums for any available plans.
  * If the employer continues to pay your portion of insurance premiums during a leave period, you may be required to repay those sums after the leave has ended.

Key Considerations and Regulations

To be covered by federal regulations, you are required to work for your employer for at least one year and at least 1,250 hours over the previous 12 months (as long as the employer has at least 50 employees within 75 miles).22 You may be required to provide 30 days of advance notice when the leave is foreseeable. Under some circumstances, the employer may require you to use all PTO and sick leave as part of your unpaid leave.

Some other key considerations to keep in mind include the following:

  * Vacation may continue accruing while you are on leave, or you may be required to use all vacation days while you're on leave as part of the time you're away from the office.
  * Smaller employers and part-time employees are generally exempt from any leave policies required by the federal government; however, some may still be covered under state law, or the employer may opt to provide leave even though it is not legally required.
  * It's important to know how the health benefit coverage works while you're on leave so you can elect for money to be withheld to pay premiums from any checks you receive or prepay or write a check for coverage while you are gone.
  * Federal law does not cover the care of your father-in-law, mother-in-law, brother, sister, grandmother, grandfather, or adult child because "family" is defined a spouse, parent, or child under the age of 18, except relatives or other people who helped raise you or for a grown child who is severely disabled.

## Military Leave

An individual leaving on military leave may be entitled to pay increases they would have normally received had they stayed at the employer during the time of the leave, although there are some exceptions. They are also entitled to be reemployed in the same or a similar position and the same benefits upon returning to work (with some exceptions, including circumstances in which reemployment is impossible or unreasonable or in which reemployment would impose an undue hardship on the employer).

Potential Advantages

You are not required to use your vacation pay while on military leave like you may be required to for general leave. It may be worth thinking about using your vacation pay during the leave time to use optimal tax planning strategies and to provide additional income you may not otherwise realize if you do not return to your employer. For example, since pay while you're deployed isn't taxable, using your PTO first means you get paid tax free, and you can then take unpaid leave in another year to lower a second year's taxes. This strategy is better than having to pay taxes for your PTO days and being in a higher tax bracket than necessary the following year. Any time when you are deployed and not paying taxes on ordinary income may also be a prime time to convert some of your retirement plan money into Roth IRA money.

Keep in mind that leave provided by the government is unpaid leave, so the employer may choose to provide some pay during your absence. Under certain cases, if you perform work for the employer while you are on military leave, you must be paid your full salary from the employer minus any military pay. Unpaid leave is required in some amount for certain employees. However, some companies may opt to cover non-required employees during leave, have extended leave, or provide a combination of these two solutions.

While deployed, the military provides its own benefit of allowing you to put up to $10,000 into a savings account, giving you a guaranteed interest rate of around 10% during the deployment period. It is generally worthwhile to maximize your contributions to this plan.

As long as you continue your health coverage, the full amount of your FSA, minus any prior expenses for the year, must be available to you at all times during your leave period. However, if your coverage under the health plan terminates while you are on leave, you are no longer entitled to receive reimbursement for claims during the period in which the coverage was terminated.

Military members returning from military leave who have defined contribution retirement plans must be given three times the period of their leave of absence, as long as it's not greater than five years, to make up for any contributions missed during the leave period.23 This can be very beneficial in terms of allowing the military personnel to overcontribute to a deductible 401(k) plan, thus lowering their taxes for the years following the return from deployment.

It's worth keeping four other potential advantages in mind:

  * Your state may have greater protections than federal law, so it's important to look at not only federal law but also what your state has passed to protect you before going on military leave.
  * For pension purposes, returning service members must be treated as if they have been continuously employed for purposes of participation vesting in accrual of benefits.
  * You may be able to take leave to care for yourself or certain family members (e.g., parents, relatives, or even non-relatives depending on your employer).

Potential Risks

It is important to know which work benefits will be put on hold and what will stay in place. Don't assume that disability insurance, life insurance, or any other benefits will stay in place while you are on leave, whether you are receiving pay from the employer, working part time for the employer, or just on leave. It is important to talk to your HR department so you know in advance what benefits will stay and what will disappear while you are gone.

Generally, employers don't have to pay the cost of health insurance if you're on military leave unless you're on leave for less than 31 days. For longer leaves, you may have COBRA rights, which may require you to pay the full cost of your participation in your employer's health plan. If there are any lapses in paying any of the employer health insurance money due, you may find that even though your employer agreed to pay health insurance while you are on leave, your health insurance lapses and you are pushed onto a COBRA. So, it's very important to keep up with all necessary payments because you may need to write checks for the coverage since you are not receiving paychecks from your employer, which would otherwise withhold pay and send medical insurance premiums to the insurer.

If you have an FSA, you may find yourself in a position in which the Heroes Earnings Assistance and Relief Act (HEART) of 2008 (H.R. 6081) waives the "use it or lose it" clause of the FSA program. It's important to know whether you will need to spend down any of this money for any given period and what happens to this money if something happens to you during deployment so all contingencies can be planned for.

For dependent care reimbursement accounts, remember that you will have to maintain eligibility to use this money; otherwise, the money will no longer be available. For instance, if the spouse who is not deployed quits their job, the family may no longer be eligible for their dependent care reimbursement account.

Key Considerations and Regulations

Keep in mind that to get these military leave benefits, you must follow all applicable rules (including giving notice for the need to leave for military service). You must also be released from service under honorable conditions, and you must not exceed five years of military leave with any one employer (with some exceptions, such as annual training and monthly drills; these do not count against the cumulative total). The five-year limit does not include active duty training, annual training, involuntary recall to active duty, involuntary retention on active duty, voluntary or involuntary active duty in support of war, national emergencies, or certain operational missions.

There are also benefits for military caregivers. Military caregiver leave entitles an eligible employee who is the spouse, son, daughter, parent, or next of kin of a covered service member to take up to 26 work weeks of leave in a 12-month period to care for a covered service member with a serious injury or illness.24

It's important to note that you'll have to report back to your civilian job in a timely manner and submit a timely application for employment. This timeliness depends on how long you were deployed for, so it's important to keep track of all the rules and check off every box on your way back into civilian life.

Some other key considerations to keep in mind include the following:

  * Make sure you thoroughly read through anything your employer has you sign since you may be signing something that waives some of your legal entitlements.
  * You must report back to your civilian job by the appropriate deadline, which can range from eight hours to 90 days depending on the length of service.
  * Military leave coverage may vary for National Guard members performing state service rather than federal service for deployment.

## Discounts and Special Programs

Large employers often create an employee perk program with vendors, and possibly with other companies, to give employees discounts on everything from travel and cars to event tickets and physical goods. It's important to keep track of and know the criteria for the discounts you and your family can receive for goods and services from your employer and from other companies that have agreements with your employer. This can be a matter of using a special coupon code any time you go on to a certain website to buy a good or a service, downloading a form from the internet to order the good or service, or arranging for the purchase of the good or service through your HR department.

Your employer may also reimburse you for travel-related expenses or provide you with a company car; in such cases, free money should generally not be left on the table. If your employer does not provide for these expenses, they may still sponsor a qualified transportation plan that allows you to take up to $230 tax free per month out of your paycheck to pay for transit-related costs, including public transportation or even parking while at the office.

These discount and special programs have the potential to be extremely advantageous for employees. Knowing the benefits offered by your employer can lead to significant savings on things you would ordinarily spend money on.
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Acknowledgments

Harold Evensky, for teaching me to be analytical, thoughtful, and precise.

Deena Katz, for teaching me how to do more than I ever thought possible and molding me as a professional.

Ami Mungavin, for teaching me to give.

Danny Comilang, for teaching me how to be a calm in the storm.

Fred Smith, for teaching me how to be an ethical businessman and enjoy my work.

Bob Wishon, for teaching me what it really means to live well.

Lauren Harper, for teaching me how to provide support in times of need.

Anurag & Guddi for inspiring me to write this book
