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Tax Planning Isn't Just For Year-End

Tax Planning Isn't Just For Year-End

| January 04, 2021
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It is tempting to try to guess what a new year and a new administration may bring and then speculate as part of a tax planning strategy. I encourage you to stick with the facts on the ground. The Executive Branch changed hands. In January, the Democrats gained control of the Senate, giving them control of three branches of the federal government. Even so, I don't think tax changes are likely to be the first thing on their agenda. Over the last two years, the Democratic majority in the House of Representatives has passed hundreds of bills to address climate change, racial inequality, police reform and voting rights. That stack of bills would be the first thing the Senate would want to review now that party power has changed. Over at the White House, the new President will probably be issuing a raft of executive orders to reverse and mitigate policies that were adopted by executive order in the previous administration. Again, these orders concern climate change, immigration law, tariffs and environmental protection. Changing the current tax law would require a comprehensive tax act. So, with everything a new administration and Congress will have on their to do list, regardless of the eventual outcome in each chamber, tax changes are unlikely to be addressed until at least 2022.

As for 2020, there is still time for tax planning before year end. Here are some things to consider for 2021

Tax Reform

The Tax Cut & Jobs Act (TCJA), which took effect back in 2018, was the biggest change to the US tax laws since 1987. These five categories of tax rules summarize the biggest impacts that continue to apply to people with earned income and equity compensation:

  • The top tax marginal bracket was lowered to 37% for single filers who, in 2021, have adjusted gross income (AGI) above $523,600 (above $628,300 for joint filers). Along with the rest of the rates, the statutory withholding rate for supplemental wage income, such as from stock compensation, has been lowered to 22% (the rate is 37% for amounts in excess of $1 million during the tax year).
  • Long-term capital gains (and qualified dividend) rates remain at 20% for high earners who have, in 2021, adjusted gross income (AGI) of more than $445,850 (more than $501,600 for joint filers).
  • The Medicare tax rate is still 1.45% for taxpayers with AGI up to $200,000 and 2.35% for single filers with AGI above $200,000 ($250,000 for joint filers).
  • The TCJA raised the standard deduction. For 2021, that standard deduction is inflation-adjusted to $25,100 for joint filers ($12,550 for single filers). If you are over age 65 or blind, you also receive an additional $1,350 deduction. The personal exemption has been eliminated. Several previously itemizable deductions have been eliminated or capped, meaning that many tax filers will no longer have enough deductions to make itemization possible.
  • The income exempted from the individual alternative minimum tax (AMT) will rise to $114,600 for joint filers ($73,600 for single taxpayers), so many fewer taxpayers will pay it.

Market Volatility: Opportunities and Risks

Thanks to a pandemic and a general election, 2020 turned out to be another volatile year for equities. 2021 may prove to be equally volatile. You should monitor your employee equity holdings throughout the year for the kind of tax-saving and portfolio-management opportunities that volatility can present.

Market-participants' experience over the last few decades may not be relevant to planning for the future or dealing with what has happened in the recent past. Market-behavior assumptions, developed during the post-1945 economic expansion of the US and based on research, opinion, and empirical experience, is proving in many cases to be inadequate for explaining what happened or what may be the best choice of action in the continuing slow-motion recovery we experienced between 2010 and 2019. Even though the pace of recovery accelerated, as evidenced by record low unemployment and modestly rising wages, the Federal Reserve's interest-rate policies made it seem that it was concerned that the economy would experience slow going into 2020 and beyond. Then the pandemic hit and Fed policy was back to focusing on historically low interest rates while Congress has flooded the economy with trillions of relief dollars. Given the fall and winter spike in Covid-19 cases, it’s reasonable to assume that Congress will be under increased pressure to enact some sort of additional economic relief either in the lame duck session or after the inauguration. There is little agreement, however, as to what effect additional stimulus will have on already-strained and extended financial markets.

More than ten years have elapsed since the 2008–2009 credit crunch and market crash. Don't be fooled into believing that the recovery from historically volatile lows to where we are now is a pattern that will be perpetuated, indefinitely. We experienced the longest post WWII recovery ever. Markets were showing signs of slowing down in the last two quarters of 2019. Then we struggled through a year during which markets tried to make sense of a global pandemic that disrupted demand and interrupted supply chains. Many advisors tell investors to pay more attention to long-term market trends than to short-term shocks. But today it may not be prudent to rely on the 50 years of financial-planning and market behavior assumptions, based on data from the post-oil-embargo 1970s through the beginning of the 21st century because it may not provide relevant guidance for this environment.

Like it or not, we live in a slow growth, low interest rate world where we should logically have simultaneously lower return expectations and, thanks to medical advancements, longer life spans, I think it is more important than ever to adhere to conservative principles of tax management and portfolio balance that we know make common sense in any market. We discuss these below.

NQSOs And Restricted Stock: Little You Can Do

The spread between the exercise price and the market price of nonqualified stock options (NQSOs) is taxed as ordinary income at exercise (as is the value of restricted stock at vesting), and the tax is fixed on that date. If you know your tax bracket will be higher this year, because an exercise will push your marginal income into the highest rate, you may want to consider straddling years for your NQSO exercise to take the compensation income in the lower-tax year, going just up to the 37% threshold but not over it.

With restricted stock or restricted stock units, you usually have no flexibility in choosing the tax year, as the vesting date is set, but you may be able to defer the tax consequence by designating the vesting to a deferred compensation plan. Beware of building up a concentration of company stock in your deferred comp plan, though. Market drops can cost as much or more than tax bills. 

With NQSOs, unlike with ISOs, nothing at year-end can change the tax impact of your exercise earlier in the year, regardless of whether your company's stock price has dropped (or risen) since you exercised. After you exercise and hold NQSO stock, the holding period begins, and it is simply stock with no special tax status. Evaluate it like any other investment (a similar analysis applies to restricted stock after it vests). When you sell the shares, the rules of capital gains tax apply.

Maxed Out On Social Security?

For NQSO-holders who max-out their Social Security tax at that point during 2021 when they earn over $142,800, any additional exercises before the end of the year will occur without Social Security withholding, letting you keep an additional 6.2% of the spread. Remember that, as stated above, the Medicare tax is 2.35% for single taxpayers earning over $200,000 ($250,000 for married joint filers), and a Medicare surtax of 3.8% on investment income also applies to those same taxpayers.

Taxes Should Not Drive Decisions

Remember to never base any decisions solely on taxes or expected future tax rates. If in December you sell at $20, merely to "take advantage" of your loss for stock exercised at $30 per share earlier in March, you lose the opportunity for future appreciation in the stock. Should it double to $40 by the following June, you will miss out on a gain of $20 per share. This is one reason why you should almost never make exercise or sale decisions based solely on tax considerations.

You should always base exercise and stock-sale decisions on a determination that your company stock has peaked, on a need for money, or on a desire to seek diversification. You may come to these conclusions by a number of paths but "buy low, sell high" is still the only way to make money in the market. Yes, your profits will be taxed, but you'll never build wealth by taking losses! You may reduce your income taxes with a year-end sale, but you eliminate your real opportunity to make money over the long run.

Be Sure You Can Pay Your Taxes

Always double-check that you will have the money to pay your taxes. You may owe some income tax beyond what your company withheld at exercise or at vesting with restricted stock/RSUs. When you exercise NQSOs or when your restricted stock/RSU grants vest, your company withholds federal, state, and Social Security taxes.

Potential Withholding Shortfall

Most companies withhold federal tax at only the minimum required federal supplemental income withholding flat rate of 22% (37% for total yearly amounts of supplemental income in excess of $1 million). If you are in a higher tax bracket, you may owe the additional amount with your tax return (or through estimated taxes), unless you're fortunate enough to have made more than $1 million in supplemental income.

For nonemployees (e.g. consultants or contractors), the company might not have withheld taxes at all, in which case you should expect to receive an IRS Form 1099-MISC that reports the income. Ask your accountant or financial advisor to estimate your tax liability and then make sure you can cover it. This may mean you will need to pay estimated taxes and/or sell more stock this year, but at least you will be confident of your ability to pay taxes.

Sell Losers

Despite the long market recovery, because of volatility you may still have some shares whose prices are significantly below what you paid for them. Consider selling stocks that have lost value, but only when you expect the stock to continue to lose value. The best reason to sell a stock is that it's no longer a good investment. You may even want to sell the stock if you think it is not going to appreciate as quickly as alternative investments. If you expect only a small recovery in your stock but believe the market is going to appreciate substantially, sell, harvest the losses, and purchase something else.

Know the Rules On Loss Deductions

Consider stock sales that generate losses to deduct. If stock acquired from an option exercise or restricted stock/RSU vesting is now worth $5,000 less, the sale will generate a $5,000 capital loss. This may reduce your tax liability, but whether the deduction is immediately usable depends on the rest of your tax situation, including the gains and losses from other stock sales and loss carryforwards from prior years.

The new tax law didn't change capital gains rules. You can offset losses only against the same type of income. This means you cannot use a $5,000 capital loss to offset $5,000 of your salary. However, you can use the $5,000 capital loss to offset a $5,000 capital gain.

There is one small exception to the "matching" rule. You can use up to $3,000 of capital loss to offset $3,000 of ordinary income, carrying forward any unused losses to next year. Therefore, if you sell only enough stock to generate $3,000 of capital loss, you will most likely get a deduction for the full amount. If it turns out that your tax rates are eventually higher in 2020 and beyond, consider one "benefit" you may not have thought about: higher rates make loss carryforwards more valuable to offset against ordinary income. Current tax rules allow write-offs against ordinary income up to $3,000. In the top 37% bracket, the offset will be worth $1,110.

If you think your company's stock is overvalued or you are overconcentrated in it, consider taking capital gains by year-end to use up losses from this year or losses carried forward from prior years. You should pay close attention, as we approach year-end, for an opportunity to sell at a loss those appreciated shares along with an offsetting number of shares from previous vesting and exercises. This will help you diversify, raise cash, and position yourself for what may come.

Sell If You Need Money

Even with the tax changes, your stock gain at sale is taxed at the long-term capital gains rate of only 15% or 20% (depending on your adjusted gross income) when you have held the shares for more than one year. Capital gains are still preferable to ordinary income.

Should you need money to pay for your child's college tuition in January, sell stock. Always keep your short-term cash needs out of stocks so that you can ride through any short- or long-term drops in the market. While we're on the subject of college tuition, the American Opportunity higher-education credit, which offers up to $2,500 annually per student for four years of college and covers tuition, room, board, and books, was kept unchanged in the new tax law. The credit begins to phase out at $80,000 of AGI ($160,000 for joint filers). If the credit is more than your income-tax liability, 40% of it is refundable. Also, the full credit is allowed against the AMT. For more on the use of company stock to pay for education.

Consider Gifting Stock to Relatives in Low Tax Brackets

You may make annual gifts of $15,000 ($30,000 if you split the gift with a spouse) to any number of recipients without either affecting any portion of your lifetime gift tax exemption or paying gift tax. Financial planners often advise high-net-worth clients with substantial estates to consider making annual stock gifts before the end of the year, up to these amounts. Depending on the size of your estate at death, a strategy for making lifetime gifts can reduce your estate taxes, particularly if the value of the shares rises significantly after the gift. High-net-worth individuals should consider a grantor-retained annuity trust for their company stock.

The long-term capital gains tax rate on people in the 12% tax bracket is 0%. If you have adult children, who file their own tax returns and whose income is likely to be in the 12% tax bracket in 2021, they will pay 0% tax on long-term capital gains that don't cause their income to rise to the next bracket. Consider a gift of appreciated shares to them up to the annual gift limit before year-end.

Alert: The kiddie tax (i.e. your tax rates, not your children's) will apply to stock sales by your children under the age of 19 as well as college students under 24 unless the students provide over half of their own financial support from earned income.

Retirement Planning: It's Not Too Soon

Equity compensation exercise strategies should, ideally, be coordinated with your retirement planning (to hear my thoughts on how best to do this, listen to my podcast Retirement Planning With Stock Compensation). It's not too soon to plan for future years or too late to make a retirement plan contribution for the previous year. Even if you are covered by a retirement plan, such as a 401(k), at work, you can take a full IRA deduction for 2020 if your modified AGI is less than $66,000 ($105,000 for married joint filers). A partial deduction is allowed until your AGI reaches $76,000 ($125,000 for married joint filers).

For the 2021 tax year, the contribution limits for a Roth IRA are $6,000 for a person under 50, and $7,000 for a person who is 50 or older before the end of the year. To be eligible for maximum contributions in 2021, married joint filers must have MAGI of $198,000 or less, and single filers must have MAGI of $125,000 or less. The phaseout range for partial contributions extends from there up to an income ceiling of $207,999 for married joint filers and up to $139,999 for single filers. Beyond that point, contributions are not allowed.

Alert: Up to the filing deadline of your 2020 tax return in April 2021, you can make contributions that still count for the 2020 tax year. (IRS Publication 590-A has more information.)

If you are already contributing the maximum to your 401(k) at work or if you have additional compensation income this year from your stock option exercise or restricted stock/RSU vesting, making you ineligible to fund a Roth IRA or deductible IRA, you may want to consider funding a nondeductible IRA with the expectation that it can be converted to a Roth later. When you do convert your traditional IRA to a Roth IRA, you will owe ordinary income tax on the value of any tax-deductible IRA (speak with your tax advisor about the related calculation). Income from your stock compensation can help you pay this additional tax.

Year-End Planning For ISOs

Year-end planning is especially important for anyone who has exercised incentive stock options (ISOs) during the year. Unlike nonqualified stock options (NQSOs), ISOs are quite often exercised with the intention of holding the stock to qualify it for long-term capital gains treatment on the full gain over the exercise price. The most likely recipients of ISOs in today's market are employees of companies that went through an IPO this year or last, as this activity has dramatically ramped up over the past few years (see my blog post about financial planning at IPO companies).

Other employees may be holding ISO stock because of the opportunity presented by a dramatic drop in stock prices at some point in the last several volatile years. Alert employees may have jumped at the chance to exercise ISO grants that were made when the company's stock price was abnormally low (see my article about Managing Market Volatility).

This year's volatility may have you thinking that a market top has been reached. On the other hand, if your confidence about your company's outlook has risen, you may be thinking about exercising and holding now. Or, maybe the market's performance over the past few years has caused you to consider locking in your gains on options you exercised more than a year ago. No matter your rationale, below are some things you should think about if you have ISOs or have exercised ISOs in the past.

Determine Your Alternative Minimum Tax (AMT) Opportunity

Under the Tax Cut and Jobs Act (TCJA), the alternative minimum tax (AMT) calculation dramatically changed. While the AMT didn't go away, the rules are now a bit more friendly to taxpayers than they were before 2018.

Impact Of Tax Reform On AMT

For both single and joint filers, the 26% AMT rate rises to 28% when AMT income in 2021 exceeds $199,900 ($99,950 for those who are married but filing separately). The TCJA also increased the exemption amounts and phaseout thresholds that you are allowed to subtract when calculating your AMT income. The exemption is phased out when your AMT income surpasses the applicable threshold. For 2021, the exemptions are $114,600 for married joint-filing couples and $73,600 for single filers. The phaseout starts at $1,047,200 for joint filers and $523,600 for single filers. The AMT exemption is reduced by 25% of the excess of AMT income over the applicable phaseout threshold. So, under the current tax rules, only truly high-income folks see their exemptions phased out, while middle-income taxpayers benefit from full exemptions.

AMT Credit

The enlarged AMT exemption and higher exemption phaseouts will benefit people who had to pay the AMT in prior years. These taxpayers generated a minimum tax credit (MTC) when they exercised ISOs and held the associated stock with the expectation that they would get long-term capital gains tax treatment on the full appreciation when they eventually sold. It turns out that some of these people couldn't ever use their MTC. They continued to be subject to the AMT, year after year, because of high income, big deductions and/or additional ISO exercises. Now they will probably be able to use up most of their MTC because of the higher AMT exemption and phaseout point. A much larger gap between the household's regular tax and AMT lets them claim their credit carryforwards. It is unclear whether Congress really intended to give these taxpayers big AMT relief, but it could be an unexpected Christmas bonus for some highly compensated executives.

Calculate AMT Cushion

No matter what the rate or level of exemption is, the AMT may present an opportunity. If you have not already exercised any ISOs this year, ask your accountant to determine your AMT spread. This spread is the difference between your ordinary tax and your AMT obligation. Even though itemized deductions have been reduced under the new tax law, the spread at ISO exercise can be large enough to trigger the AMT. If you calculate that your 2021 ordinary tax is greater than your AMT, you have an opportunity to exercise some more ISOs without owing any additional tax.

Example: Your accountant says that your ordinary tax is $70,000 and your AMT is $60,000, meaning you have a $10,000 AMT spread. You can generate an additional $10,000 of AMT without paying any extra taxes. Assuming you are in the 28% AMT bracket, you may be able to exercise ISOs with a spread of $35,714 without paying any additional tax (this generates $9,999 of AMT). The exercise begins your holding period to qualify for long-term capital gains. As a result, you will be able to sell the stock after one year from exercise (two years from grant) and pay only the lower long-term capital gains tax on the full increase over your exercise price.

This may not be to your advantage if you currently have an AMT credit carryforward from a previous year. (Of course, you should confirm any tax calculations with your accountant and other advisors.) However, the AMT spread sometimes provides an opportunity to generate income without generating additional tax.

Decide About ISO Stock That Has Lost Value Since Exercise

As the year develops, pay attention. Not every stock will higher than it was earlier in the year. If you exercise and hold ISOs this year and the stock drops in value after you  exercise, you have to make an important decision. Should you sell the stock before the end of the year of exercise to eliminate the AMT, or should you simply sit still and hope the stock price will recover?

Example: You have an exercise price of $10. You exercised your option on January 15 of this year, when the stock had a value of $50. You generated $40 per share of alternative minimum taxable income (AMTI). If you are in the 28% AMT bracket, you will owe $11.20 per share of AMT (with an AMT credit to use in future years). You plan to hold the stock until January 16 of the next year. You intend to sell the stock and pay only long-term capital gains on the profit.

However, on December 1 the stock is trading at only $20 per share. If you sell the stock, your tax calculation changes substantially: selling the stock is a disqualifying disposition, and the gain is taxed as ordinary income. The gain, though, is limited to the difference between your exercise price ($10) and sale price ($20). You will have only $10 per share of ordinary income. If you are in the 37% top federal tax bracket you will owe $3.70 per share. The original AMT is simply eliminated.

You must make a decision. If you sell in December, you will have to pay only $3.70 of tax. If you wait until January of the following year, you will have to pay the AMT of $11.20. You will get a credit for some of the AMT, but it may not be easily usable. Therefore, you may want to sell in December to eliminate the AMT liability.

Of course, the numbers all change for the better if you do not sell in December and the stock recovers to $50 per share in the following year. Although you will still owe the $11.20 of AMT, you will make a lot more money by selling at $50 instead of at $20 per share. In this situation, you should consider selling if you are concerned that the stock price may not appreciate, or if you do not have the funds to pay the AMT. If you have the money to pay the AMT and expect the stock to appreciate, waiting to sell may still be worth considering

Evaluate Your Own ISO Situation

It's important to determine:

  • your AMT liability without a sale
  • your ordinary tax liability if you sell
  • how you will pay your AMT if you don't sell

In addition, remember to factor in your confidence in the future value of your stock. If you think the stock is going to appreciate substantially, waiting is your best choice. Exercising ISOs early in the year to start the 12-month holding period gives you more time to watch the stock so that you can decide whether a disqualifying disposition is prudent.

Consider Year-End Gifts Of Appreciated ISO Stock

Some tax strategies come into more focus as the end of the year approaches. The long-term capital gains tax rate on people in the 12% tax bracket is 0%. You may have adult children, retired parents, or other lower-income family members who file their own tax returns and whose income is likely to be in the 12% tax bracket. If so, they will pay the 0% tax rate on any long-term capital gains that don't raise their income to the next bracket. Consider giving these family members a gift of appreciated shares before year-end up to the annual gift limit ($15,000 per person, per gift). Gifting highly appreciated ISO shares can also be a wise way to remove value from your taxable estate, though you should be aware of the kiddie tax rules and the caution about gifting ISO stock discussed below.

Beware Of Gifting ISO Stock Too Early

Don't get carried away by the holiday spirit! Gifting stock that is generated from the exercise of an ISO is considered a disposition. If you have not met the required holding periods and you gift the stock, the gain at exercise is taxed as ordinary income in what is called a disqualifying disposition. This includes gifts to charities, family members, or others. Therefore, you may not want to gift the stock until you have met the ISO holding periods. Other planning issues arise if you triggered the alternative minimum tax when you exercised ISOs to acquire the shares that you later gifted.

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