Your Stock Award

How Your Stock Award Is Taxed

Rande Spiegelman

With a restricted stock award, the time period for determining your eligibility for long-term capital gains tax treatment starts on the day that the restrictions lapse. Restricted stock awards let you take advantage of a so-called "83(b) election," which allows you to report the stock award as ordinary income in the year it's granted and then start the capital gain holding period at that time (caution: if the stock fails to appreciate, you don’t get a refund of the tax you paid when you made your election). Your alternative is to defer paying any tax until the stock is fully vested – but at that point, you'll be paying ordinary income tax (up to 35% through 2012, depending on your tax bracket) on what could be an appreciably higher number.

Restricted stock units, unlike restricted stock awards, aren't eligible for an 83(b) election because no stock is actually issued to you when the units are granted (and you can't pay tax on a thing you don't own yet). What you're getting is essentially a promise that on a date in the future, you'll be issued the stock if you've met all the vesting requirements. On that date, you will pay ordinary income tax on the value of the stock. After you've been issued the stock and you sell your shares, you'll either incur a capital gain or a capital loss (cost basis equal to the value of the shares at vesting), which will be treated like any other stock sale.

Stock Options

With stock options, taxes come into play at the time you exercise your options.

Incentive stock options (ISOs) receive special tax treatment as long as you meet certain conditions.

IF: You sell your shares more than two years from the grant date AND more than one year from the exercise date

THEN: The spread—the difference between the strike price and the market price on the date of exercise—is exempt from ordinary income tax. When you sell the shares, any gain is subject to the favorable long-term capital gains tax rate.

CAVEAT: Exercising ISOs may trigger alternative minimum tax (AMT), so check with your tax advisor before you exercise ISOs.

IF: You sell your ISO shares without meeting the holding period requirements—what's called a disqualifying disposition—and if the sale occurs in the same year as exercise

THEN: The spread and any gain from the sale of the shares are taxed as ordinary income.

Nonqualified stock options (NQSOs) are taxed differently. The spread—the difference between the strike price and the market price on the date of exercise—is taxed as ordinary income in the year of exercise and is subject to income and payroll tax withholding.

IF: You hold the shares more than one year after you exercise and sell the shares for a gain

THEN: The subsequent gain is taxed at the long-term capital gains rate (cost basis equal to the share price value at the time of exercise).

IF: You hold the shares one year or less after exercise and sell for a gain

THEN: The gain is taxed at your ordinary income tax rate.

Strategies for Reducing Your Tax Burden

As with most things tax-related, you should consult with a tax advisor who's familiar with your state's rules and your particular financial circumstances. The right strategy for you will depend on many things, including how your company has structured your stock award and what type of award you've been granted. That said, here are some of the more common strategies for reducing compensation-related taxes:

Consider maxing out your 401(k). You can contribute up to $17,000 per year into your 401(k) plan—or up to $22,500 if you're 50 or over. 401(k) contributions aren't taxed until withdrawal, so you're not only deferring taxes on your contributions, they're also growing tax-free.

Determine if an 83(b) election is an option for you. If you're granted a restricted stock award, you have two choices: you can pay ordinary income tax on the award when it's granted and pay long-term capital gains taxes on the gain when you sell, or you can pay ordinary income tax on the whole amount when it vests. Here's an example:

You're granted 10,000 shares of restricted stock on January 1, 2013. At that time, the stock is worth $20 per share. Five years later, when the stock vests, it's worth $30 per share.

If you take the 83(b) election, you lock in the income tax and long-term capital gains tax rate that's in effect when you make the election. You'll owe the IRS ordinary income tax on an extra $200,000 worth of income in 2013—at a 35% tax bracket, that's $70,000. Then, if you sell as soon as you vest, you'll owe long-term capital gains taxes on the profit you make—in this example, $15,000 (0.15 x $100,000). Total tax paid: $80,000.

If you don't take the 83(b) election, you'll owe ordinary income tax on the whole amount (0.35 x $300,000). Total tax paid: $105,000.

So why not take an 83(b) election? First, you could lose your job before the stock vests. In that case, you'd never own the stock outright, and you can't reclaim the taxes you already paid on it. Second, the stock price could fall between the grant date and the vesting date, which means the ordinary income tax you paid on the grant date would be higher than the ordinary income tax you would have paid on the vesting date if you'd waited. An 83(b) election might make sense in a pre-IPO scenario when the share price is extremely low, but could be a big gamble for post-IPO shares with a higher price tag. The 83(b) election is irrevocable with no relief for taxes paid, so be sure to consult your tax and investment advisors before making a decision either way.

Consider donating to charity. There are a couple alternatives here:

Donating appreciated stock directly. You can gift appreciated long-term positions to qualified charities for a full, fair-market-value tax deduction (subject to adjusted gross income limitations) and no capital gains tax.

Donating stock to a donor-advised fund. When you contribute to a donor-advised fund you open and fund your account with an irrevocable, tax-deductible contribution—but you don't have to decide right away how you want to give. Your account has the potential to grow tax-free, and when you're ready, you can recommend grants to the charities of your choice.

Donating stock to a charitable remainder trust (CRT). A CRT can give you an immediate tax deduction for the value of your gift or generate annual income for a set number of years. At the end of that time, the remaining assets to go charity. The gain on any stock sales, along with any potential ongoing current income or appreciation on the trust portfolio, is taxed only when funds are withdrawn from the trust, typically on an annual basis over a period of years.

Read more:

Stock options and taxes >
How to find a financial advisor
Giving to charity>