Alan B. Ungar
NEW! The American Taxpayer Relief Act and the Affordable Care Act introduced tax-rate increases you need to consider in deciding when to exercise stock options, when to sell company stock, and how to plan around income from restricted stock vesting. This article explains the changes in tax law and suggests strategies for minimizing the new taxes.
Tom Davison and Liam Hurley
UPDATED FOR 2013! The time right after you have completed your tax return is ideal for big-picture financial planning. You can more accurately project your income and likely tax situation for the remainder of this year and the next, including AMT risk and capital-loss carry-forwards, to develop your strategy.
Tom Davison and Liam Hurley
UPDATED FOR 2013! Your tax return can help you develop your stock option strategy. With your return in hand, make projections for your income, taxes, AMT risk, and use of capital-loss carry-forwards. Next, review the details of your stock plan documents to develop an exercise program.
Tom Davison and William Whitaker
NEW! "My income is around half a million dollars, and I'm paying the alternative minimum tax. It's annoying, and I feel trapped. Now what?" Surprisingly, the best move may be to increase income, and pay even more alternative minimum tax! Find out why by reading this intriguing article.
Chris Murphy
Even when stock markets are depressed, there are still opportunities to achieve gains from stock compensation. This article presents a range of ideas to considerr: buying stock now to swap later, exercising and holding ISOs, or making a Section 83(b) election for restricted stock.
Timothy A. Farmer and Gregory G. Geisler
You can build your employee stock purchase plan into your long-range savings and retirement strategy. This article compares buying company stock at a discount through your ESPP to putting the same money into your 401(k) or another retirement plan.
Tom Davison
Your option grant terms and the behavior of your company's stock price are only part of your financial-planning story in volatile markets. Equally important is the price movement of what you will buy with the proceeds from an option exercise and stock sale. As this article explains, relative changes in price, not absolute changes, are what matter.
Sue Stevens
Weighing a Roth IRA conversion is complicated enough, but the complexity can explode when you add in stock option exercises or the vesting of restricted stock. Let's take a look at how this can work in real life through a case study.
Michael Beriss
When stock markets rise, question the urge to exercise your options for quick profits as soon as possible. Exercising too early can be a big mistake.
Stanley Trotta with Robert Gordon
With tax increases in mind, now may be a good time to re-evaluate your current financial-planning strategy for equity compensation and company stock holdings to determine whether action is required before new rates apply. Part 2 looks at restricted stock and restricted stock units.
Stanley Trotta with Robert Gordon
With tax increases in mind, now may be a good time to re-evaluate your current financial-planning strategy. Should you take action with stock options now or wait until new rates apply? Part 3 looks at incentive stock options.
Stanley Trotta with Robert Gordon
With tax increases in mind, now may be a good time to re-evaluate your current financial-planning strategy for equity compensation and company stock holdings to determine whether action is required before new rates apply. Part 1 looks at nonqualified stock options.
Tim Kochis
Once your stock options vest, you need a strategy to maximize their wealth-building value. But no single strategy fits everyone. This article discusses various approaches to planning your option exercises.
Tim Kochis
Part 1 looked at the basic exercise strategy for optionholders but underlined several exceptions to the rule. This article considers reasons and strategies for diversifying away from a concentrated position in your company's stock.
Alan B. Ungar
One of the most vexing investment decisions you will ever make involves when to exercise your stock options and when to sell the shares. This article series will give you the tools for determining that time.
Alan B. Ungar
Deciding which stock options to exercise and when can pose a dilemma. Part 2 of this series focuses on reducing risk when you exercise. Quantifying a risk/return number can determine the point when holding your options is no longer desirable.
Chris Murphy
If the majority of your net worth lies in unexercised stock options or company stock, it may make sense to sell a portion to reduce the concentration risk while holding on to a portion to participate in future appreciation. However, if most financial goals can be reached without these proceeds and your position is not heavily concentrated, other strategies are worth exploring. One that is gaining popularity is writing call options on vested ESOs to generate some income.
Carol Cantrell
Tax planning for retirees can be more challenging that it was during their working years. You need to constantly monitor any options and company stock holdings as part of your overall portfolio. Part 3 looks at special issues that can arise after you retire, including Social Security; coordinating with required minimum distributions for IRAs and your 401(k); moving to another state; and the gifting of stock.
Samuel D. Swisher
When should you exercise nonqualified stock options? You need a decision-making process that removes guesswork and emotions. Otherwise, you're likely to exercise too soon or too late.
Richard Friedman
Careful planning can help you maximize the value of restricted stock and RSUs by preparing you for decisions you must make. Part 2 covers complex issues in financial, estate, and retirement planning.
Tom Davison
Now that you understand the risks of choosing to be taxed at grant with a Section 83(b) election, should you do it? Part 3 takes you through the analysis.
Tom Davison
Vesting is another crucial time for making decisions about your restricted stock. Decisions include what tax-withholding method to use, whether you should hold or sell the stock, and what account to keep the shares or cash in after vesting.
Bruce Brumberg
myStockOptions.com
This PowerPoint presentation (in PDF) provides financial and wealth advisors with an overview of trends in equity compensation grants that can affect their clients and their practice. The focus is on the features and taxation of restricted stock grants and performance shares, and on the related financial planning. (Please allow up to a minute for the PDF to fully load in your browser.)
Russ Banham
Journal of Accountancy
Although stock options are no longer perceived as a quick path to riches, they still can be a powerful wealth-builder.
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For restricted stock, you can make what the tax code calls a Section 83(b) election to be taxed immediately at grant instead of later at vesting, when your stock price, and thus your tax rate, may be much higher. However, before you make your decision, realize that...
Before you even analyze the decision, you should learn the basic facts and risks of the Section 83(b) election. Once you understand it, the election can make sense in certain circumstances, including...
Let's look at the various tax permutations for nonqualified stock options (NQSOs)...
The outcome depends on how well your company's stock price does in the years after the grant date and on the ratio of stock options to restricted shares, among other factors. To calculate whether the appreciation of stock option gains equals or exceeds restricted stock gains, you need to...
Some type of periodic exercise-and-sell strategy can help even out stock-price volatility, spread out your tax bill, and eliminate...
The traditional strategy with NQSOs recommends waiting till...
Tax considerations alone should not drive the choice of what stock you sell. For example, if you are holding appreciated company stock from a nonqualified stock option (NQSO) exercise or restricted stock vesting, you will be taxed on...
By selling stock at a gain and then buying it back at the current price, you create a new...
A concentrated stock position occurs when a significant chunk of your net worth is tied up in a single stock. Strategies for hedging, diversification, and liquidity include...
Deferral means delaying the standard tax treatment that would normally occur when you receive income or undertake a specific transaction, such as...
A number of tax law provisions that may affect your stock grants were introduced in the American Jobs Creation Act (AJCA); the final regulations on deferred compensation under IRC Section 409A, which adopt the...
Estimated-tax periods end on the last days of March, May, August, and December, with payments due by the 15th (or the next business day) of the following month. If you are paying estimated taxes, one strategy is that just after the start of an estimated-tax period you can...
Experts suggest several strategies for you to consider when you exercise ISOs and are concerned about triggering the alternative minimum tax. For example, near year-end or at the beginning of the year, you can...
When you are intermittently subject to the AMT, tax advisors suggest different planning ideas on shifting income and deductions. You have much less flexibility in your planning when you project paying AMT for the next several tax years. A basic plan is to...
SEC Rule 10b5-1 provides a defense against charges of insider trading if you later trade stock while you know confidential, important information about your company. A Rule 10b5-1 trading plan is a program for the preset purchase and/or sale of your stock that meets the requirements of this SEC rule, including the need to...
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New Tax Act And Medicare Surtax: Impact On Stock Option And Restricted Stock Strategies 
