Tax Center / Global Tax Guide / Glossary / Discussion / Newsletters / About Us
Register Log in
myRecordsmyToolsmyClients
   Financial Planning   
Strategies   
Advanced Strategies   
Diversification   
High Net Worth   
Estate Planning   
Gifts   
Dividends   
Year-End Planning   

QuizzesCFP® Credit
Earn up to 15 continuing education credits when you pass our exams for financial planners

Annotated diagram of Schedule DTax errors can be costly! Don't draw unwanted attention from the IRS. Our Tax Center explains and illustrates the tax rules for sales of company stock, W-2s, withholding, estimated taxes, AMT, and more.


Financial Planning: Year-End Planning


Test Your Knowledge Test your knowledge with our Financial Planning quiz.

Visit our podcasts page for interviews with some of our expert contributing authors on financial planning.


  Articles   FAQs  

Top Ideas For Year-End Tax Planning With Stock Compensation (Part 1)

The myStockOptions.com Editorial Team & Contributors
UPDATES! Understand the core concepts in year-end or year-beginning tax planning for stock options, restricted stock/RSUs, and company stock. Recent changes in tax law continue to have significant impacts on year-end planning, and this article presents some ideas to consider.

Top Ideas For Year-End Tax Planning With Stock Compensation (Part 2) This is premium content

The myStockOptions.com Editorial Team & Contributors
UPDATES! Understand the core concepts in year-end or year-beginning tax planning for stock options, restricted stock/RSUs, and company stock. Topics in Part 2 include the alternative minimum tax, donations and gifts of stock, and capital gains strategies.

Year-End Strategies For Restricted Stock, RSUs, And Performance Shares: Seven Ideas To Consider This is premium content

Bruce Brumberg
UPDATES! As part of your year-end and year-beginning tax planning, don't forget to review your holdings in restricted stock, restricted stock units (RSUs), and performance shares. This article presents strategies that many experts suggest.

Year-End Strategies For Employee Stock Purchase Plans: Ideas To Consider This is premium content

Matt Simon
UPDATES! When you think about year-end financial and tax planning, don't forget to review shares acquired through an employee stock purchase plan. This article outlines issues and strategies to contemplate.

Stockbrokers' Secrets: Year-End Planning For NQSOs, Restricted Stock, And RSUs This is premium content

W.E.B. Bantling and Michael Beriss
UPDATES! Learn about year-end ideas that apply to NQSOs and restricted stock/RSUs, and consider the impact of recent tax-rate changes.

Stockbrokers' Secrets: Year-End Planning For ISOs This is premium content

W.E.B. Bantling and Michael Beriss
UPDATES! Learn about year-end planning for incentive stock options. This article includes ideas related to the alternative minimum tax.

Restricted Stock & Stock Options: Financial Planning After Your Tax Return Is Filed And At Year-End (Part 1) This is premium content

Tom Davison and Liam Hurley
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.

How Tax Rate Changes Impact Your Stock Grant Strategies (Part 1): Nonqualified Stock Options This is premium content

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. Part 1 looks at nonqualified stock options.

The ISO Tax Trap And The AMT Credit Myth: What To Do Before Exercise And At Year-End This is premium content

Alan Ungar
The tax reductions of the past few years have brought both good and bad news for holders of incentive stock options. While you may have lower capital gains rates when you hold the shares long enough after exercise, it is harder to avoid the risks of the alternative minimum tax (AMT) and to fully recover any AMT credit.

Year-End Tax And Financial-Planning Issues For Employees

Bruce Brumberg, Editor-in-Chief
myStockOptions.com
Updated annually, this PowerPoint presentation provides a timely overview of year-end financial-planning topics for stock compensation, including points of importance for employee education and for financial advisors.

In Their Own Words: Financial Advisors On Strategies For Stock Compensation And Company Stock Holdings At Year-End

myStockOptions.com Editorial Team & Contributors
Year-end planning can be tricky. We asked leading financial advisors to provide their ideas on planning for the end of the year and beyond. Read their responses in their own words.

Keep Your Eyes On The Calendar

Robert Gordon
Investment News
Before the end of the year, review any ISO stock you are holding from earlier exercises and consider strategies for the following year. This article offers tips that apply every year. (Registration is required.)

Return to top of this page

UPDATES! What are some year-end strategies for restricted stock, RSUs, and stock options? This is premium content

Decisions in year-end financial and tax planning depend on several factors. In this FAQ, we present several situations and some strategies that many experts suggest. Of course, you should...

Next year I may be in a higher tax bracket. I am thinking about exercising my nonqualified stock options before then to accelerate income into this year. What issues do I need to think about? This is premium content

Before you rush into exercising, you may want to do some calculations with potential future stock prices and tax rates. When you exercise earlier than necessary...

My ordinary income next year will trigger the 3.8% Medicare surtax on investment income, along with higher tax rates on capital gains and dividends. If I were to sell some stock this year, I would avoid these taxes, and I would then repurchase the stock to reset the basis. What are the issues I need to consider? This is premium content

By selling stock at a gain and then buying it back at the current price, you create a new...

For NQSOs or SARs exercised on the last business day of 2014, or for restricted stock that vests on that day, is the income taxable in 2014 or 2015? This is premium content

All exercises with an exercise date in 2014, and all restricted stock with a vesting date in 2014, will be included in 2014 taxes and on your W-2 for 2014, and will count...

At year-end, is there any general way to determine how many ISOs I can exercise and hold before triggering the AMT? This is premium content

One strategy for minimizing AMT is to spread out the exercise of ISOs over...

At the end of the year, should I exercise my in-the-money options and sell the stock to take advantage of netting the gains against my short-term capital losses from this year (or those that were carried forward from last year)? This is premium content

Don't get tripped up by misunderstanding the tax rules. A common mistake is thinking that because you are selling a stock a capital gain lurks somewhere in the tax calculation...

The value of my restricted stock has fallen since vesting. If I sell my shares at year-end, do I get a credit for the income tax I paid at vesting, or do I net the loss against capital gains? This is premium content

The vesting and the sale are separate transactions and generate different types of income. Unless you made an 83(b) election to be taxed at grant, you were first taxed on the stock's value at vesting, which created ordinary income to you. With restricted stock units (RSUs), taxation occurs...

How do stock grants affect Roth IRA contributions and conversions? This is premium content

The grant itself has no impact. The compensation income generated from exercise or vesting can affect...

Are there any stock option or restricted stock strategies for using capital-loss carry-forwards? This is premium content

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...

Will my income from restricted stock vesting be netted against my short-term capital losses from this year (or those that were carried forward from last year)? This is premium content

The value at vesting is all ordinary income. You have capital gain only for the increase in the stock price after vesting. Only this gain at sale can be...

Are there any strategies for paying estimated taxes on income from stock options and restricted stock? This is premium content

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...

What ISO strategies can help minimize AMT liability? This is premium content

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...

I know that my ISO exercises will trigger the AMT for me this year or next. Are there planning strategies related to other tax payments and income? This is premium content

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...

When I hold ISO stock, how far must the stock price drop from the market price at exercise for AMT to exceed what my ordinary income tax would be if I sold the shares this year? This is premium content

Assume that the ISO exercise/hold or other parts of the AMT calculation will trigger AMT. A rule of thumb is...

Earlier in the year, I exercised ISOs, held the stock, and had a big spread from the market price that will trigger AMT. But my company's stock price has dropped below my exercise price. Can I eliminate AMT and even claim a tax loss? This is premium content

As long as you sell the shares on or before December 31, you will...

Can I rescind a stock option exercise and reverse the tax impact? This is premium content

Only in very limited circumstances, and your company needs to allow the rescission. The company would...

Is a Section 83(b) election taxing you on the value of restricted stock at grant ever revocable? Can it be rescinded? This is premium content

The IRS has provided guidance on the limited circumstances in which this is permitted. The Section 83(b) election is irrevocable unless you...

Return to top of page