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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

Financial Planning explores various approaches to making the most of stock grant gains while minimizing taxes. The coverage includes the role of stock grants in gifts, estates and trusts, dividends, hedging, and more.

Test Your Knowledge Test and improve your knowledge with our Financial Planning quiz and its study guide in the answer key.

Want to learn more about financial planning for equity compensation? Visit our podcasts page for interviews with some of our expert contributing authors.

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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.

Your Company Stock: The Importance Of Diversification This is premium content

Laura Tanner, PhD, CFP®
Podcast included! Through the author's personal example, this article presents the dangers of a concentrated stock position, discusses why diversification may be hard for employees with shares from equity compensation, and explores strategies for preserving your net worth.

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.

In Their Own Words: Advisors On Strategies For Equity Compensation And Company Stock At Year-End 2014

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

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.

American Taxpayer Relief Act And Medicare Surtax: Impact On Stock Option And Restricted Stock Strategies This is premium content

Alan B. Ungar
Podcast included! The American Taxpayer Relief Act and the Affordable Care Act introduced tax-rate increases you must consider in deciding when to exercise stock options, when to sell company shares, and how to plan around income from restricted stock/RSU vesting.

Tax Planning For Options, Restricted Stock, And ESPPs After 2013 Tax Law Changes: High-Income Taxpayers Impacted Most (Part 1)

Tom Davison and William Whitaker
The beginning of 2013 brought notable shifts in tax rates for people at higher income levels. Part 1 surveys the important tax changes and considers their impact on planning.

The Equity Compensation Planning Dilemma For Corporate Executives This is premium content

Geoffrey M. Zimmerman, CFP®
Podcast included! Executives, as corporate insiders, must perform a delicate balancing act to meet the needs, demands, and perceptions of the various constituencies interested in their company's stock. This article looks at these concerns and explores ways to manage them that can improve the chances of achieving financial goals.

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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 income next year will trigger higher taxes, including the 3.8% Medicare surtax on capital gains. If I sell stock this year, I can avoid these taxes and then next year repurchase the stock to reset the basis. What issues should I consider? This is premium content

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

What's the impact of the recent tax increases on my restricted stock grants? This is premium content

Increases in tax rates indirectly affect the value of grants. Most importantly...

What is a concentrated stock position, and what can I do to protect myself and get cash for other purposes? This is premium content

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...

I have various stock option grants with vested options. Do I need to exercise first my oldest grants or my oldest vested options?

There's no requirement for which vested options you must exercise first. The decision of which options to exercise first is part of your...

My company is now granting restricted stock, and the current share price is much lower than I think it will be in a few years. Any tax-planning ideas? This is premium content

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...

If my company requires me to have a foreign bank or brokerage account because of the stock plan, what do I need to know about the FBAR and FATCA reporting rules? This is premium content

Under the FBAR and FATCA rules, you may have special IRS reporting requirements if you hold assets in a bank outside the US. This FAQ explains the requirements and the severe penalties that the IRS imposes for noncompliance...

I work and live in the United States but have non-immigrant alien status (L1 visa). My stock options vested when I worked in my home country. I plan to exercise the options while living in the US. Will I have to pay taxes to the IRS and/or the US state where I live? This is premium content

If you are a US resident at the time of exercise, the options are taxable in the United States, so you will owe federal tax on...

What is backup withholding? How do I prevent it or recover it? This is premium content

Backup withholding is a form of tax withholding on income from stock sales, along with interest income, dividends, or other types of payments that are reported on Form 1099. Your brokerage firm is required to make backup withholding if you are...

How does a non-US resident reclaim US backup withholding? This is premium content

If you are a nonresident alien and do not complete and file Form W-8BEN with the IRS upon receiving stock-sale proceeds, such as those stemming from equity awards, your brokerage firm will assess backup withholding on the proceeds. To reclaim backup withholding, take the following steps...

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