Financial Planning
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.
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Articles

12 Ideas For 2019 Year-End Planning With Stock Compensation (Part 1)

Podcast included! Year-end is a key time for financial and tax planning with stock compensation and holdings of company shares. When you are evaluating whether to exercise stock options or sell shares from vested restricted stock/RSUs or an ESPP, you want to consider the thresholds that may trigger higher tax rates for you either this year or next. This article provides guidance and ideas for year-end planning with equity compensation and company stock holdings.

7 Year-End Strategies For Restricted Stock, RSUs, And Performance Shares This is premium content

Podcast included! As part of your year-end 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 This is premium content

Podcast included! 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.
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NEW! Leading Advisors Reveal 2019 Year-End Strategies For Equity Comp And Company Stock

We asked several financial advisors to provide their ideas on year-end and year-beginning planning. Read their responses in their own words.

12 Ideas For 2019 Year-End Tax Planning With Stock Compensation (Part 2) This is premium content

Podcast included! Understand the core concepts in year-end 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.

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

Learn about year-end planning for NQSOs and restricted stock/RSUs, including the impacts of the tax reform that took effect.

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

Learn about year-end planning for incentive stock options. This article includes ideas related to the alternative minimum tax.

Making Gifts Of Company Stock This is premium content

In addition to being an effective form of generosity, gifting shares can play a role in financial and tax planning for your equity compensation and company stock. This article presents the basics that you need to know when you are contemplating gifts of shares acquired from stock options, restricted stock/RSUs, or employee stock purchase plans.

Making Donations Of Company Stock This is premium content

Nonprofit organizations appreciate donations of shares as much as gifts of cash, and most large nonprofits are experienced in accepting stock donations. This article presents the basics that you need to know when you are contemplating charitable donations of shares acquired from stock options, restricted stock/RSUs, or employee stock purchase plans.

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

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.

Presentation! Year-End Tax And Financial Planning: What Employees And Their Advisors Should Know

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.

FAQs

What should be on my 2019 year-end checklist of items to review, know, and consider about my stock compensation?

The checklist in this FAQ summarizes all you should review, know, think about, and collect...

What are some key planning strategies at year-end 2019 for restricted stock, RSUs, and stock options?

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...

For NQSOs or SARs exercised on the last business day of 2019, or for restricted stock that vests on that day, is the income taxable in 2019 or 2020?

The income will be included in tax year 2019, even if you recognize it on the last business day of the year. However, you should confirm...
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How does tax reform continue to affect year-end planning? This is premium content

Employees with stock compensation must consider the tax changes introduced by the Tax Cuts & Jobs Act (TCJA). There are some key points to know...

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...

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...

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...

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...

If I hold ISO shares after the year of exercise, how far must the stock price drop from the market price at exercise to trigger the AMT? 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...