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.

Articles

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

Podcast included! After tax reform, financial planning at year-end 2018 is more important than ever. 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 trigger higher tax rates. 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 2018 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 in 2018, 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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12 Top Ideas For Year-End Tax Planning With Stock Compensation (Part 2) This is premium content

Podcast included! Understand the core concepts in 2018 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 in 2018.

Leading Advisors Reveal Year-End Strategies For Equity Comp & Company Stock

We asked several financial advisors to provide their ideas on planning for year-end 2018 and beyond. Read their responses in their own words.

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 2018 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 2018 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...

NEW! How does tax reform affect year-end planning in 2018? This is premium content

This is the first year-end season when employees with stock compensation must consider the tax changes introduced in 2018 by the Tax Cuts & Jobs Act (TCJA). There are some key points to know...
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For NQSOs or SARs exercised on the last business day of 2018, or for restricted stock that vests on that day, is the income taxable in 2018 or 2019?

The income will be included in tax year 2018, even if you recognize it on the last business day of the year. However, you should confirm...

UPDATES! 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...

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...

UPDATES! 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...

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...