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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.
The most commonly overlooked asset in financial planning may be surprising: it's compensation. And it's where your clients usually need the most guidance.
Financial Planning - Year-End Planning

Financial Planning › Year-End Planning

Articles

12 Ideas For 2022 Year-End Planning With Stock Compensation (Part 1)

Year-end is a key time for financial and tax planning with stock comp and company shares. Multi-year planning is especially valuable with equity compensation, as you can control the timing of stock sales and option exercises, and you know when restricted stock or RSUs will vest. This article presents actionable ideas to consider. They include looking at the income thresholds that may trigger higher tax rates for option exercises or sales of vested stock.

Year-End Planning: 5 Key Items For Your Stock Comp Checklist This is premium content

NEW! Tick tock. Time is running out for year-end financial and tax planning. This article presents year-end insights from three leading financial and tax advisors with expertise in planning for stock compensation.

7 Year-End 2022 Strategies For Restricted Stock, RSUs, And Performance Shares This is premium content

Podcast included! As part of year-end tax planning, review holdings in restricted stock, RSUs, and performance shares for strategic moves. This article has some ideas.
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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 continued impact of the Tax Cut & Jobs Act and how down and volatile stock prices could influence your decisions.

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

We asked seasoned advisors with expertise in stock comp to provide their ideas on financial and tax planning for year-end 2022 and year-start 2023. Read their responses in their own words.

2022 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.

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

Learn about year-end planning for incentive stock options (ISOs). This article includes guidance on how to take advantage of the special ISO tax treatment and on the alternative minimum tax.

12 Ideas For 2022 Year-End 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.

Making Donations Of Company Stock This is premium content

Nonprofit organizations and charities appreciate donations of shares as much as gifts of cash, and most large nonprofits are experienced in accepting stock donations. This article presents the essentials, including taxation, 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: 5 Points To Know 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 This is premium content

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 year-end 2022 checklist of items to 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 2022 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...

For NQSOs or SARs exercised on the last business day of 2022, or for restricted stock that vests on that day, is the income taxable in 2022 or 2023?

The income will be included in tax year 2022, even if you recognize it on the last business day of the year. However, you should confirm...
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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...

If I sell stock this year, I can avoid higher taxes next year, including the 3.8% Medicare surtax on capital gains. What issues should I consider when I harvest my capital gains? This is premium content

Capital gains harvesting can be effective when all the issues are understood. By selling stock at a gain and then buying it back at the current price, you create a new...

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...

How do the 2018 tax reforms 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...

Is there a way to determine how many ISOs I can exercise and hold without triggering the AMT? This is premium content

One strategy for minimizing AMT is to spread out the exercise of ISOs over multiple years. Following the calculation steps outlined in this FAQ, you can determine what is sometimes called your AMT cushion or crossover point...

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...

My ISO exercise/hold will trigger the AMT. How much would the stock price have to drop for my AMT to exceed my ordinary income tax if I instead sell the shares? 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...
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