Year-End Planning 2020: myStockOptions Newsletter No. 82

Year-end 2020 checklist for stock comp and company shares
Year-end stock option exercise strategy when your 2021 tax bracket will be higher
Special resources on year-end financial and tax planning
How does the election affect 2020 year-end planning?
Special year-end webinar: Dec. 16 (2pm ET, 11am PT)
Year-end CE credits for CEPs, CFPs, CPWAs, CIMAs, and others

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SPONSORS OF THIS ISSUE

• StockOpter: Professional Equity Compensation Analysis Software (see the ad below)
• AdvisorFind from myStockOptions.com: Search this directory for financial, tax, and legal advisors with experience in stock compensation (see the ad below)

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Year-end is a key time for financial and tax planning, especially for the millions of employees who have stock compensation or holdings of company shares. The tax changes introduced in 2018 continue to affect their year-end-planning decisions. Meanwhile, the election presents uncertainty about the future of tax laws that affect financial- and tax-planning strategies. To help, myStockOptions.com provides education and guidance in our section Financial Planning: Year-End Planning.

This newsletter highlights some of our year-end content. All of the content on myStockOptions.com is available through licensing.

Don't want to wait for our quarterly newsletter updates? The myStockOptions.com Blog is a great way to stay informed about new developments in equity compensation. You can also follow us on Twitter and Facebook. In addition, I now have a blog at Forbes.com.

- Bruce Brumberg (Editor-in-Chief)

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The checklist below summarizes what you need for comprehensive year-end planning with stock compensation.

Review:

• exercises, vestings, and ESPP purchases in current year
• holdings of NQSOs, ISOs, restricted stock/RSUs, and company shares
• scheduled vestings in the year ahead, including the end of the cycle for a performance share grant and when payout occurs
• salary contributions allocated for ESPP purchases
• any estimated adjustments needed for the year ahead in the Form W-4 used for salary withholding (the IRS revised Form W-4 for 2020), as your W-4 rate is sometimes applied to stock compensation withholding too

Know:

• deadlines for option or SAR exercises and the expiration dates of option grants
• expected new grants in year ahead and ESPP enrollment/change dates
• trading windows and blackouts, company ownership guidelines, and any post-vest holding-period requirements
• your ability to spread the recognition of income from certain sources over this year and next year
• your marginal tax rate after the 2018 tax reforms, whether the flat rate for federal supplemental withholding that applies to stock compensation will cover it, and what to do if it does not
• whether sales of company stock will trigger short-term or long-term capital gains

Consider:

• your situation, including short-term cash needs that may prompt you to sell company stock and/or exercise options
• whether your decisions should be entirely tax-driven
• your outlook for both your company's stock price and your job
• how comfortable you are with your concentration in company stock and whether you should diversify
• multi-year projections for your income and taxes
• donations in company shares instead of in cash
• Any changes needed in beneficiary designations, when allowed, for your stock compensation and/or your brokerage account holding company shares.
• Whether to pay estimated taxes in the year ahead because of substantial income expected from restricted stock/RSU vesting, NQSO exercises, ISO exercises, or an ESPP purchase/sale.

Collect:

• Company and brokerage firm statements, whether online or in print. You will need them for tax-return reporting.

For year-end financial-planning points to consider with stock compensation, see a related FAQ.

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It is smart to consider the income thresholds that trigger higher tax rates. You are thinking the additional income from the exercise spread will be taxed a lower marginal tax rate this year and will not trigger the 3.8% Medicare surtax on your net investment income.

Example: You and your spouse expect to have modified adjusted gross income (MAGI) of $175,000 in 2020, and you project you will have $250,000 in 2021. This includes about $40,000 per year in dividends and capital gains, which are not subject to the 3.8% Medicare surtax in 2020 because your MAGI is below the $250,000 threshold for joint filers. However, if you exercise NQSOs in 2021 and recognize ordinary income of $50,000, this additional amount will push your MAGI above the $250,000 threshold. You will then have to pay the 3.8% tax on the $40,000 in investment income, along with potentially higher ordinary income rates. The extra $50,000 of income will not trigger these taxes if you exercise in 2020, as your MAGI for the year will still be under $250,000.

Tax Difference Between 2020 Exercise And 2021 Exercise

	2020	2021
Modified AGI	$175,000	$250,000
Dividends and capital gains included	$40,000	$40,000
Income from exercising NQSOs	$50,000	$50,000
Modified AGI + NQSO exercise	$225,000	$300,000
Subject to Medicare surtax?	No	Yes

However, before you rush into exercising, you may want to do some calculations with potential future stock prices and tax rates.To learn more about factors that go into this strategy-building process, see the full FAQ on myStockOptions.

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Below we list some of our content on year-end financial and tax planning, all of which has been fully updated for year-end 2020. To see our entire array of resources on year-end planning, including both articles and FAQs, see the year-end section at myStockOptions.com. For guidance on year-end planning with nonqualified deferred compensation, especially deferral elections for 2021, see the related FAQ at our sibling website myNQDC.com.

Our award-winning content is available with Premium or Pro Membership or through corporate licensing.

Post-Election Year-End Planning: What Financial Advisors And Tax Pros Are Advising Clients About Uncertain Tax Changes
The end of the year is a key time for financial and tax planning. The standard year-end-planning strategy is to defer income into the next year and accelerate deductions into the current year. But tax planning for year-end 2020 could change now that Joe Biden has won the presidency and Democrats may gain complete control of Congress. What does all of this mean for year-end planning in 2020? We asked several financial advisors for their takes.

12 Ideas For Year-End Planning With Stock Compensation (Parts 1 and 2)
Consider year-end or year-beginning tax planning with your stock compensation and company stock holdings. While investment objectives, not tax considerations, should generally drive your decisions, here are several ideas to review to prevent paying more taxes than necessary.

7 Year-End Strategies For Restricted Stock, RSUs, And Performance Shares, by Bruce Brumberg
As part of your year-end and year-beginning tax planning, don't forget to review any grants of restricted stock, RSUs, or performance shares that vested this year, plus other company stock holdings. This article presents strategies many experts suggest.

Year-End Strategies For Employee Stock Purchase Plans: Ideas To Consider, by the myStockOptions Editorial Team
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.

PODCAST! How The 2018 Tax Reforms Affect Year-End Planning For Equity Comp And Company Shares
Employees with stock compensation must consider the changes introduced in 2018 by the "Tax Cuts & Jobs Act". This podcast summarizes how those changes affect your year-end planning, along with strategies that apply every year-end.

Stockbrokers' Secrets: Year-End Planning For NQSOs, Restricted Stock, And RSUs, by John Barringer and Michael Beriss
The time for tax planning is before the year ends; tax season is too late. Learn about several ideas for year-end 2019 that apply to nonqualified stock options (NQSOs) and restricted stock/RSUs.

Stockbrokers' Secrets: Year-End Planning For ISOs, by John Barringer and Michael Beriss
Learn about year-end planning specifically for incentive stock options, including ideas related to the alternative minimum tax.

Leading Advisors Reveal Strategies For Equity Comp And Company Stock At Year-End
Year-end planning can be tricky amid the ongoing impact of tax-rate changes that took effect a few years ago and expected tax reforms in the year ahead. We asked several leading financial advisors for their ideas on financial and tax planning for the end of 2020 and the start of 2021. This article presents their responses in their own words.

Making Gifts Of Company Stock, by the myStockOptions Editorial Team
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, by the myStockOptions Editorial Team
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.

How To Defer Or Pay No Capital Gains Tax On Company Stock Sales: 6 Ways Under The Tax Code, by Bruce Brumberg
The US tax code provides a few perfectly legal ways, depending on your income, financial goals, and even life expectancy, to defer or pay no capital gains tax, maximizing the benefits of your grants and letting you put away more toward your financial goals. If you qualify, consider these moves as part of your year-end planning.

6 Ways The 2018 Tax Reforms Affect Your Stock Compensation And Financial Planning
The 2018 tax changes continue to either directly or indirectly affect stock compensation, whether in financial planning or in stock plan administration (though the core tax treatments have not changed). This article details six provisions that have an impact on the taxation of stock compensation or holdings of company shares and may affect your year-end planning.

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The end of the year is a key time for financial and tax planning. The standard year-end-planning strategy is to defer income into the next year and accelerate deductions into the current year. But tax planning for year-end 2020 could change now that Joe Biden has won the presidency and Democrats may gain complete control of Congress. Biden's tax plan calls for tax increases on high earners.

However, the outlook for tax increases under President Biden is very uncertain. It depends largely on which party holds the majority of the US Senate, which will not be determined until the special runoff election for both of Georgia's US Senate spots in early January, after the end of the year-end-planning season. Even if Democrats do win Senate control to go along with their majority in the House of Representatives, many experts say tax-law changes are unlikely to be a focus of Biden's first year.

Furthermore, in general you never want taxes to be the sole reason for making decisions with your equity comp and company shares. Nevertheless, some financial advisors and estate planners are still expecting higher taxes at some point under the Biden administration and would factor those into multi-year planning. What does all of this mean for year-end planning in 2020?

Among the different parts of Biden's tax plan, these three would have an immediate impact on 2020 year-end planning:

1. The top rate of ordinary income tax would return to 39.6% from 37% for taxpayers with income over $400,000. What remains unclear is whether this income level would be different for couples (married filing jointly) and whether it's $400,000 in adjusted gross income (i.e. before deductions) or in taxable income. If this tax hike seems likely to you in 2021 and you're concerned about higher tax rates, it would lead to accelerating income into 2020 where possible (e.g. exercise nonqualified stock options, receive cash bonuses before year end, do Roth IRA conversions).

2. Biden's tax plan would raise the top rate of capital gains tax from 20% to 39.6% for individuals with over $1 million in yearly income. Capital gains and qualified dividends currently have a top tax rate of 20% (plus the 3.8% Medicare surtax). If this major increase in the top capital gains rate seemed likely to take effect in 2021, it could lead to capital gains harvesting before year-end to sell shares with substantial appreciation, paying tax at the lower capital gains rate, then potentially repurchasing the shares to reset the basis in them (see the FAQ on myStockOptions about this strategy).

Alert: Whenever you sell company stock, you must be careful not to commit insider trading, which is illegal. To prevent insider trading, your company may have blackout periods when you can't trade, often around the end of each calendar quarter, and window periods when you can. As part of any strategy involving stock sales, you need to know when these periods occur.

3. Biden's tax plan would limit itemized deductions to 28% of value, with some deductions phasing out for income over $400,000. That would lead to also accelerating deductions, such as donations, into the current year for high-income taxpayers (the reverse of the usual approach when you expect higher taxes in the future) to maximize them before limits put into place. This concept is explained by financial advisor Jeffrey Levine in the Kitces.com blog.

For financial advisors' views on what the 2020 election means for year-end planning now and in the coming years under the Biden presidency, see our exclusive new article: Post-Election Year-End Planning: What Financial Advisors And Tax Pros Are Advising Clients About Uncertain Tax Changes.

See also a three-part article series on myStockOptions: How Tax Rate Changes Impact Your Stock Grant Strategies. It provides an analytical framework to help you evaluate the impact of an income tax increase at any point in the future, whether the shift is caused by changes in tax law or by an influx of compensation that pushes your income into a higher tax bracket. Part 1 looks at nonqualified stock options (NQSOs). Part 2 examines tax planning for restricted stock and RSUs, which is also useful for analyzing whether to sell or hold NQSO stock from a prior exercise. Part 3 analyzes tax planning for incentive stock options (ISOs).

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Join us on December 16 (2:00pm–3:15 pm ET, 11:00am–12:15 pm PT) for a lively educational webinar: Year-End 2020 Planning For Equity Compensation. This special event will cover year-end planning topics for equity comp, both for financial advisors and for employees with stock comp. Learn strategies for stock options, restricted stock, RSUs, ESPPs, and company stock holdings. The essential topics will be presented in just 75 fast-paced minutes by Bruce Brumberg, Esq., the editor-in-chief and co-founder of myStockOptions.com and a Forbes.com contributor. Bruce is a respected expert on these topics with over 20 years of experience in stock comp education, communications, and training.

The webinar recording and presentation will be available to all registrants, whether they attend the live event or watch later.

Registration is open. The webinar offers 1.5 CE credits for (applications pending):

• Certified Financial Planners (CFPs)
• Certified Equity Professionals (CEPs)
• CPWA and CIMA

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The myStockOptions.com Learning Center has courses of study and exams that offer:

• 35 CE credits for Certified Equity Professionals (over 100% of the total requirement)

• 18 CE credits for Certified Financial Planners (60% of the total requirement)

• 21 CE credits for CPWAs and CIMAs (52.5% of the total requirement)

• Potential self-reportable CPE for Certified Public Accountants (CPAs) and CE for CFA Charterholders (see the Learning Center for information)

Each course of study features podcasts, articles, and FAQs from myStockOptions.com. They are woven into a dynamic, interactive learning tool that teaches the topics in a memorable way. The answer key for each exam also links to relevant content on the site for further reading and learning.

Seven Self-Study Courses

The seven courses offered through the myStockOptions Learning Center focus on nonqualified stock options, incentive stock options, ESPPs, restricted stock/RSUs, SEC law for stock compensation, and financial planning with equity awards. Built on a similar model, the the myNQDC.com Learning Center on nonqualified deferred compensation offers up to 6 continuing-education credits for Certified Financial Planners, 6 Professional Achievement in Continuing Education (PACE) credit hours for CLU® and ChFC® certifications, and up to 12 CPE hours for credentialed ASPPA members.

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