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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Ten Financial-Planning Rules For Restricted Stock And RSUs This is premium content

While grants of restricted stock and RSUs are conceptually simple, financial planning for them can be complex. This article presents the essential financial-planning points that you should consider before your restricted stock or RSU grant vests.

Ten Financial-Planning Rules Everyone With Stock Options Needs To Know

Managing stock options is one of the most complex financial-planning challenges you may face. The 10 guidelines in this article will help you get the most out of your option grants: setting goals, stock option valuation, exercise timing, job-loss considerations, understanding the taxation, and much more.

Ten Financial-Planning Rules Every ESPP Participant Should Know This is premium content

Employee stock purchase plans (ESPPs) are a super deal. However, the related taxation and financial planning can be deceptively complex. This article presents the essential points that you should understand before you participate in your company's ESPP.
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Six Ways Tax Reform Affects Your Stock Compensation And Financial Planning

Podcast included! The Tax Cuts & Jobs Act has provisions that affect stock compensation, whether in financial planning or in stock plan administration. This article details six with an impact on the taxation of stock compensation or holdings of company shares.

UPDATES! The Impact Of Tax-Law Changes On Stock Option And Restricted Stock Strategies This is premium content

Podcast included! While in 2018 the Tax Cuts & Jobs Act superseded many prior tax provisions, other tax provisions introduced in previous legislation (such as the Affordable Care Act, i.e. Obamacare) remain in place. Income thresholds for the tax brackets trigger higher tax rates, so it is wise to monitor the tax impact of income-generating events stemming from stock compensation. This article suggests strategies for minimizing their impact.

Using Behavioral Finance To Shape Planning For Stock Compensation This is premium content

Emotions can have a powerful impact on financial decisionmaking. The study of behavioral finance, i.e. how people make decisions about investments and other financial matters, can help you to develop a sensible approach to stock compensation and holdings of company stock.

How To Avoid Mistakes And Create Wealth With Your Stock Options This is premium content

Podcast included! Stock options can be very lucrative if handled properly, but there are situations in which people can easily make mistakes. In this article I discuss the most common mistakes I see.

A Holistic Approach To Managing Equity Compensation And Setting Goals This is premium content

Podcast included! Planning for equity compensation begins with identifying the role stock grants will play in your life, whether for retirement, college funding, or other goals. This article offers points to consider for three different types of investors.

Stockbrokers' Secrets: Equity Compensation Strategies For Volatile Markets

Market volatility and declines rattle even the most experienced holders of stock compensation (and their advisors). This article presents topics I find myself discussing over and over again with my best clients.

Employee Stock Purchase Plans And Your Financial Planning (Part 2) This is premium content

Employee stock purchase plans (ESPPs) are changing in many ways, largely in response to accounting rules. For Part 2, asked financial and wealth advisors what they are recommending to clients about ESPP participation.

Stockbrokers' Secrets: Restricted Stock And Performance Shares This is premium content

Many companies have turned away from stock options and begun to make outright stock grants that must vest before the shares can be issued. For employees, these grants have added a new layer of complexity to their equity compensation. This article presents six questions I get all the time from clients who have received restricted stock, restricted stock units, or performance shares.

Restricted Stock: Tax, Financial, Estate, And Retirement Planning (Part 1) This is premium content

Podcast included! Understand financial planning for restricted stock and RSUs. Part 1 discusses the growing popularity of these grants, their special features, and the related tax planning.

Strategic Planning With Roth IRAs And Stock Compensation (Part 1) This is premium content

Could the Roth IRA be your greatest opportunity for accumulating tax-free growth? Well, as with most strategic-planning issues, it all depends. Part 1 of this two-part article series looks at the rules and factors to consider in a Roth IRA conversion.

Preventing Irrational Decisions About Selling Company Stock Or Exercising Options

Whether you are a novice or advanced investor, it can be hard to decide what to do with your company's stock grants. Should you exercise options now or wait? Should you hold company stock at vesting or sell it and reinvest? Behavioral economics and investor psychology offer insights that can help you develop a personally acceptable approach.

A Financial Advisor's View Of Your Stock Plans This is premium content

Podcast included! Rather than a guarantee, today's benefit plans offer only an opportunity to attain financial security. The planning decisions you make with equity awards are crucial.

Getting The Most From Your Stock Options This is premium content

Podcast included! Stock options are a major element of your long-term incentive compensation, offering tremendous potential to accumulate personal wealth. Given your stock options' complexity, it’s essential to develop a strategy to realize their full potential.

Stockbrokers' Secrets: Stock Option Strategy (Part 1)

My clients want to exercise options shortly after they vest for a significant purchase, like a fancy boat or a sports car. The most expensive boat or car I can imagine is the one bought with your just-vested options. Tips I tell clients include not exercising too soon or waiting too long.

Stockbrokers' Secrets: Stock Option Strategy (Part 2) This is premium content

I see too many smart people who have substantial gains in their stock options do dumb things, as I explained in my first article. Here are more of the rules I try to teach my clients, which can act as a guide for you, too.


What are the top 10 questions that I should answer before making a financial plan with my stock compensation?

You need a financial plan that considers your goals for the income, identifies decisions you must make with your grants and acquired shares, and factors in the related tax consequences. Start by knowing the answers to the following 10 questions...

My restricted stock will vest soon. Should I sell the shares at vesting or hold them?

When restricted stock, restricted stock units, or performance shares vest, whether you sell or hold the shares depends on various factors. Some of them are under your control...

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...
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What are the 10 most important financial-planning rules for employee stock purchase plans?

Before you participate in your company's employee stock purchase plan (ESPP), understand the following essential points for financial planning with ESPPs...

What are the top 10 questions related to retirement planning that I should ask about my stock options, restricted stock/RSUs, or ESPP participation?

Retirement savings can be significantly boosted by equity compensation. When factoring stock options, restricted stock/RSUs, or ESPPs into your retirement planning, you should know the answers to the following questions...

I have vested stock options. What should I do: exercise and hold, exercise and immediately sell, or wait to exercise? This is premium content

This is a difficult question that only you can really answer, as your exercise timing depends on a number of personal factors unique to you...

I have more than one stock option grant, and they are at different exercise prices. Which one should I exercise first? This is premium content

Most option plans do not prescribe the order of option exercises, which is usually up to you...

Are there financial-planning strategies for NQSOs? This is premium content

There is no universal NQSO planning for everybody. With that said, we present some general advice from experts...

My company's stock price recently fell dramatically, but I expect it to rise again soon. Are there any NQSO strategies (or mistakes to avoid) in a market upturn? This is premium content

When the stock market rebounds after a fall, one of the most common mistakes among optionholders is exercising too early to grab quick profits...

I plan to exercise options for stock that pays dividends. Are there any exercise strategies or at least mistakes to avoid? This is premium content

To receive a dividend you must own a stock on the record date, so you want to be aware of the ex-dividend date. Also consider...

To seek financial aid for children's college tuition, I report income and assets on the Free Application for Federal Student Aid (FAFSA). Should I list my stock grants? At what value?

As long as the student is considered a dependent of the parent for financial-aid purposes, the parent does have to report stock options on line...