Employee Stock Options

Can I extend my exercise window if I’m not ready to pay the taxes?

by Zajac Group | Last updated Mar 24, 2026 | Employee Stock Options, FAQ

Rarely. Unless your company has a specific policy for ";retirement eligibility" or an extended window for all former employees (like some pre-IPO startups), the 90-day rule is usually rigid. However,...

Can I do a “cashless exercise” during my post-termination window?

by Zajac Group | Last updated Mar 24, 2026 | Employee Stock Options, FAQ

If your company is public and has a liquid market, yes. This is often the best way to handle the window if you don't want to use your own cash....

What happens to my ISOs if I wait until day 91 to exercise?

by Zajac Group | Last updated Mar 24, 2026 | Employee Stock Options, FAQ

If your plan allows for an exercise after 90 days, your ISOs will have been converted into NQSOs. You will lose the ability to qualify for long-term capital gains on...

Does my 90-day window start the day I give notice or my last day of work?

by Zajac Group | Last updated Mar 24, 2026 | Employee Stock Options, FAQ

Typically, the clock starts on your official "termination date"—your last day of active employment. However, you should check your specific plan agreement.

What to Know About Your Post-Termination Exercise Window for Equity Compensation

by Daniel Zajac, CFP®, EA | Last updated Mar 24, 2026 | Employee Stock Options

Equity compensation is an effective tool for attracting and retaining highly qualified employees. But if you’re like most Americans, it’s unlikely you’ll remain with your current employer all the way...

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A Comparison of Employee Stock Options vs. Restricted Stock Units

by Daniel Zajac, CFP®, EA | Last updated Mar 14, 2026 | Employee Stock Options, Restricted Stock

Employee stock options and restricted stock units are collectively discussed under the umbrella of equity compensation. As equity compensation, they have some similarities. Yet they also have a lot of...

Comparing Incentive Stock Options and Non Qualified Stock Options

by Daniel Zajac, CFP®, EA | Last updated Mar 14, 2026 | Employee Stock Options, Incentive Stock Options, Non Qualified Stock Options

Non-qualified stock options and incentive stock options are the two types of employee stock options that you may receive as part of your compensation package. While they have some similarities,...

How to Choose if Offered Restricted Stock Units or Non Qualified Stock Options

by Daniel Zajac, CFP®, EA | Last updated Mar 14, 2026 | Employee Stock Options, Non Qualified Stock Options, Restricted Stock

Some employers may allow you to choose how you receive your equity compensation. They may allow you to receive it all in NQSOs or all in RSUs or they may...

4 Key Highlights of Employee Stock Options

by Daniel Zajac, CFP®, EA | Last updated Jul 7, 2025 | Employee Stock Options

Employee stock options are a powerful tool for businesses to provide an incentive for key employees and those who contribute to a company’s success. Stock options give you the right...

What Happens to Your Employee Stock Options When You Leave Your Company?

by Daniel Zajac, CFP®, EA | Last updated Jul 7, 2025 | Employee Stock Options

Even if you don’t have plans to leave anytime soon, it’s not unreasonable to consider what happens to your employee stock options when you no longer work for your current...

How Do You Pay the Exercise Cost When You Exercise Your Employee Stock Options?

by Daniel Zajac, CFP®, EA | Last updated Jul 7, 2025 | Employee Stock Options

If you have employee stock options, you’ve likely spent time considering how and when to turn the value of those options into cash proceeds you can actually use. To turn...

How to Use a Stock Swap to Exercise Your Employee Stock Options

by Daniel Zajac, CFP®, EA | Last updated Jul 7, 2025 | Employee Stock Options

A stock swap can be a great strategy to use if you have employee stock options you’d like to exercise and hold. It allows you to use the fair market...

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