What To Do When Your Stock Options Vest

What To Do When Your Stock Options Vest

April 17, 2019

Do you have employee stock options? Here’s a better question: If your compensation package includes stock options, do you know how they benefit you and fit into your financial plan? Stock options are complicated, to say the least. Between taxation, diversification, and more fine print than you know what to do with, it would be easy to stick your head in the sand and not take advantage of your stock options. But like anything to do with your finances, the more information you have, the better decisions you can make. If you’ve been granted stock options and stayed with your company long enough for them to vest, read on.

How Do Employee Stock Options Work?

As a primer, employee stock options offer the employee the right to buy a certain amount of company shares at a predetermined price for a specific period of time. Your options will have a vesting date, which means that after a certain amount of years, you can exercise your stock options.

Let’s say you work for company XYZ and they have issued employee stock options to you at $50. In this scenario, you would have the right to purchase 1,000 shares of XYZ stock at $50 (the grant price) after three years (the vesting period) and within ten years (the expiration date) of the grant date. Until your options vest, there’s nothing for you to do. But once you reach that magical date, it’s time to act.

What Can I Do With Vested Stock Options?

Once your options vest, there are really only three routes you can take. Option #1 is to do nothing and just hang onto them. This is the easiest path, as it requires no effort on your part. On the downside, you also receive no immediate financial reward.

Option #2 is for you to exercise the options and hold the stock. This is where you go ahead and make use of your options to buy stock at the discounted exercise price. Once you’ve purchased the stock, you keep it as a part of your portfolio. This will increase your portfolio value, but you will receive no immediate cash reward.

Option #3 is to exercise the options and then immediately sell the stock. This allows you to quickly convert your options to cash for use in other areas of your life.

Things To Consider When Making Your Decision

So, you have three different possible routes that you can take once your options vest. Which is best? The best choice for you will depend on a variety of factors. Here are some things to take into consideration when making your decision.

Asset Allocation

Do you want to own company stock? If the answer is no, then Option #2 is not the one for you. If you think your company’s stock will increase in value, then you may want to go with Option #1 and wait to see how much of a gain you can realize. There is a risk to waiting, though, as the stock price could decrease. If you just want to take the money and run, you’ll probably opt for Option #3.

If you do want to own company stock, then Option #1 or Option #2 are for you. Your tax situation and the type of stock options they are will influence which of those two choices is best.

When contemplating whether or not you want to own company stock, you should consider diversification. Owning company stock does not only impact the diversification of your portfolio, but also your net worth and income-earning potential. If your company fails, it’s not just the stock that you may lose out on, but you could also lose your job and source of income.

Cash Or Cashless Exercise?

With stock options, you’re not actually given the stock. Rather, you’re given the right to purchase stock at a specified price (hopefully lower than market value at the time of vesting). Since it is a purchase, you need funds to make the purchase. If you have enough cash, you can pay for the stock and/or tax withholding with it in what is called a cash exercise.

Even if you don’t have cash, you can still exercise your options in what is called a cashless exercise. In a cashless exercise, a portion of the stock shares are sold in order to cover the cost of the purchase and/or taxes. You don’t need any cash up front, but you end up with fewer shares in the end.

Whether you do a cash or cashless exercise will first depend on whether or not you have the cash available to you. If you don’t, you have no choice but to go with a cashless exercise. Even if you do have the cash, you may choose to reserve it for other purposes and still do a cashless exercise.


Stock options are compensation and are therefore taxed. The kind of options they are, whether Incentive Stock Options (ISOs) or Non-Qualified Stock Options (NSOs), will determine how they are taxed. There’s a good chance that your stock options are also subject to the Alternative Minimum Tax, or AMT.

Since the tax impacts of stock options can be significant, it is important to work with a financial professional with experience in this area when deciding when and how to exercise your stock options.

How We Can Help

Do you have a plan for how to use your stock options? If you have stock options that you need help figuring out or other financial questions that you simply don’t have the time to answer on your own, I can help you. Call my office at (949) 221-8105 x 2128, or email me at michael.loo@lpl.com to schedule a meeting today!

About Mike Loo

Mike Loo is an independent financial advisor with more than 20 years of experience in the financial services industry. His mission is to make a meaningful impact on the lives of clients and the people they care most about, help them make educated decisions with their money, and build a strong financial foundation for both themselves and their next generation. Mike is committed to meeting a high standard of excellence, taking the time to listen to clients’ needs, and designing strategies that aim to help clients save money and reduce debt. He seeks to fit a client’s investments into their life and educate them so they’ll understand their investments. To learn more about how Mike may be able to help, connect with him on LinkedIn, call his office at (949) 221-8105 x 2128, or email him at michael.loo@lpl.com.

Mike Loo is a registered representative for LPL Financial (LPL) and an Investment Advisor Representative (IAR) for Trilogy Capital (TC). Securities offered through LPL, Member FINRA/SIPC. Investment advisory services offered through TC, a Registered Investment Advisor. TC markets advisory services under the name of Trilogy Financial (TF), an affiliated but separate legal entity. TC and TF are separate entities from LPL.

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk.