Your Trading Window Just Opened. Should You Sell Company Stock?

Reviewed by Herman Schroeder, CFA

Educational article, not personal advice

As of October 19, 2026.

The short answer

If you work at a public company, you can usually only sell your shares during set windows, often starting a day or two after earnings. Those windows are short, and many people let them pass because the decision feels hard. The fix is to decide before the window opens: how much company stock you want to own, what the extra is for, and how much you will sell this time. Then the window is just a date on the calendar.

Why the window matters

Many public companies block some or all employees from trading for part of each quarter. An open window is not a green light: if you know important company news that has not been made public, you generally cannot trade, even when the window is open. Earnings season runs through late October and November, so many windows open around now and close again a few weeks before the quarter ends.

If you miss it, you wait about three months. A lot can happen to one stock in three months. That is not a prediction. It is just what happens when most of your net worth sits in one company.

Why people freeze

Three thoughts come up again and again.

  • The stock has done well, so selling feels like betting against it

  • The stock has done badly, so selling feels like locking in a loss

  • Taxes feel confusing, so doing nothing feels safer

All three are human. None of them is a plan. Your salary, your bonus, and your unvested shares already ride on the same company. Owning a big pile of vested shares on top of that is a lot of eggs in one basket.

A simple way to decide

Pick a number before the window opens. Some people cap company stock at a share of their total investments. Others pick a dollar amount they are happy to keep no matter what. Either works if you write it down.

Then give the extra a job.

  • A cash cushion or near-term goal, like a home, tuition, or a sabbatical

  • A spread-out portfolio for the long term

  • Paying down expensive debt

If selling everything at once feels wrong, sell a set amount each window. Selling on a schedule means you do not have to guess the perfect price.

Where taxes fit (softly)

Gains on shares held more than one year are long-term and may be taxed at a lower rate. Gains on shares held one year or less are short-term and taxed at ordinary income rates. Restricted stock units (RSUs) are generally taxed as pay when the shares are delivered, usually at vesting. That amount becomes your cost basis, so it is often higher than people think.

That can make it worth checking which lots to sell first. We keep it high-level on purpose. Your tax return decides what applies, so loop in whoever prepares it before a large sale.

A note on preset selling plans

Some employees, especially senior ones, use a preset selling plan, often called a 10b5-1 plan. You set the dates and amounts ahead of time and the sales run on schedule, even outside the window. These plans have rules. You have to set one up in good faith at a time when you have no inside information, and there is a waiting period before the first sale: 30 days for most employees, and 90 to 120 days for directors and officers. If you are an officer or director, your sales may also need to meet SEC Rule 144, including volume limits and, above certain sizes, a Form 144 filing. Your company's legal or stock plan team can tell you if a 10b5-1 plan is available.

Questions to ask yourself

  • When does my next trading window open and close?

  • What share of my net worth is in my employer, counting unvested shares?

  • What number would I be comfortable keeping if the stock fell by half?

  • What job would the money from a sale do?

  • Have I checked holding periods and cost basis with my tax preparer?

How we help

At Schroeder Capital, we work with people who hold a lot of company stock and want a plan they can follow window after window. If your window is open and you are not sure what to do, we are happy to talk it through. You can reach us on our contact page.

Sources

Disclosures

This is general education, not individualized tax, legal, or investment advice. Your company's trading policy, your plan documents, and changes in law or IRS or SEC guidance all matter. Investing involves risk, including the possible loss of principal. Coordinate tax questions with the professional who prepares your return. CFA® is a trademark owned by CFA Institute. Schroeder Capital Management, LLC is not affiliated with CFA Institute.