Should I sell my company stock?
By Adam Kasick | Wealth Advisor | Updated September 2026
Maybe, but I would not start with a blanket decision to sell. The better first step is to understand how much of your financial life depends on the stock, what selling would cost in taxes, what keeping it exposes you to and what alternatives exist between holding everything and selling everything.
Here's how I'd think about it.
Concentration is not automatically a mistake. It becomes a planning problem when we cannot explain why the position is still the right size, what risk it creates or what would happen to your goals if the asset fell substantially.
What could change the answer?
Your cost basis, tax situation, time horizon, liquidity needs, other assets, emotional attachment to the company and how much downside your overall plan can absorb all matter.
What would I avoid?
Selling simply because a pie chart says you are concentrated, or holding simply because the stock has done well in the past. Neither is a financial plan.
Here's what I'd want to know about you.
- What percentage of your financial life depends on this asset?
- What is your cost basis and where is the asset held?
- When will you need money from the portfolio?
- What would a major decline change for you?
- What taxes or other constraints would selling create?
I don't want a pie chart to make the decision. I want you to see the tradeoffs clearly enough to make the concentration intentional.
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