You Vested a Fortune in One Stock. Now What?
Henry Supinski, ChFC® · 5 min read · July 2026
If a big chunk of your net worth sits in your employer's stock, you didn't necessarily choose that. It happened one vest at a time. Here's how to think clearly about reducing that risk without a rushed, tax-inefficient sale.
Concentration Sneaks Up on You
Nobody wakes up one day and decides to put 40% of their net worth into a single stock. It happens gradually, one vesting event at a time, while the share price quietly climbs. By the time it's a problem, it's also the best-performing asset you own, which makes it psychologically hard to touch.
A Rule of Thumb, Not a Rule
A common guideline is to keep any single stock position under 10% to 15% of your investable net worth. That's a starting point, not a mandate. The right number for you depends on your other assets, your risk tolerance, your conviction in the company, and how much of your future income (salary, bonus, and future grants) is already tied to the same employer.
Ways to Reduce Concentration Without a Single Painful Tax Bill
- Sell in stages over multiple years to spread the capital gains across tax brackets.
- Direct new vests to cash and rebalance, rather than selling old shares with more embedded gain.
- Use a 10b5-1 plan to automate the selling and remove the temptation to time it.
- Consider donating highly appreciated shares to a donor-advised fund if charitable giving is part of your plan.
- For very large positions, exchange funds can diversify exposure without triggering an immediate sale.
The Question That Actually Matters
Would you buy this stock today, with cash, if you didn't already own it? If the answer is no, the reason you're still holding it is usually inertia or a fear of the tax bill, not conviction. A plan built around your whole financial picture, not just this one stock, is the way out of that loop.