If a big chunk of your net worth is tied up in one company's stock, you already know the feeling: gratitude that the equity has done well, and a quiet worry about what happens if it doesn't. That tension is normal. The goal isn't to eliminate it, it's to make deliberate decisions instead of letting inertia decide for you.
Concentration is the real risk
The single biggest risk in an equity-heavy portfolio isn't taxes, it's concentration. When one position drives most of your wealth, your financial future is hitched to one company's fortunes. Diversifying isn't a lack of faith in your employer. It's simply refusing to let one outcome decide everything.
Three questions to anchor the plan
Before selling a single share, we walk clients through three questions:
- When does it vest, and when can you sell? Vesting schedules and trading windows shape the entire timeline.
- How much of your net worth is in this one stock? Once a position passes roughly 10 to 20 percent of your liquid wealth, it deserves a hard look.
- What is the real tax cost of selling? RSUs and options are taxed very differently, and the holding period matters.
From there, a measured selling plan, often spread across tax years, can bring concentration down without triggering an avoidable tax bill in any single year.
Make it boring, on purpose
The clients who do best with equity comp tend to treat it like a system, not a series of one-off bets. A written plan, a target allocation, and a schedule remove emotion from the decision. That's the whole point: turn a stressful, all-at-once choice into a series of small, sensible ones.
