The Moment
You have 3, 4, or more RSU grants from different years, each vesting on its own schedule — quarterly, annually, or on cliff dates. Some grants are up significantly from their grant date. Others are underwater. The complexity makes it easy to do nothing — which is the most dangerous choice.
The Systematic Approach
Rule 1 — Sell every batch within 5 business days of vesting. Apply this rule to every batch, regardless of the stock price, market conditions, or your feelings about the company. Consistency removes emotional decision-making. If your company has trading windows, sell on the first available day after the window opens.
Rule 2 — Track total company stock exposure. Create a simple spreadsheet: - Vested shares held (value at current price) - Unvested shares (estimated value at current price) - Your net worth (all assets minus all liabilities) - Company stock as % of net worth
Target: vested company stock under 10% of net worth. Unvested stock is less controllable, but knowing the total exposure keeps you aware of the risk.
Rule 3 — Treat each vest independently. Do not anchor to the grant price. A batch granted at $200/share that is now at $150 is not "losing money" — you paid $0 for those shares. At vesting, you received $150/share of compensation. Sell it and invest in something diversified. The grant price is irrelevant to the sell decision.
Rule 4 — Automate if possible. A 10b5-1 plan automates selling across all vesting dates. Set it once, forget it. No trading window constraints, no emotional interference.
Run Your Numbers
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$50,000 Windfall Allocator
What to explore next
- →How do I set up a 10b5-1 plan for multiple grants?
- →How do I track my total company stock exposure?
- →Can I harvest tax losses from underwater RSU batches?
Frequently Asked Questions
Some of my batches are underwater — should I hold those?
The vesting price is your cost basis for tax purposes. If the stock has declined since vesting, selling creates a capital loss you can use to offset other gains (tax-loss harvesting). An underwater RSU batch is actually an opportunity — sell, harvest the loss, and reinvest in a diversified fund.