Clear Money Guide
Guide and tool overview
See the questions covered here, then open the interactive utility.
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Equity Comp in Retirement (RSUs · Options · ESPP)
Updated on
Entering retirement with company stock? Set a target concentration, plan a steady sell-down, and coordinate taxes and blackout windows ahead of time.
The short version
Pick a target concentration (many retirees aim for 5–15% of total portfolio in any one stock). If you’re above it, plan a 3–5 year sell-down with pre-scheduled trades (10b5-1) so emotions and blackout windows don’t derail you.
RSUs are ordinary income when they vest; sales later typically trigger capital gains/losses. Options add deadlines (ISOs 90-day window post-employment is common) and possible AMT.
Mini Concentration Sell-Down Planner
Optional growth assumptions
We show both a simple (no-growth) schedule and an end-of-window target estimate with these growth rates.
Current concentration: 30.0%
Target stock today (no-growth): $120,000 → Reduce by: $240,000
Suggested sell per year (simple): $60,000 (~% of current stock)
With growth (est.): Year-4 target stock ≈ $146,410 (if portfolio 5.0%/yr). Adjust annually.
Educational only. Taxes (basis/holding period), AMT (for ISOs), and blackout/10b5-1 rules can change execution—plan with care.
Options Deadline Helper (ISO / NQSO)
ISO last day to exercise (to keep ISO treatment): —
Company / NQSO last day to exercise: —
Notes: Many plans allow longer than 90 days to exercise, but the ISO window is set by statute, not by the plan — 26 U.S.C. § 422(a)(2) requires you to have been an employee until the day 3 months before the exercise, and an exercise after that no longer qualifies for ISO treatment.
Equity comp decisions are hard to reverse once you sell.
If equity compensation could change taxes, portfolio concentration, or retirement timing, compare the planning scope and advisor fee in annual dollars before you act.
Before you start, what actually happens. The form is run by Kapitalwise, our advisor-matching partner. Kapitalwise sends your details to advisers who pay for the introduction, so expect calls and texts. Clear Money Guide is paid when you submit the form, whether or not you ever hire anyone. The matching service is free to you and there is no obligation to hire anyone.
The Kapitalwise form opens here. You stay on this page.
What happens when you press the button
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A simple 4-step plan
- Inventory & deadlines. List RSUs (vest dates & tax lot basis), ESPP shares (lots), and any options (ISO/NQSO) with post-employment exercise deadlines.
- Pick a concentration target. Choose a ceiling for single-stock risk (many retirees use 5–15%).
- Build a sell-down schedule. Use the tool to set annual sales over 3–5 years. Re-check once a year and around big market moves or new vests.
- Automate and coordinate taxes. Set a 10b5-1 plan if you’re an insider; line up RSU tax lots, capital-gains holding periods, and option exercises (watch AMT for ISOs).
Tactics that keep things calm
- Sell-to-cover vs. net shares: Understand how vesting taxes get paid and what you still owe at filing. See RSU: Sell-to-Cover vs Net Shares.
- Bracket awareness: Time larger sales in years with extra tax room (pair with Roth Conversion Windows planning).
This is educational content, not tax advice. Confirm details with your plan documents and a tax professional.
Common questions
What if I’m “retirement eligible” at my company? Some plans accelerate or continue vesting—others don’t. Check your equity plan’s retirement provisions.
How do blackout windows affect me? Insiders often face trading blackouts around earnings. Use a 10b5-1 plan so trades execute automatically even during blackouts.
Do I sell RSUs right at vest? Many retirees sell a portion on vest to avoid concentration creep, then pace remaining sales to manage taxes and risk.
What about options? Track exercise deadlines (ISOs often 90 days post-employment). ISOs can trigger AMT if you hold after exercise; NQSOs are ordinary income at exercise.
Methodology
How this page calculates and what to expect
- Dollar-first outputs. We convert percentages and rules into dollars so you can compare choices quickly.
- Fee tools (AUM · Fixed · Retainer · Hourly).
- AUM fees use an annual average balance ((start+end)/2). Tiered schedules are treated as marginal (like tax brackets).
- Contributions are applied at year-end; returns compound annually; “Deduct fees from portfolio” subtracts fees from assets (toggle changes this).
- We ignore taxes and platform/trading costs unless stated. Results are planning estimates, not exact billing replicas.
- Retirement & tax windows (IRMAA · SS taxability · RMD · QCD).
- Calculators use current-year values you enter (caps, surcharges, thresholds) and simplify agency rules for planning.
- Outputs are estimates to help you stay under a line (bracket, cap, or threshold). Confirm details before acting.
- Data freshness. This page’s content was last reviewed on . Some thresholds change annually—update inputs as needed.
- Educational only. Not tax, legal, or investment advice. For specifics, talk to a fiduciary advisor.
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