What Happens to Your Equity When You Stop Working? Retirement Planning for San Diego Tech Professionals
We work with employees of Intuit who are turning years of concentrated equity into a retirement they can actually plan around.
The Intuit employees I sit down with have usually done the hard part already. Years of vesting, an ESPP they kept enrolling in without revisiting it, a 401(k) somewhere in the background. What almost nobody has is a plan for turning all of that into income once the paychecks stop. That last part is what these conversations end up being about.
This page is for you if you're asking:
- How do I turn concentrated stock into income I can actually rely on?
- The ESPP position I never really chose. Keep it, or unwind it?
- When should the 401(k) move, and in which tax year?
- If I retire before Medicare, what covers the gap?
BAS Financial is not affiliated with, endorsed by, or sponsored by Intuit. Company names are used only to describe the employer benefit structures discussed.
Fifteen years of shipping product buys you a lot of stock. It does not automatically buy you a retirement.
Three Decisions That Compound Over a Career
Vesting and the Tax Bill
Shares count as ordinary income the day they vest, whether or not you sell a single one. The part that catches people is the withholding, which is applied at a flat supplemental rate that often sits below what a high earner actually owes. Several vesting events in one year and the shortfall stops being a rounding error. Your CPA is the right person to size it.
What Happens After the ESPP Purchase
Enrolling is the easy decision and most people make it once, then never revisit it. Every offering period after that quietly adds to a position nobody chose deliberately. Whether to sell at purchase, hold for the tax treatment, or stop contributing altogether is the decision that actually moves the outcome, and it is worth making on purpose rather than by autopilot.
How Much Rides on One Ticker
Nobody sets out to put half their net worth into their employer. It arrives quietly, one vesting event at a time, over a decade. There is no universally correct percentage, and I am not going to invent one. What matters is that you know your number deliberately, because a figure you chose is a position and a figure that accumulated is an accident.
Within Five Years of Retiring?
Almost every piece of equity-compensation advice is written for the years when you are still building. Inside five years the questions invert. Concentrated stock has to become income on a schedule you control rather than one the market picks. A rollover lands in a specific tax year and that year is a choice. Stock sales and a Social Security claiming decision can collide if they happen in the same window. And if you stop working before sixty-five, something has to cover healthcare until Medicare starts, which is itself income that can push your future premiums higher.
If plan costs are the thing on your mind, the 401(k) Fee Review is a narrower place to begin.
What Happens Next
Email, within a few minutes. Nothing on your calendar and nobody following up by phone.
Short enough for one sitting. Skip to the part that matches where you are in the timeline.
If it surfaces something you want a second opinion on, the booking link is further down.
"I don't have millions sitting in an account. Is this really aimed at me?" It is aimed at exactly that situation. Most of the people I sit with are mid-career, hold a meaningful position in one stock they never consciously built, and have a retirement date somewhere on the horizon that has started to feel less theoretical. If that is you, the questions on this page are already yours whether or not anyone has helped you look at them.
What the compensation portal leaves out
Your compensation portal is excellent at telling you what vested, when, and what it was worth that day. It has nothing to say about how those shares, the ESPP position behind them and the 401(k) behind that should behave as one thing across the next fifteen years. Nobody is paid to answer that question for you internally. That is the conversation I have.
Common Questions From San Diego Tech Professionals
My RSUs vested and I didn't sell anything. Why do I owe taxes?
Because vesting is the taxable event, not selling. The value on the day the shares release counts as ordinary income and lands on your W-2 whether the shares stay put or not. The reason it stings is usually withholding: it comes out at a flat supplemental rate that frequently sits below a high earner's actual bracket, so the gap only appears at filing. Worth modelling with your CPA before the year ends rather than in April.
Should I sell my ESPP shares at purchase or hold them?
The honest starting point is how much of the same stock you already own through vesting, because the ESPP is rarely the position that matters most. From there it comes down to your tax picture and whether you would buy that much of one company deliberately at today's price. Both selling and holding are defensible. Repeating the cycle for eight years without ever asking the question is the expensive option.
How much company stock is too much?
There is no universal figure and I am suspicious of anyone who offers one. What I can tell you is that almost nobody arrives at their concentration on purpose. It accumulates through a decade of vesting while attention is elsewhere. The useful exercise is working out the number you actually hold, then deciding whether you would choose it today with fresh money.
Five years out. What actually needs deciding first?
Four decisions, and each one constrains the others. Turning concentrated stock into income on a timetable you control. Choosing which tax year a rollover lands in rather than defaulting into one. Sequencing stock sales against a Social Security claiming decision so they do not collide. And covering healthcare if you stop before sixty-five, remembering that whatever generates that income can raise your Medicare premiums later.
Do I need a minimum account size to work with you?
No set minimum. The people I sit with are mostly mid-career and still building, not finished. If anything, the conversations that pay off most are the earlier ones, because there is still time to change the shape of the outcome.
Bradly Stevens, MBA, CEPA™, ChFC®
5405 Morehouse Drive, Suite 245, San Diego, CA 92121
(858) 335-4945
Book a Complimentary Conversation About Your Equity and Your Timeline
No pitch, no obligation to continue afterward. Just a real conversation about what your vested stock is for, what to do with the ESPP position, and what the years either side of your retirement date need to look like.
What happens after you book: You'll get a short intake to share the basics ahead of time, a focused conversation with Brad Stevens (not a call center), and a plain-English summary of anything worth following up on, whether or not you decide to work together.
BAS Financial is not affiliated with, endorsed by, or sponsored by Intuit Inc. Content on this page is educational only and does not constitute personalized investment, tax, or legal advice. Individual circumstances vary, so consult a qualified professional before making decisions about your specific situation.