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The classic retirement picture is a cake in the break room, a gold watch, and a hard stop on Friday.
I have never met a founder who wants that. We built something because we like building. The question is not how to stop. It is how to make work a choice instead of a requirement, and how to do it without tripping over the rules that were written for people with a Friday finish.
Why does the stop-date model fail for founders?
Because it was designed around an employer with a retirement date and a pension that starts on it. A founder has neither.
Look at the labor data. In 2025, 19.1 percent of people age 65 and older participated in the labor force. That was down from a recent peak of 20.2 percent in 2019 and still well above the 12.9 percent of 2000.1
Working past 65 is not unusual anymore. What matters is whether you do it because you have to or because you want to. Those are two different retirements.
Retire from, or retire to?
Most advice asks what you are retiring from. I think the better question is what you are retiring to. If you cannot answer that, you are not planning a retirement. You are planning an absence.
Ben Felix, a Chief Investment Officer at PWL Capital, reviewed the research on money and well-being in a video posted on May 3, 2026.7
Choosing time over money is generally a good decision.
For a founder who can set their own hours, that is a design choice, not a luxury.
| Stop-date retirement | Work-optional design |
|---|---|
| One finish line | A slope you can steer |
| Income ends abruptly | Income tapers by choice |
| Identity ends with the job | Identity shifts to chosen projects |
| Success is leaving | Success is options |
What does "work optional" actually mean?
It means your essential expenses are covered by income that does not depend on you showing up. Anything you earn beyond that is a bonus you choose.
Do the math in two columns. In one, write the yearly cost of the life you need: housing, food, health coverage, taxes, insurance. In the other, list reliable income that arrives without your daily effort: Social Security, any pension, withdrawals from accounts you have built, and income from assets you own, not just from effort.
If the second column covers the first, work is optional. If it covers half, you know exactly how much work is still required. Either answer is useful, because now you have a number instead of a fear.
My own rule has been to stay liquid. I have never taken a loan for the business or used a credit card for business needs. A cash cushion is what makes a taper possible, because it lets you say no to a deal you do not want.
How do you taper a business instead of quitting it?
You design the hand-off years before you want it. The sequence below is a framework, not a promise of how any business goes. Your pace will differ.
- SystemizeWrite down how the work gets done
- DelegateMove repeat tasks to people or tools
- NarrowFewer offers, fewer clients
- Cut hoursSet your weekly work cap
- AdviseMove from operator to owner
- ChooseEach year, decide what stays
I stopped having employees in 2024, and I run lean on purpose. Whatever shape your business takes, the principle holds: every task you write down is a task you can later hand off, and every offer you drop is a day you get back. A weekly review keeps that list from rotting, and the post on discipline and freedom explains why I build walls around the things I care about.
Start the taper before you need it
Tapering in a hurry because of health or burnout costs you bargaining power on every decision. Taper from strength and you pick the terms.
What does Social Security do if you keep earning?
Social Security allows you to work while collecting benefits, with an earnings limit before full retirement age. Full retirement age is 67 for people born in 1960 or later.3
The 2026 rules
- Under full retirement age all year: Social Security deducts $1 from benefits for each $2 you earn above $24,480.
- The year you reach full retirement age: $1 is deducted for every $3 you earn above $65,160, and only earnings before the month you reach full retirement age count.
- After full retirement age: no limit on earnings.2
For self-employed people, Social Security counts net earnings from self-employment, not gross revenue, and generally counts income when you receive it, not when you earn it.2 If benefits are withheld because of your work, your monthly benefit is recalculated upward when you reach full retirement age to account for those months.2
Claiming age is its own decision
Claiming as early as 62 means a permanently smaller benefit. For the 1960-and-later group, SSA's table shows a worker who starts at 62 receiving 70 percent of the full benefit, and each full year you delay past full retirement age adds 8 percent, up to age 70.3 Whether to claim early, at full retirement age or later depends on your health, other income and household. That is a decision to model with a professional and SSA's own tools, not a rule of thumb from a blog.
What do Medicare and required withdrawals mean if you keep working?
Do you need to sign up for Medicare?
You need to check, not assume. Medicare's Initial Enrollment Period lasts seven months, beginning three months before the month you turn 65 and ending three months after. If you miss it, you may have to wait to sign up and pay a monthly late enrollment penalty for as long as you have Part B coverage, and the penalty goes up the longer you wait.4
Self-employed people often do not have employer coverage, which is the situation where timing matters most. Read Medicare's own guidance for people who are working, and ask a licensed advisor about your specific coverage before you decide to wait.
What happens to required withdrawals?
The IRS says you generally must start withdrawals from traditional IRAs, SEP IRAs, SIMPLE IRAs and retirement plan accounts at age 73. Participants in a workplace plan can delay until the year they retire, unless they are a 5% owner of the business sponsoring the plan.5
Read that last clause twice. As the owner of a solo business that sponsors your own plan, you are the owner. The still-working delay is not a safe assumption for you.
The IRS also states that withdrawals from Roth IRAs and designated Roth accounts are not required until after the death of the account owner.5 That is one reason people compare Roth and traditional accounts, as in the Roth IRA basics. It is not a reason to choose one without seeing your tax picture.
I am not trying to retire from my life's work. I am trying to make sure no one else decides when I stop.
How do you pay for the bridge years?
Most tapers begin before any benefit does. If you cut back at 55 or 58, there is a gap before Social Security, before Medicare and before ordinary retirement account withdrawals are easy. I call those the bridge years, and they are where good plans quietly fail.
The IRS says that withdrawals from an IRA or retirement plan before age 59 and a half are generally "early" distributions, and that a 10% additional tax applies on the taxable part unless an exception applies.6 That does not mean never touch the accounts. It means the bridge needs its own funding, designed in advance, so you are not forced to pick between a penalty and a cut in lifestyle.
Three questions will shape the bridge, and none has a one-size answer:
- How many months of essential costs can you cover from cash and ordinary savings, outside retirement accounts?
- What income from the business, even a smaller taper income, is realistic to keep for those years?
- Which accounts carry penalties for early use, and which exceptions might apply to you? Ask a tax professional before you rely on one.
Think of the bridge as a project with a budget and a start date. It is the same discipline as a launch plan, applied to your own life. The cash buffer guide is the first plank.
What gives your days a shape?
Money covers the floor. Shape covers the rest, and shape is where founders get lost. A week with no structure is not freedom. It is drift with better weather.
Design three things before the taper begins:
- A weekly rhythm. Two or three anchors a week: a morning routine, a standing meeting, a day for deep work or study.
- A body of work you choose. Not "keep the business going" but a specific project you would do for free: writing, mentoring, building something small.
- A circle. People who are not in your business. Retirement is lonely for the person whose identity was the company.
- A health baseline. Strength, sleep and checkups on a schedule, not when something breaks.
- A yearly review. Each January, re-ask: what stays, what goes, what is new?
Hobbies deserve their own treatment, and I will write about them separately. For now, notice this: the best retirement plans I see are built around something people are moving toward, not away from.
What should you do this quarter?
Small moves, in order.
- Write the two-column test and keep it where you can see it.
- Pick one task or offer to document or drop. Start the taper with one item.
- Check your own Social Security record and statement at ssa.gov so you know your actual numbers, not the average.
- Mark your Medicare window on a calendar if you are within a few years of 65.
- Ask your plan provider about withdrawal rules for each account type you hold.
My grandmother asked me one question that changed my view of all of this, and the full story is here. She did not ask when I would stop. She asked what the plan was.
That is the question that matters for founders too. Build a plan where work is a choice, and you can keep building for as long as you love it.
More guides are in the Investing and Retirement hub.
Educational content, not financial, tax, legal or investment advice. Talk to a licensed professional about your situation.
Keep building.Ekai
Questions people ask
Can I keep working while collecting Social Security?
Yes. In 2026, if you are under full retirement age all year, Social Security withholds $1 for every $2 you earn above $24,480. In the year you reach full retirement age the limit is $65,160 with $1 withheld for every $3 above it, counting only earnings before your birthday month. After full retirement age there is no limit on earnings.
What is the full retirement age for people born in 1960 or later?
67. Claiming as early as 62 gives a permanently smaller monthly benefit, and each full year you delay past full retirement age adds 8%, up to age 70.
When do I have to sign up for Medicare?
Your Initial Enrollment Period lasts seven months: it starts three months before the month you turn 65 and ends three months after. Miss it and you may pay a late enrollment penalty for as long as you have Part B, so check your own coverage situation.
Do I have to take required minimum distributions if I am still working?
Workplace plan participants can often delay until they retire, but not if they own 5% or more of the business sponsoring the plan. Traditional IRAs and SEP IRAs generally require withdrawals starting at 73. Roth IRAs do not require withdrawals during the owner's lifetime.
Sources
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