A 61-year-old retiree with a reported $7 million nest egg recently shared advice online for people who are trying to decide when they can finally stop working.
According to the post, the retiree spent decades as a humanities professor, left work at 59, and says retirement has suited him far better than he expected. His story is not useful because everyone can copy his numbers. Most Americans will not retire with anywhere close to $7 million. It is useful because the bigger lesson applies at many wealth levels: retirement is not just a math problem. It is also a lifestyle, identity, and risk-management problem.
His experience points to several practical questions every would-be retiree should ask before walking away from a career for good.
1. Take retirement for a test drive first
Before leaving the workforce permanently, the retiree recommends taking a serious trial run. That could mean a sabbatical, a long leave of absence, or simply a few months where you live as close to your intended retirement lifestyle as possible. The goal is not just to see whether your budget works. It is to see whether you actually like having wide-open days with no job telling you where to be, what to do, or who needs you.
That may sound like the easiest problem in the world, but it is not. Many high earners and high achievers spend decades building an identity around work. Their calendars are full. Their skills are valued. Their colleagues need them. Then retirement arrives, and the structure disappears overnight. For some people, that freedom feels incredible. For others, it feels strangely empty. The professor described retirement as a kind of “unbearable lightness,” borrowing from Milan Kundera’s famous phrase, because total freedom can be more disorienting than people expect.
That is why a test run matters. Use it to answer the emotional questions that spreadsheets cannot. Do you enjoy quiet mornings? Can you fill a weekday without feeling useless? Do you have hobbies, volunteer work, family roles, travel plans, or creative projects that can replace the purpose work used to provide? A retirement plan that only covers money is incomplete. The better plan also answers what your life is going to feel like on a random Tuesday afternoon.
2. Be honest about whether you need structure
One of the best questions to ask yourself is simple: how well do you handle unstructured time? Some people are naturally self-directed. Give them a free day, and they will read, exercise, cook, garden, volunteer, take a class, or start a project. Others struggle when no one else is setting the agenda. That does not mean they should never retire, but it does mean they may need to build more structure into retirement before they leave work.
The retiree in the post seems to fall into the first camp. He filled his days with lap swimming, reading, volunteering, mentoring younger people, and living a mostly television-free routine. That is a very different retirement from simply stopping work and hoping fulfillment appears on its own. His schedule works because it has purpose baked into it. There is movement, learning, service, and connection.
For MIN readers, that may be the most important non-financial takeaway. Retirement does not have to mean doing nothing. In fact, for many people, doing nothing is exactly what makes retirement feel disappointing. A strong retirement plan should include built-in anchors: a morning routine, exercise, social time, family obligations, volunteer commitments, consulting work, travel windows, or recurring projects. Work gives people structure automatically. Retirement requires you to create it yourself.
3. Do not keep working only because you are scared
The retiree says he had around $4 million when he retired and now has around $7 million. In hindsight, he believes he could have retired earlier. That is a familiar problem among financially prepared workers. They hit their number, then keep working anyway because leaving feels too risky, too final, or too unfamiliar.
That fear is understandable. Retirement is one of the few financial decisions where you stop earning first and only find out later whether your plan was strong enough. But there is also a cost to waiting too long. Extra working years may add money to the portfolio, but they also subtract healthy, active years from retirement. For someone whose finances are already secure, the bigger risk may not be running out of money. It may be running out of time.
This is where the numbers matter. If your essential expenses are covered, your portfolio is diversified, your withdrawal rate is reasonable, and your plan has been stress-tested, continuing to work “just in case” may not improve your life very much. Morningstar’s 2025 retirement income research put the safe starting withdrawal rate at 3.9% for retirees seeking steady inflation-adjusted spending over a 30-year retirement with a 90% probability of still having funds remaining at the end. Morningstar also notes that retirees willing to adjust spending over time may be able to start closer to 6%, depending on flexibility and non-portfolio income.
4. Build an income floor before chasing growth
One reason the retiree could stay comfortable after leaving work was that he reportedly built a small guaranteed income floor. In plain English, an income floor is the money that shows up no matter what the stock market does. Social Security is the most common example. A pension can serve the same purpose. Some retirees also use annuities to create additional guaranteed monthly income.
The benefit is psychological as much as financial. If your basic bills are covered by reliable income, you may be able to leave more of your investment portfolio in growth assets without panicking during a downturn. That does not mean everyone should buy an annuity. These products can be complex, irreversible, and expensive if misunderstood. But the basic concept is sound: match dependable income to essential expenses, then let the rest of the portfolio handle long-term growth, inflation protection, and discretionary spending.
Current annuity estimates show why age and product type matter. A representative 2026 SPIA estimate for a 70-year-old man buying a $200,000 life-only immediate annuity is roughly $1,320 to $1,420 per month; for a 70-year-old woman, the estimate is about $1,220 to $1,310 per month. Joint-life options generally pay less because they cover two lives instead of one. Actual quotes vary by insurer, state, payout option, interest rates, and health assumptions, so retirees should compare multiple quotes before committing.
5. Understand what made his portfolio grow
The jump from $4 million to $7 million sounds dramatic, but the timing matters. A retiree who left work around 2021 or 2022 and kept a substantial portion of assets in equities benefited from a very strong market rebound after the difficult 2022 bear market. The S&P 500’s total return was 26.29% in 2023, 25.02% in 2024, and 17.88% in 2025, according to Slickcharts data that separates price return and dividend return.
That kind of sequence can make a retirement plan look brilliant, especially when withdrawals are modest. But it should not be mistaken for a normal expectation every year. The same data show that the S&P 500 lost 18.11% on a total-return basis in 2022. A retiree who hits a bad market early in retirement can face the opposite problem: selling assets while they are down, reducing the portfolio’s ability to recover later.
That is called sequence-of-returns risk, and it is one of the biggest threats to early retirees. The professor’s outcome shows the upside of staying invested through good markets. It should also remind readers to plan for bad ones. Cash reserves, bond ladders, flexible withdrawals, guaranteed income, and a willingness to cut discretionary spending during market downturns can all help protect a retirement plan when the first few years do not go your way.
6. Social Security still matters, even for wealthy retirees
A $7 million retiree may not need Social Security to pay the electric bill, but the benefit still matters because it is inflation-adjusted lifetime income. For most retirees, it matters even more. Social Security is often the foundation of the income floor, and the claiming decision can change the rest of the plan.
For 2026, Social Security beneficiaries are receiving a 2.8% cost-of-living adjustment. The Social Security Administration says the increase is based on the rise in CPI-W from the third quarter of 2024 through the third quarter of 2025. AARP reports that the average retired-worker benefit is expected to rise by about $56, from $2,015 to around $2,071 per month.
That monthly check can reduce the amount a retiree needs to withdraw from savings. Delaying benefits can also increase lifetime income for people who live long enough to benefit from the larger check, although claiming early may make sense for those with health issues, job loss, limited savings, or a need for immediate income. The professor’s larger message still applies: the more reliable income you have covering basic needs, the more flexibility your portfolio has.
7. The real retirement question is not just “Do I have enough?”
The professor’s story is appealing because he appears to have won both sides of retirement: enough money and a lifestyle he genuinely enjoys. But the more useful takeaway is not that everyone needs $7 million. The takeaway is that retirement readiness depends on three layers.
The first layer is financial: Can your portfolio, Social Security, pensions, annuities, and other income sources cover your spending? The second layer is emotional: Are you ready to give up the identity, status, and routine that work provided? The third layer is practical: Have you built a lifestyle that will still feel meaningful after the novelty of not working wears off?
A person with $2 million and modest spending may be more ready than someone with $5 million and no idea what they want their days to look like. A person with a pension and a strong social life may feel more secure than someone with a larger portfolio but no structure. The professor’s experience is a reminder that retirement is not just a finish line. It is a new operating system for your life.
8. Know when enough is enough
There is nothing wrong with working longer because you enjoy your job. There is also nothing wrong with continuing to work because you want a larger cushion, want to support family, or want to leave more money behind. But working longer only because you cannot emotionally accept that you already have enough is a different issue.
That is why “enough” should be defined before the decision gets emotional. Put real numbers around annual spending, taxes, healthcare, housing, travel, long-term care risk, Social Security, and safe withdrawals. Then run the plan through bad markets, higher inflation, and long-life scenarios. If the numbers still work, the question becomes less about money and more about priorities.
The professor’s regret is instructive. He spent extra years working when he believes his portfolio was already sufficient, and those years cannot be reclaimed. Early retirement done well is not about abandoning purpose. It is about choosing where your purpose goes next, whether that means mentoring, volunteering, traveling, creating, helping family, or finally reading the books you never had time to open.
Shutterstock ID: 696138958, Photographer: ElenaR
Editor’s note
This version verifies the S&P 500 total-return figures at approximately 26.29% in 2023, 25.02% in 2024, and 17.88% in 2025. It also updates the Morningstar withdrawal-rate discussion to reflect the 3.9% safe starting withdrawal rate for steady inflation-adjusted spending and notes that flexible strategies may allow higher starting withdrawals. Current 2026 SPIA estimates vary by age, gender, state, insurer, and payout option; a $200,000 life-only SPIA for a 70-year-old is more accurately estimated around $1,220 to $1,420 per month depending on sex and carrier, not a flat $1,500 figure.
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