MW 'I'm considering driving Lyft part time': I'm 58 with a $1 million home. Do I finally give up work and enjoy life?
By Quentin Fottrell
'One thought is for me to stop working at age 60, while my wife continues for two more years at her teaching job'
"Our mortgage rate is 2.5% and we have a $400,000 loan balance." (Photo subject is a model.)
Dear Quentin,
I am 58. My wife and I have a combined 401(k) balance of $1.1 million and $800,000 in stocks. We also have $500,000 in home equity. Our mortgage rate is 2.5% and we have a $400,000 loan balance.
A few things have been playing on my mind:
1. When is a good time to stop working? One thought is for me to stop at age 60, while my wife continues for two more years at her teaching job. Then we move to the Affordable Care Act for health insurance until we turn 65. During the five-year period after I retire, I can convert my 401(k) to a Roth to the extent that I can in order to lower my required minimum distributions down the line.
2. If we sell our home in a high-tax state and move to a no-income-tax state, that would help with my Roth conversion.
3. Our home is in a very good area and has an estimated value of $1 million. However, I worry that with the growth of artificial intelligence, not many people will be able to afford expensive homes in the future. In that case, should we consider selling it now and using the proceeds to fund our living expenses from ages 60 to 65?
4. I plan to take Social Security at 70, and my wife will also get a modest pension. Between ages 60 and 70, I want to focus not on work, but on enjoying my health and vitality while I still have it.
Here is my immediate plan:
Sell the home next year and downsize to an apartment in a no-income-tax state. Stop working at the start of 2027. Our sources of income would be my wife's teaching job and potentially money from the sale of our home. I'm considering driving Lyft $(LYFT)$ part time, which might bring in $30,000 a year. I like the flexibility of it. We would have health insurance through my wife's work. Her job is quite stressful, with all the grading and multiple classes. I also like trading options and want to focus on that after I finish working.
Overall, the idea is that one of us works. If I have to work, I have to downsize to a lower-scale job for health insurance, or else my wife will keep working. We haven't finalized that part yet. That also gives me the chance to work on my health and diet. I have no lavish interests. I want to have a life where I can think for myself. I'm getting to a point where I don't want to own anything from an asset perspective.
Work, of course, is very stressful and I've been neglecting my health and diet somewhat. Both our parents are quite elderly and therefore, in theory, I need to plan for about 30 more years.
Weighing Options
You can email The Moneyist with any financial and ethical questions at qfottrell@marketwatch.com, and follow Quentin Fottrell on X, the platform formerly known as Twitter.
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You're potentially swapping one set of problems - a stressful job, a bad diet, lack of free time and exercise - for an entirely new set of problems.
Dear Options,
Financially, you're in great shape.
Physically, you say you need to be in better shape.
Professionally, you're bent out of shape.
You don't say what you do for a living. Your wife is a teacher, and you say (rightly so) that her job is extremely stressful. Assuming you're both of similar age, your decision to stop working and move to a different state will affect your wife, whether or not she chooses to give up her own job. This is obviously a decision that affects both of you, and it should be made with mutual agreement. Otherwise, it could be a very long retirement.
Beware of swapping one set of problems - a stressful job, a bad diet, lack of free time and exercise - for an entirely new set of problems. The new problems, in no particular order, might include: tiring or stressful part-time work; increased healthcare costs; and one spouse taking their foot off the gas for the luxury (and burden) of more free time while the other spouse continues working. That said, chronic work-related stress is real. You need to deal with that no matter what else you decide to do.
You're also planning to eventually move to the Affordable Care Act marketplace. Without an extension of the tax credits by Congress, premiums for the ACA are projected to more than double to roughly $1,900 a year per subsidized enrollee, says the health-research organization KFF. People earning more than 400% above the federal poverty level who currently receive tax credits could lose their eligibility for tax credits altogether if these enhanced credits expire.
"Congress is expected to vote on whether to extend the enhanced premium tax credit $(PTC)$ individuals and families receive when they enroll in coverage through the Affordable Care Act marketplaces," according to the journal Health Affairs. "Congress's failure to act sooner has already increased premiums and forced many consumers to make the tough decision to drop coverage based on the expectation of lower or no PTC."
Health, work and diet
One significant part of your wish to retire early is to spend more time focusing on your diet and health. You will have more time to do this if you're not working, but working does not preclude you from addressing this and, at 58, the more time you spend building cardio and muscle strength, the better. I'm not convinced that being given a free day every day will be the answer to that problem.
You plan to give up your job and, to make ends meet during your semi-retirement, perhaps become a Lyft driver. It's good that this is an option for discretionary income, rather than a necessity. It's a sedentary job, and it comes with no guarantees. You could drive around for hours waiting for a pickup. You are also responsible for your car's maintenance and insurance, and you could end up with just 70% of your clients' fare. For pocket money, however, it's A-OK.
Given your expected longevity, you're smart to wait to claim Social Security. Your benefit is based on your 35 highest-earning years. For 2025, the maximum earnings on which a worker pays into Social Security is $176,100, and the maximum possible monthly Social Security benefit is $5,108 for someone who waits until age 70 to claim. Someone with that same benefit who claims at 62 in 2025 would receive $2,831 a month.
Retirement income
Your longevity is key to whether you wait to claim. You may encounter health issues as you age that could make waiting to claim Social Security less beneficial. Inflation is one of the biggest challenges for many retired people. Given the added benefit of Social Security's annual cost-of-living-adjustment, known as the COLA, waiting to claim your benefits may also help protect you against inflation.
The good news: You have an amazing interest rate on your home. You have a substantial sum of money saved for retirement - nearly $2 million, including your 401(k) and other stocks. If you took 4% just from your 401(k) over the 10-year period from retirement at age 60 to claiming Social Security at age 70, you would have an income of $44,000 a year before tax ($440,000 in total). And with a 5% annual return on your 401(k) after inflation, at the end of those 10 years you'd still have $1.2 million in your account.
Converting too much to a Roth in one year can raise your income, push you into a higher tax bracket and reduce - or even eliminate - your ACA premium tax credits. Your plan, and it's a good one, is to keep a lid on your income tax and maximize your insurance subsidies. By planning annual Roth conversions and staying within your income thresholds, you should be able to manage your ACA premiums until you apply for Medicare.
Overall, moving to a state without income tax and carrying out a 401(k) Roth ladder conversion are savvy plans. The more you can reduce your costs, the better. Why live in a big house when you can downsize in a state with a lower cost of living? This is the time to start planning. I just want you to be sure that you're not going to rush into early retirement only to discover you have made decisions that will be difficult to reverse later on.
Practically speaking, the issues AI will raise shouldn't affect your retirement plan.
Related: 'Where are we vulnerable?' My husband and I are in our 50s. Our $450K mortgage is paid off. We have $500K in IRAs.
The Moneyist regrets he cannot reply to questions individually.
More columns from Quentin Fottrell:
'We all have economic jitters': After the Fed cut rates, should my son buy a $600K house?
'The stress at my job is getting worse every day': I'm 61, earn $177K, and have a 401(k) with $965K. Do I retire and downsize?
'It's a perilous choice': I've been offered a part-time job. Do I file for Social Security at 67 or 70?
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-Quentin Fottrell
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January 18, 2026 08:53 ET (13:53 GMT)
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