‘I’m thinking about working part-time as a Lyft driver’: At 58 years old and owning a home valued at $1 million, is it time for me to retire and start enjoying life?

Exploring Retirement Options: A Personal Finance Journey

“Our mortgage rate is 2.5% and we have a $400,000 loan balance.” (Photo subject is a model.) - Getty Images

Letter to Quentin

I am 58 years old, and together with my wife, we have accumulated $1.1 million in our 401(k) accounts and an additional $800,000 invested in stocks. Our home equity stands at $500,000. We currently owe $400,000 on our mortgage, which has a favorable 2.5% interest rate.

Questions on My Mind

• When should I retire? I’m considering leaving my job at 60, while my wife continues teaching for another two years. We would then rely on the Affordable Care Act for health coverage until we reach 65. During the five years after I retire, I could gradually convert my 401(k) to a Roth IRA to help reduce future required minimum distributions.
• Should we relocate? Selling our home in a high-tax state and moving to a state with no income tax could make Roth conversions more tax-efficient.
• Is it time to sell our house? Our property is in a desirable neighborhood and is valued at around $1 million. However, I’m concerned that advances in artificial intelligence could make expensive homes less affordable in the future. Should we sell now and use the proceeds to support ourselves between ages 60 and 65?
• Retirement lifestyle: I plan to claim Social Security at 70, and my wife will receive a modest pension. Between 60 and 70, I want to prioritize my health and enjoy life rather than continue working.

Immediate Plans

We’re thinking of selling our house next year and moving into a smaller apartment in a state without income tax. I’d like to stop working at the beginning of 2027. Our income would come from my wife’s teaching job and possibly the proceeds from our home sale. I’m also considering driving for Lyft part-time, which could bring in about $30,000 annually and offers flexibility. Health insurance would be provided through my wife’s employer, though her job is demanding. I’m interested in focusing more on options trading after retiring from my main job.

Our general approach is for one of us to keep working. If necessary, I could take a less demanding job to maintain health coverage, or my wife could continue working. We haven’t finalized this yet. I also want to dedicate more time to improving my health and diet. I don’t have extravagant tastes and value having the freedom to think independently. I’m reaching a stage where I’d prefer not to own many assets.

Work has become increasingly stressful, and my health and nutrition have suffered as a result. Both our parents are elderly, so I need to plan for potentially another 30 years.

Popular Reads from MarketWatch

Weighing the Options

Don’t miss:

You may be trading one set of challenges—job stress, poor diet, and lack of free time—for a new set of issues. - MarketWatch illustration

Response: Dear Options

Your finances are in excellent shape, but you mention wanting to improve your physical health. Professionally, you seem dissatisfied. While you haven’t specified your occupation, your wife’s teaching career is clearly stressful. Any decision to retire or move will impact both of you, so it’s important to make these choices together to ensure a fulfilling retirement for both partners.

Be cautious about exchanging one group of problems—such as job stress and unhealthy habits—for another, like the demands of part-time work, higher healthcare costs, or imbalances in how each spouse spends their time. Chronic work stress is a real concern and should be addressed regardless of your retirement plans.

You’re planning to use the Affordable Care Act for health insurance. If Congress doesn’t extend enhanced tax credits, ACA premiums could more than double to about $1,900 per year for subsidized enrollees. Those earning over 400% of the federal poverty level could lose eligibility for these credits if they expire. According to , delays in Congressional action have already led to higher premiums and forced some to drop coverage.

Health, Work, and Lifestyle

A major reason you want to retire early is to focus on your health and nutrition. While having more free time can help, you don’t have to wait for retirement to start making positive changes. At 58, investing time in exercise and healthy habits is especially valuable. Simply having more free days may not automatically lead to better health.

Your idea of driving for Lyft as a source of extra income is practical, but keep in mind that it’s a sedentary job with no guaranteed earnings. You’ll also be responsible for vehicle upkeep and insurance, and you may only keep 70% of fares. For supplemental income, though, it’s a reasonable option.

Delaying Social Security until age 70 is a smart move, as your benefit is calculated based on your 35 highest-earning years. In 2025, the maximum taxable earnings for Social Security is $176,100, with the highest monthly benefit at $5,108 for those who wait until 70. Claiming at 62 would reduce this to $2,831 per month.

Planning for Retirement Income

Your life expectancy is a key factor in deciding when to claim Social Security. Health issues later in life could make waiting less advantageous, but Social Security’s annual cost-of-living adjustments help protect against inflation, making delayed claiming attractive for many.

You’ve secured a great mortgage rate and have nearly $2 million saved for retirement. Withdrawing 4% annually from your 401(k) between ages 60 and 70 would provide about $44,000 per year before taxes. Assuming a 5% annual return after inflation, you’d still have $1.2 million left after 10 years.

Be mindful not to convert too much to a Roth IRA in a single year, as this could push you into a higher tax bracket and reduce your ACA premium tax credits. Your strategy to manage annual Roth conversions and keep your income within certain limits is wise, as it helps control taxes and maximize insurance subsidies until you qualify for Medicare.

Relocating to a state without income tax and executing a 401(k) Roth conversion ladder are both smart financial moves. Lowering your expenses by downsizing and moving to a more affordable area can further strengthen your retirement plan. Just be sure you’re not making irreversible decisions in haste.

Concerns about artificial intelligence impacting the housing market are unlikely to significantly affect your retirement outlook.

Further Reading

Most Read from MarketWatch