I Asked ChatGPT What the Smartest Retirement Moves Are for People in Their 50s

Your 50s are when retirement planning stops being something you’ll deal with “someday” and becomes something you need to handle right now. I asked ChatGPT what the smartest moves are for people in this decade, when you still have time to make changes but not unlimited time.

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The AI’s response was thorough and practical, covering everything from catch-up contributions to estate planning. Here’s what ChatGPT said people in their 50s should focus on to set themselves up for a comfortable retirement.

ChatGPT started with the most obvious advantage people in their 50s have — the ability to contribute extra money to retirement accounts.

The AI explained that in 2025, people 50 and older can contribute up to $31,000 to their 401(k), which includes a $7,500 catch-up contribution. For IRAs, catch-up contributions allow an extra $1,000 annually for a total of $8,000.

ChatGPT made the point that these catch-up contributions matter more in your 50s because you have less time for compound growth to work its magic. Every dollar you can squeeze into tax-advantaged accounts now will have a bigger impact than waiting even a few more years.

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The AI spent considerable time on healthcare planning, which makes sense since medical costs are often the biggest wild card in retirement budgets.

ChatGPT recommended researching Medicare options before turning 65, even though that might seem early. Understanding how Medicare works takes time, and you’ll want to know your options well before you need to make decisions.

If you’re eligible for a health savings account, the AI called it “triple tax-advantaged.” That means, you get a deduction when you contribute, the money grows tax-free and you can withdraw it tax-free for medical expenses.

ChatGPT also suggested looking into long-term care insurance while you’re still healthy and employed. Waiting until you have health problems makes coverage much more expensive or impossible to get.

ChatGPT wants you to enter retirement completely debt-free, and it was especially focused on paying off your mortgage.

The AI recommended prioritizing credit card debt and other high-interest obligations first, which makes mathematical sense. But it also acknowledged the debate about whether to pay off low-interest debt versus investing the money instead.

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Going into retirement without a mortgage payment dramatically reduces the income you’ll need from your savings and Social Security.

The AI addressed the tricky question of how to adjust your investment mix as you get closer to retirement.

ChatGPT recommended gradually shifting from aggressive growth to more balanced allocations but warned against becoming too conservative too quickly. The AI pointed out that you might have 30 or more years in retirement, so you still need some growth investments.

Target-date funds got a mention as an option that automatically adjusts as you age. The AI also recommended reviewing and rebalancing your portfolio annually to keep things on track.

ChatGPT recognized that your 50s are typically your highest-earning years and advised using this to your advantage.

The AI recommended saving aggressively during this decade since you’ll probably never earn more than you do right now. If you’re behind on retirement savings, ChatGPT suggested considering working a few extra years to catch up.

The AI also mentioned exploring part-time or consulting work as a bridge to full retirement.

Housing was one of the first things ChatGPT brought up. As housing is most people’s largest expense, it’s an important one to think about.

The AI suggested downsizing or relocating to a lower-cost area. But it went beyond just thinking about purchase prices to include property taxes, maintenance costs and proximity to healthcare.

ChatGPT raised the question of whether you want to age in place or eventually move to a retirement community. Making this decision in your 50s gives you time to plan rather than being forced into choices later.

The AI spent time on Social Security timing, which can make a huge difference in your retirement income.

ChatGPT recommended understanding how working longer affects your benefits and considering delaying benefits until age 70 for maximum monthly payments. The AI also mentioned factoring in spousal benefits and survivor benefits.

Reviewing your Social Security statement annually made the AI’s list to make sure your earnings history is accurate and to get updated benefit projections.

ChatGPT didn’t ignore the less fun aspects of retirement planning like estate planning documents.

The AI recommended creating or updating your will, power of attorney and healthcare directives. For some people, trust structures might make sense too.

ChatGPT advised reviewing and updating beneficiaries on all accounts, which is easy to forget but important. The AI also mentioned planning for potential incapacity with proper legal documents.

Rather than just focusing on accumulating money, ChatGPT addressed how you’ll actually use your savings in retirement.

The AI recommended planning how you’ll generate income from various sources and considering the tax implications of different withdrawal strategies. Thinking about which accounts to tap first — taxable versus tax-deferred — can save significant money over time.

ChatGPT mentioned planning for required minimum distributions starting at age 73, which will force you to withdraw money from traditional retirement accounts whether you need want to or not.

ChatGPT suggested considering a fee-only financial planner, getting professional tax planning advice, reviewing insurance needs and potentially working with an estate planning attorney.

It wrote about the complexity of financial planning increases significantly in your 50s, making professional guidance more valuable than it might have been earlier in your career.

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