When it comes to retirement planning, everyone has an opinion. Financial advisors push complicated portfolios, bloggers swear by extreme savings and your neighbor won’t stop talking about their real estate investment.
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So I decided to cut through the noise and ask ChatGPT directly: What’s the single smartest retirement move to make in 2026?
The answer was surprisingly straightforward – and it has everything to do with timing.
ChatGPT’s response was clear: maximize your tax-advantaged accounts with a Roth-first strategy while tax rates are still low.
This means prioritizing Roth IRA contributions, Roth 401(k) contributions and Roth conversions over traditional pre-tax retirement accounts. The reason it is so important is that it comes down to a major deadline.
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Provisions of the Tax Cuts and Jobs Act expire after 2025. That means many Americans will face higher federal tax rates starting in 2026 and beyond.
If you converted money from a traditional IRA to a Roth IRA before rates went up, you pay taxes at today’s lower rates. Then that money is tax-free forever and you never pay tax again—even when rates are higher.
ChatGPT said it created a perfect opportunity. Lock in lower tax rates now to move money into Roth accounts before the window closes. For people who expect to be in the same or higher tax bracket in retirement, this move can save thousands of dollars over a lifetime.
The Roth-first strategy is not complicated, but it requires action in three areas.
First, contribute to a Roth IRA or Roth 401(k) instead of the traditional versions. If your income is too high for direct Roth IRA contributions, you can use a backdoor Roth strategy by contributing to a traditional IRA and immediately converting it.
Second, consider converting your existing traditional IRA money to a Roth. You will pay tax on the conversion amount this year, but then the money is tax-free. The key is to convert when your income is low or tax rates are favorable — which 2025 and early 2026 likely represent before rates rise.
Third, if you have a 401(k) with Roth options, funnel as much as possible to the Roth side. For 2025, the 401(k) contribution limit is $23,000 for people under 50 and $30,500 for those 50 and older.
