I Asked ChatGPT the Smartest Retirement Move To Make in 2026 — Its Advice Was Shockingly Simple
Written by
Laura Beck
Edited by
Molly Sullivan
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When it comes to retirement planning, everyone’s got an opinion. Financial advisors push complicated portfolios, bloggers swear by extreme savings and your neighbor won’t stop talking about their real estate investments.
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.
The Answer: Go All-In on Roth Accounts
ChatGPT’s response was clear: Maximize your tax-advantaged accounts with a Roth-first strategy while tax rates are still relatively low.
That means prioritizing Roth IRA contributions, Roth 401(k) contributions and Roth conversions over traditional pretax retirement accounts. The reason this matters so much right now comes down to one major deadline.
Why 2026 Is a Critical Year
The Tax Cuts and Jobs Act provisions expire after 2025. That means many Americans will face higher federal tax rates starting in 2026 and beyond.
If you convert money from a traditional IRA to a Roth IRA before rates go up, you pay taxes at today’s lower rates. Then that money grows tax-free forever and you never pay taxes on it again — even when rates are higher.
ChatGPT explained that this creates a perfect opportunity. Lock in lower tax rates now by moving money into Roth accounts before the window closes. For people who expect to be in a similar or higher tax bracket in retirement, this move could save thousands of dollars over a lifetime.
How To Actually Do This
The Roth-first strategy isn’t 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 the backdoor Roth strategy by contributing to a traditional IRA and immediately converting it.
Second, consider converting some of your existing traditional IRA money to a Roth. You’ll pay taxes on the conversion amount this year, but then that money grows tax-free. The key is converting when your income is lower or tax rates are favorable — which is exactly what 2025 and early 2026 represent before rates potentially rise.
Third, if you have a 401(k) with Roth options, funnel as much as possible into 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.
The Math Makes Sense
Here’s a simple example. Say you convert $50,000 from a traditional IRA to a Roth while you’re in the 22% tax bracket. You pay $11,000 in taxes now.
But if tax rates rise to 25% or higher in retirement and you would have withdrawn that same $50,000 then, you’d pay $12,500 or more. Plus, all the growth on that $50,000 stays completely tax-free in the Roth account.
The longer that money has to grow, the more valuable the tax-free status becomes. For someone in their 40s or 50s, this could mean tens of thousands of dollars in tax savings over a 30-year retirement.
Other Smart Moves ChatGPT Mentioned
While the Roth strategy was the standout recommendation, ChatGPT also highlighted a few other moves worth considering in 2026.
Delay claiming Social Security if possible. Every year you wait between your full retirement age and 70 increases your benefit by about 8%. For most people, that higher lifetime payout is worth the wait.
Build up cash reserves. Having one to two years of essential expenses in cash means you won’t be forced to sell investments during a market downturn. This bucket strategy protects your portfolio during rough patches.
Cut housing costs. Whether that means refinancing if rates drop, downsizing before demand spikes or moving to a lower-cost area, getting your housing situation settled now can save thousands annually in retirement.
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