ChatGPT’s Top 5 Money Moves Every Retiree Should Make Now
Written by
Jordan Rosenfeld
Edited by
Brendan McGinley
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You may have more leisure in retirement, but that doesn’t mean you should put your finances on autopilot. With costs increasing, tax rules changing and withdrawal deadlines threatening to ding your income, a few smart tweaks now can protect more of what you’ve saved.
GOBankingRates asked ChatGPT for the top five money moves every retiree should make now. Here’s where to focus most immediately.
1. Optimize Medicare During Fall Open Enrollment
Healthcare is pricey, even with government coverage. Compare your current plan’s costs, networks and drug coverage against alternatives because prices and formularies change each year, the AI said. Part B’s standard premium has now increased to $185 per month, however Part D caps annual out-of-pocket drug costs at $2,000.
Open Enrollment runs Oct. 15 to Dec. 7. Use Medicare Plan Finder to price your medications and check which plan better fits your doctors and travel needs. If your 2023 income triggers IRMAA (Income-Related Monthly Adjustment Amount) surcharges, you may be able to appeal with Form SSA-44.
Quick tip: Verify every medication’s tier and prior authorization rules before switching.
2. Lock In a Smart 2025 Tax Plan
Plan your brackets deliberately, ChatGPT said. Consider partial Roth conversions, harvesting gains in low brackets and a tax-efficient withdrawal sequence in an order that makes sense (generally taxable, then tax-deferred, then Roth) to manage lifetime taxes, IRMAA and the taxation of Social Security. Remember that some Tax Cuts and Jobs Act provisions sunset after 2025 and changes tied to the One Big Beautiful Bill Act may also affect deductions and brackets.
Quick tip: Estimate your 2025 taxes and convert just enough to Roth to stay within your current bracket.
3. Take the Right RMDs — On Time and Tax-Smart
Required minimum distributions (RMDs) begin at age 73. If you turned 73 this year, be sure you take the correct amount to avoid penalties. The AI recommended coordinating withdrawals with your tax plan and to consider using IRA withholding to cover taxes evenly through the year. If you’re 70 1/2 or older, qualified charitable distributions can count toward your IRA RMD and keep taxable income lower.
Quick tip: Put custodian RMD deadlines on your calendar now and confirm each account’s calculation.
4. Build a Cash Bucket and Rebalance
Keep roughly one to two years of planned withdrawals in cash-like reserves so you aren’t forced to sell during a downturn, ChatGPT said. Rebalance the rest of your portfolio to your target mix to control risk and reduce sequence-of-returns damage — in other words, remember that your investing risks have changed at this stage of your life.
Quick tip: Refill the cash bucket for 2026 to 2027 spending then rebalance in tax-aware fashion.
5. Update Beneficiaries and Essential Estate Docs
Beneficiary designations on IRAs, 401(k) plans, life insurance and bank accounts override your will, so review them yearly and after any life change. Also refresh your will, financial power of attorney and advance healthcare directive using state-specific forms. Don’t forget about other assets either, such as real estate, art or collectibles.
Quick tip: Confirm both primary and contingent beneficiaries on every account and keep copies with your key documents.
Your plan doesn’t have to be perfect; it just has to be current — make these updates now and give your future self a raise.
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