May is one of the most important months on a retiree’s financial calendar — and the decisions you make (or delay) right now can mean hundreds or even thousands of dollars saved or lost before year-end. April is behind you, taxes are filed, and that means May is your window to review your income picture, confirm your required minimum distributions are on track, check whether your Medicare costs are set to rise next year, and revisit the Social Security timing question if you haven’t claimed yet. Think of this as your mid-spring financial tune-up: low-effort, high-impact.
What financial tasks should retirees tackle in May?
May sits in a sweet spot. The tax deadline pressure has passed, but you still have most of the year ahead to course-correct. Here are the five things worth putting on your May calendar:
Review your 2026 income so far. Add up every taxable source — Social Security, pension, IRA withdrawals, investment income. Knowing where you stand now tells you whether you’re on pace to trigger higher Medicare costs or a bigger tax bill in 2027.
Confirm your RMD schedule. If you’re 73 or older, you must take required minimum distributions (RMDs) from traditional IRAs and most workplace retirement accounts. Missing or under-taking an RMD triggers a 25% penalty on the shortfall — down from 50% after recent law changes, but still painful. If you turned 73 in 2025, your first RMD deadline was April 1, 2026. Going forward, all annual RMDs are due by December 31.
Check your Medicare IRMAA exposure. IRMAA stands for Income-Related Monthly Adjustment Amount — it’s a surcharge added to your Medicare Part B and Part D premiums when your income exceeds certain thresholds. Medicare looks at your tax return from two years prior, so your 2026 Medicare costs are based on your 2024 income. Your 2027 costs, however, will be calculated from your 2025 return — the one you just filed. Now is the perfect time to see if a large withdrawal, Roth conversion, or asset sale last year could push you into a higher bracket.
Revisit your Social Security decision if you haven’t claimed. Every month you delay claiming past your full retirement age (FRA) adds roughly 0.67% to your permanent monthly benefit — that’s 8% per year up to age 70. If you’re between 62 and 70 and still working or drawing down savings, run the numbers one more time.
Top off your emergency cash buffer. Many retirees keep too much in the market and too little in liquid savings. A three-to-six-month cash cushion means you don’t have to sell investments at a bad time just to cover an unexpected bill.
What are the RMD rules for 2025 and 2026?
The SECURE 2.0 Act raised the RMD starting age to 73 for people born between 1951 and 1959, and to 75 for those born in 1960 or later. For 2025 and 2026, if you are 73 or older (and were born before 1960), you must take your RMD every year by December 31. The amount is calculated by dividing your account balance as of December 31 of the prior year by an IRS life-expectancy factor. Your IRA custodian can calculate this for you, but always double-check. Roth IRAs are exempt from RMDs during the original owner’s lifetime — one reason many advisors suggest Roth conversions earlier in retirement.
How do I avoid Medicare IRMAA surcharges?
The Medicare Part B standard premium for 2025 is $185.00 per month. But if your income crosses the first IRMAA threshold — $106,000 for single filers, $212,000 for married couples filing jointly, based on 2023 income — your premium jumps significantly, and it keeps rising in tiers from there. To stay below those thresholds in future years, consider spreading large IRA withdrawals across multiple years rather than taking one big distribution, timing Roth conversions carefully, and being strategic about when you sell appreciated assets. If your income dropped significantly due to a life event like retirement or divorce, you can appeal your IRMAA surcharge using IRS Form SSA-44.
Enjoying this? Subscribe to Silver & Cents — it's free.
When should I claim Social Security to maximise my benefit?
The short answer: the longer you wait (up to age 70), the larger your monthly check. Claiming at 62 permanently reduces your benefit by as much as 30% compared to waiting until your full retirement age. Waiting past FRA earns you delayed retirement credits worth 8% per year. For a married couple, delaying the higher earner’s benefit is especially powerful because the surviving spouse inherits that larger amount. That said, if you have health concerns or genuinely need the income, claiming earlier can still make sense. The break-even point — where total lifetime benefits from waiting surpass those from claiming early — is typically around age 78 to 82.
How much of Social Security is taxable?
Up to 85% of your Social Security benefit can be subject to federal income tax, depending on your “combined income” (adjusted gross income + nontaxable interest + half of your Social Security benefit). If that combined figure is between $25,000 and $34,000 for single filers, up to 50% of benefits may be taxable. Above $34,000, up to 85% is taxable. For married couples filing jointly, the thresholds are $32,000 and $44,000. Note that these thresholds have not been adjusted for inflation since 1983, which means more retirees get caught by them every year. Managing your other income sources — especially IRA withdrawals — is one of the best levers you have to reduce Social Security taxation.
What should I do with my tax return information now that April is over?
Your just-filed 2025 tax return is a financial roadmap. Look at three numbers in particular: your adjusted gross income (AGI), your total taxable income, and how close you came to the next tax bracket. If you have room below the top of the 12% or 22% bracket, May through December is prime time for strategic Roth conversions, harvesting investment gains at favorable rates, or making charitable donations that offset income. These moves are nearly impossible to undo after December 31, but easy to plan now while the year is still young.
Your May Financial Calendar at a Glance
- Now: Review year-to-date income against Medicare IRMAA thresholds
- Now: Confirm your 2026 RMD amount with your IRA custodian
- May–June: Model Roth conversion scenarios with your tax advisor
- Ongoing: Reassess Social Security timing if you haven’t yet claimed
- Before December 31: Complete any planned Roth conversions, RMDs, and charitable gifts
May isn’t a deadline month — it’s a planning month. The retirees who come out ahead financially aren’t the ones who react in December; they’re the ones who set their strategy in spring.
Frequently Asked Questions
Enjoying this? Subscribe to Silver & Cents — it's free.
Frequently Asked Questions
When should I claim Social Security to maximise my benefit?
Waiting until age 70 gives you the largest possible monthly benefit — up to 32% more than claiming at full retirement age, and as much as 77% more than claiming at 62. For married couples, the higher earner should generally delay as long as possible because the surviving spouse will inherit that larger benefit. The typical break-even point where delayed claiming pays off is around age 78 to 82.
How much of my Social Security benefit is taxable?
Between 0% and 85% of your Social Security benefit may be subject to federal income tax, depending on your combined income (AGI plus nontaxable interest plus half your Social Security). Single filers with combined income above $34,000 and married filers above $44,000 will see up to 85% of their benefit taxed. Managing IRA withdrawals and other income sources is the most effective way to reduce this tax exposure.
What are the RMD rules for 2025 and 2026?
Under the SECURE 2.0 Act, required minimum distributions begin at age 73 for those born between 1951 and 1959, and at age 75 for those born in 1960 or later. RMDs must be taken by December 31 each year, and missing one triggers a 25% penalty on the amount you should have withdrawn. Roth IRAs are not subject to RMDs during the original owner’s lifetime.
How do I avoid Medicare IRMAA surcharges?
IRMAA surcharges are triggered when your income from two years prior exceeds $106,000 (single) or $212,000 (married filing jointly), and they can add hundreds of dollars per month to your Medicare Part B and Part D premiums. You can reduce exposure by spreading large IRA withdrawals across multiple years, timing Roth conversions carefully, and managing capital gains. If your income dropped due to retirement or another life event, you can appeal the surcharge using IRS Form SSA-44.
What is the Medicare Part B premium for 2025?
The standard Medicare Part B premium for 2025 is $185.00 per month, up from $174.70 in 2024. Higher-income beneficiaries pay more due to IRMAA surcharges, with the top tier exceeding $620 per month. Most people have their Part B premium deducted automatically from their Social Security benefit each month.