The Roth conversion window
Between retirement (or part-year retirement) and age 73 when RMDs start, you may have the lowest income of your adult life. Filling up to the top of the 12% or 22% bracket each year with Roth conversions can save substantial tax later. Every dollar converted at a low rate is a dollar that won't come out later at RMD-inflated rates, and the conversion also shrinks the future RMDs themselves. Conversions can't be undone after year-end, so the amount is worth calculating rather than guessing.
How Social Security gets taxed
Depending on your other income, up to 85% of Social Security benefits become taxable, on a sliding formula driven by 'provisional income.' Florida doesn't tax benefits (or anything else on the personal side), but the federal formula means IRA withdrawals and conversions can drag benefits into taxable territory alongside them. The 2025 legislation also added a temporary extra deduction for taxpayers 65 and older, in effect for 2025 through 2028, which softens the picture for many retirees in these exact years.
IRMAA awareness
Medicare Part B and D premiums increase with income (IRMAA). Roth conversions and large retirement account distributions can push you into higher IRMAA tiers. Planning around the brackets matters. IRMAA works on a two-year lookback: this year's modified AGI sets the premium two years out, and the tiers are cliffs. A conversion that overshoots a tier boundary by one dollar raises both spouses' premiums for a full year.
Replacing your withholding
Paychecks withheld tax automatically; retirement income doesn't unless you make it. Pension and IRA payers withhold on request (W-4P), Social Security withholds on request (W-4V), and the alternative is quarterly estimated payments. A useful quirk: withholding from an IRA distribution late in the year is treated as paid evenly through the year, which can cure an estimated-payment shortfall in December.
The order you spend accounts matters
Conventional sequencing spends taxable accounts first, tax-deferred second, Roth last, letting the tax-free bucket compound longest. The better answer is usually blended: enough deferred-account withdrawals or conversions each year to use up the low brackets, capital gains harvested at the 0% rate where income allows, and Roth kept for spikes and late-life expenses. The wrong sequence quietly costs five figures over a retirement; the right one is just arithmetic done annually.
Common questions
- When should I start Social Security?
- Not strictly a tax question. Delaying increases the benefit but defers income. We model the tax side; you should also get a financial advisor's view on the longevity side.
- Is Social Security taxed in Florida?
- Florida has no personal income tax, so no. Federally, up to 85% of benefits can be taxable depending on your other income.
- Do I still need to file a return after I retire?
- Usually yes. IRA distributions, pensions, taxable Social Security, and investment income keep most retirees over the filing threshold, and filing is how conversion and withholding strategies get executed.
- I retired mid-year with a high salary through June. Should I convert this year?
- Probably wait. Conversions price at your marginal rate, and a half-year of salary usually keeps that rate high. The first full calendar year without wages is typically when the window truly opens.
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