The Roth series · A planning tool · By Rich LoPresti, CFP®
Map your conversion window.
Between your last paycheck and your first required withdrawal there is a stretch of years when income may be lower. Enter a few dates and see where yours is, how long it lasts, and which years come before the usual age-65 Medicare look-back.
What this is. A calendar, not a calculation. It uses only dates: when the paychecks stop, when Social Security starts, when Medicare starts looking at your income, and when the IRS makes you start taking money out. No balances, no tax, no projections. It shows the shape of your window so you can see what claiming earlier or later does to it. Nothing you enter is saved or sent.
Your window.
Year by year.
On a phone, swipe the table sideways to see every column.
| Year | Ages | Paycheck | Social Security | Pension | Medicare look-back | Required withdrawals | Read |
|---|
Medicare look-back: a year's income sets Part B and Part D premiums two years later, so it is marked from the year either of you turns 63. Required withdrawals start at 73 for people born 1951–1959 and 75 for people born 1960 or later. Social Security and pension start years are approximated to the calendar year of the age you chose. Ages shown are the age reached that year.
What claiming later does to the window.
Same dates, three claiming ages for each of you. The number is how many gap years you would have before either Social Security check starts. Each row changes one person's claiming age and holds the other's where you set it, so the window is capped by whichever of you starts first.
| Claim at 62 | Claim at 67 | Claim at 70 |
|---|
Claiming early is not wrong. It is a trade: a check sooner, and a smaller window. Waiting does two things at once: a bigger check for whoever outlives the other, and more years to convert at a low rate. That is why Social Security timing and the conversion plan are one decision, not two.
Bring it back to your plan
What to do with this
- Write down what income will arrive on its own in each gap year: pension, interest, part-time work, rental income. That is what fills the bottom of the bracket before any conversion.
- Decide where the tax money would come from, before deciding how much to convert.
- In Connecticut, remember the state exemption for IRA and pension income phases out between $100,000 and $150,000 of federal AGI for a married couple. Compare the total cost below, within and above that band; do not cross it merely to avoid ending inside it.
- Bring the printout. The years are the easy part; the amounts are the conversation.
What this tool does not show.
Worth being explicit, because a tool like this can imply more than it should.
- No dollars. It does not know your balances, your income, your bracket or your state tax, and it calculates no tax and no savings.
- Dates are approximate. Benefits and withdrawals start in specific months; this works in calendar years. Your own dates may differ by a year at the edges. This calendar supports birth years 1951–1990; earlier RMD start dates need a separate check. Medicare timing assumes enrollment at 65; disability-based coverage and other exceptions can differ.
- It is not a recommendation to convert, or to claim Social Security at any age. Both decisions depend on health, work, spouse's record, and the rest of your plan.
- Rules change. Required withdrawal ages and Medicare rules are shown as they stand in 2026.
The timing
Why the years right after the paychecks stop are often the cheapest time to convert.
Read the article →When the window closes
What required withdrawals look like when the IRA keeps growing.
The freight train →Educational tool written by Rich LoPresti, CFP®. It is not individualized investment, tax or legal advice and not a recommendation. Roth conversions are taxable in the year they occur and cannot be recharacterized. Social Security claiming decisions depend on individual circumstances. Consult a qualified tax advisor. Retirement Approaching provides retirement-planning education. Advisory services are offered through Milestone Asset Management Group, LLC, an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. No investment result or tax savings is guaranteed.