Author: Hazel Secco, CFP®, CDFA®
Estimated reading time: 8 minutes
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Table of contents
- The Roth Conversion Window in Early Retirement
- Why a Roth Conversion Before RMDs Is Use-It-or-Lose-It
- Three Ways High Earners Miss the Window
- Missing the Window Compounds Into the Widow’s Penalty
- Why Using the Window Feels Wrong (and Why That’s the Trap)
- What to Do This Week
- Want the full framework?
- Listen to This Episode
- Frequently Asked Questions
- Sources
For most of your working life, your top dollars have been taxed at 32, 35, even 37 percent. Then you retire, the paycheck stops, and for a few short years your bracket can drop to 22 percent, sometimes even 12. That stretch is the Roth conversion window: for many people, five to ten years in early retirement when you can move six figures from pre-tax retirement accounts into a tax-free Roth at some of the lowest rates you will ever see.
Here’s what I keep seeing in my practice: the people most likely to walk right past this window are the ones who earned the most. If you’ve spent thirty years as a high earner, nothing in your experience has trained you to treat a low-income year as an asset. So the cheapest tax years of your entire life slide by unused. And unlike almost every other planning move, these years do not come back.
I’ve written before about whether a Roth conversion is right for you. That post covers the mechanics in full, and I’d start there if conversions are new to you. This post is about something narrower and more urgent: the window itself. Why it’s use-it-or-lose-it, the three patterns that cause high earners to miss it, and how to tell whether you’re standing in it right now.
The Roth Conversion Window in Early Retirement
Quick refresher. While you’re working, your income is high, so moving money from a pre-tax 401(k) into a Roth is expensive: you’d be paying tax on the converted amount at your top rate. (If you’re still deciding where new contributions should go, that’s a different question, and I cover it in Roth vs. Traditional 401(k).)
Then you retire. The paycheck stops. But for a few years, before Social Security turns on (which for many of the women I work with is age 70) and before required minimum distributions begin, your taxable income drops to the lowest it will be for the rest of your life.
That low-income stretch is the conversion window. In those years, you can move pre-tax money into a Roth IRA, pay tax on it at bargain rates, and it never gets taxed again. Picture your income as a timeline: high bars while you’re working, a low trough in early retirement, then the bars jump back up when Social Security starts and required withdrawals begin. The trough is the window. A Roth conversion in early retirement is simply the act of using it while it’s open.
Why a Roth Conversion Before RMDs Is Use-It-or-Lose-It
Here’s the part that makes this urgent: you can’t get it back.
The window is not a strategy you can run whenever you feel ready. It’s a fixed amount of cheap-bracket room, available for a fixed number of years, and then it’s gone. Every year you’re in the window and don’t use it, that year’s low-bracket room vanishes. You can’t roll it forward to next year. There’s no catch-up provision.
And the window has a hard closing date. Required minimum distributions begin at RMD age: 73 if you were born between 1951 and 1959, 75 if you were born in 1960 or later. Once RMDs start, they force your income up permanently. Your brackets fill on their own with money you’re required to withdraw, and the cheap room is gone for good. That’s why a Roth conversion before RMDs is fundamentally different from one after: before, you choose what income to recognize and at what rate. After, the IRS chooses for you.
One more deadline inside the deadline: conversions have to happen within the calendar year, and since 2018 a conversion can’t be undone. A conversion you plan to do “soon,” in a window year that ends, is a conversion that never happened. This is one of the few financial decisions that is truly use-it-or-lose-it.
Three Ways High Earners Miss the Window
I see three patterns constantly, and none of them come from carelessness. They come from habits that served you well for thirty years.
One: you don’t recognize the dip. You’ve spent decades with a high income, so when it drops in early retirement, your brain reads it as “less money,” not “a tax opportunity.” You’ve never been trained to see a low-income year as valuable. It feels like a step down, so you don’t act on it. But that dip is the single most valuable retirement tax planning asset you will ever hold, precisely because it’s temporary.
Two: you wait to be sure. High earners are careful, analytical people. So you decide to wait and see how the first couple of retirement years go before doing anything irreversible. Reasonable instinct, wrong setting. Every year you spend waiting is a year of window room you can never recover. Caution, here, is expensive. It just sends you the bill twenty years later, when RMDs arrive on a larger balance.
Three: you let someone else close the window on you. The moment you turn on Social Security, your income jumps and the window narrows or disappears. And up to 85% of your benefit can itself be taxable, stacking on top of any conversion. A lot of women claim at 62 or 65 for peace of mind, without realizing they just shut their own conversion window years early. (Waiting also has its own payoff: delayed retirement credits grow your benefit roughly 8% for each year you wait past full retirement age, up to age 70.) And your CPA isn’t going to catch it either. They file what happened. They’re not the one sitting you down in June saying, “This is the cheapest tax year of your life. Let’s use it.” That gap between tax filing and tax planning is exactly where this window gets lost. It’s the same gap my free Executive Woman’s Tax Playbook is built to close. The years slide by, RMD age arrives, and the required withdrawals make the decision for you, the expensive way.
Missing the Window Compounds Into the Widow’s Penalty
Here’s the sting. Every dollar you don’t convert in the window stays in your pre-tax account and keeps growing. So your required withdrawals are bigger. Your brackets are higher. And the cost doesn’t stop with you.
If you’re married, when one of you passes, the survivor inherits that entire pre-tax balance and files as a single taxpayer. Same money, single-filer brackets, roughly half the bracket room. That’s the widow’s penalty, and I’ve done a full breakdown of how it works. A missed conversion window is one of the main ways it gets worse: the balance you didn’t convert at 22% gets forced out later at the survivor’s compressed single rates.
Missing the window doesn’t just cost you now. It quietly raises your taxes for the rest of two lifetimes.
Why Using the Window Feels Wrong (and Why That’s the Trap)
One more thing, because I see it with almost every client. Using the window means voluntarily paying tax you don’t technically have to pay yet. Your brain fights it. Writing a check to the IRS in a year when you finally have breathing room feels wrong.
But that’s exactly the trap. The comfort of not paying now is what costs you, and your survivor, so much more later. The women who do this well are the ones who can hold two things at once: yes, it’s uncomfortable to prepay tax, and yes, it’s one of the highest-impact moves available to me right now.
You don’t have to convert everything. You don’t even have to convert most of it. You just have to stop letting the window close on autopilot.
What to Do This Week
- Find out if you’re in the window. If you’ve stopped working (or will soon), haven’t started Social Security, and haven’t reached your RMD age (73 or 75, depending on your birth year), you are likely standing in it right now. That’s the trigger to act, not to wait.
- Map your projected income for every year until 70. For each year, estimate what will actually land on your tax return. Every year with room below the top of a sensible bracket is a year of window you can use or lose. Two numbers to watch while you map: conversion income raises the MAGI that sets your premium subsidy if you’re buying your own health insurance before Medicare, and because Medicare looks back two years, it can also trigger IRMAA surcharges on your future Part B premium.
- Check your Social Security claiming plan against your window. Before you file at 62 or 65 “for peace of mind,” run the numbers on what that claim does to your conversion room. Turning benefits on early can shut the window years ahead of schedule.
- Decide before December, not next spring. Conversions must happen within the calendar year, and since 2018 they can’t be undone, in either direction. A window year that ends unused is gone. Put a decision date on the calendar for this fall.
Want the full framework?
The tax moves behind this episode (the bracket planning, Roth sequencing, and account-location decisions I walk through with clients) are in my free guide, The Executive Woman’s Tax Playbook. It’s a free PDF you can read in one sitting. Get the playbook here.
Hazel Secco, CFP®, CDFA®, is the founder of Align Financial Solutions, a fee-only fiduciary firm that works with high-earning women and female executives on retirement planning, equity compensation, and tax strategy.
Already past the research phase? Book a free 15-minute Align Call: https://alignfinancialsolutions.com/book-a-call/
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Frequently Asked Questions
What is the Roth conversion window?
The Roth conversion window is the stretch of low-income years between retirement and required minimum distributions, often five to ten years, when you can move six figures from pre-tax accounts into a Roth at some of the lowest tax rates you will ever see. Once Social Security and RMDs push your income back up, that cheap-bracket room is gone for good.
Do RMDs start at age 73 or 75?
Required minimum distributions begin at 73 if you were born between 1951 and 1959, and at 75 if you were born in 1960 or later. Once they start, forced withdrawals raise your income permanently and close the conversion window. Before RMDs, you choose what income to recognize and at what rate; after, the IRS chooses for you.
Can a Roth conversion be undone?
No. Since 2018, a Roth conversion cannot be reversed, and every conversion must be completed within the calendar year. That is why I tell clients to put a decision date on the calendar for the fall instead of waiting until spring. A window year that ends unused is low-bracket room you can never get back.
Does claiming Social Security early hurt a Roth conversion strategy?
It can. Turning benefits on at 62 or 65 raises your income and can shut your conversion window years early, and up to 85 percent of your benefit can itself be taxable, stacking on top of any conversion. Delaying past full retirement age instead grows your benefit roughly 8 percent for each year you wait, up to age 70.
Disclaimer: Advisory services are offered through Align Financial Solutions LLC (“AFS”), an Investment Advisor in the State of New Jersey. This article is for educational purposes only and does not constitute personalized tax, legal, investment, or financial planning advice. Rules and figures are current for 2026 and subject to change. All client scenarios are hypothetical composites for illustration and do not represent any specific client outcome. Consult a qualified professional about your specific situation.
Sources
- Roth IRAs – Internal Revenue Service: https://www.irs.gov/retirement-plans/roth-iras
- Retirement Plan and IRA Required Minimum Distributions FAQs – Internal Revenue Service: https://www.irs.gov/retirement-plans/retirement-plan-and-ira-required-minimum-distributions-faqs
- Delayed Retirement Credits – Social Security Administration: https://www.ssa.gov/benefits/retirement/planner/delayret.html