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Is There an Ideal Time for a Roth Conversion? A Pre-Retiree’s Guide

November 26, 2025

Article Overview

  1. What is a Roth Conversion?
  2. A Hidden Opportunity
  3. A Roth Conversion Example Scenario
  4. Why Women May Benefit
  5. Is a Roth Conversion Right for You?
For many women approaching retirement, there’s a quiet shift that happens behind the scenes, not just in your schedule or your sense of identity, but in your tax picture.  As work income tapers off and Social Security hasn’t yet begun, your taxable income often dips into a lower bracket. This transition period can open a unique window of opportunity for something called a Roth conversion. At Pleasant Wealth, we often talk with women who want financial clarity, not complexity. Roth conversions sound technical or intimidating, but the underlying idea is simple: it’s a strategy to proactively manage taxes so your future self — especially your older, retired self — has greater flexibility and fewer surprises. Let’s walk through what a Roth conversion is, why timing matters, and how one pre-retiree found her “just right” moment.

What Is a Roth Conversion, Really?

A Roth conversion is the process of moving money from a traditional IRA or pre-tax retirement account into a Roth IRA. Here’s what changes:
  • Traditional IRA: You contributed pre-tax money, meaning you didn’t pay taxes at the time you contributed. So you owe taxes when you take withdrawals later.
  • Roth IRA: You contribute after-tax dollars, and you’ve already paid taxes on them. Qualified withdrawals in retirement are tax-free.
When you convert from a traditional IRA to a Roth, you pay taxes in the year of the conversion — but in exchange, you get the long-term benefit of tax-free withdrawals and no required minimum distributions later in life. This isn’t right for everyone. But for many women in the “bridge years” between full-time work and taking Social Security, it’s worth exploring.

The Transition to Retirement: A Hidden Opportunity

The years just before and after retirement can create a natural dip in income. For example, when someone leaves full-time work at 62 but delays Social Security until 67, their taxable income may be significantly lower during those five years. This creates a window where converting some of their traditional IRA balance may result in lower taxes than if they wait until later retirement, when Social Security income, portfolio withdrawals, and eventually required minimum distributions stack up. Think of this period as a tax planning sweet spot, a time when intentional action can create meaningful future benefits, especially for women who want to reduce financial stress in later life.

Meet Elaine: A Pre-Retiree Finding Her Window

Elaine, age 63, recently stepped away from a demanding career to give herself space to breathe, travel, and reconnect with what’s important to her. Like many women we work with, she wasn’t worried about “beating the market.” What she wanted was a plan that felt thoughtful, calm, and aligned with her picture of a secure retirement. She had saved diligently in her employer’s retirement plan over the years, building a healthy 401(k) balance. But she hadn’t thought much about future taxes or how her tax bracket might change once regular paychecks stopped. During her first year of semi-retirement, Elaine noticed something surprising: her taxable income was far lower than in any year she could remember. She wasn’t taking Social Security yet. She wasn’t tapping heavily into her portfolio. Her income dip was unplanned, but it turned out to be an opportunity. Elaine’s financial advisor ran a tax-awareness projection to see how her income might look in later years. What stood out was the period between now and age 70 — before Social Security, before increased portfolio withdrawals, and before required distributions started. That window became the center of her Roth conversion strategy. The plan wasn’t dramatic or risky. It simply called for gradually converting a portion of her traditional IRA each year during these lower-income years. There were no extreme bets, no push into high tax brackets, and no pressure to make the “perfect” decision. Instead, it was about giving Elaine more control:
  • Over how much tax she paid and when
  • Over-reducing the impact of future required distributions
  • Over-simplifying her income picture later in life
  • Over creating a pool of tax-free money she could use however she wanted — gifting, travel, or healthcare expenses
Most importantly, the plan felt peaceful to her. It matched her desire for financial stability and flexibility rather than complication.

Why Women in Particular May Benefit

A Roth conversion strategy can be especially powerful for women approaching retirement because:
  • Longevity means a longer retirement to plan for. Tax-free withdrawals later can help stretch resources.
  • Required minimum distributions can increase taxable income significantly. Converting earlier may help reduce their future impact.
  • Women often value financial independence and flexibility. Roth accounts offer both — no mandatory withdrawals and tax-free access in later years.
  • A lower-income gap year can be more common. Women who step back from full-time work sooner or phase into retirement often create natural windows for strategic planning.
Not everyone needs or benefits from a Roth conversion. But it’s worth asking the question — especially if you’re approaching retirement or already in your first few lower-income years. A few signs that a conversation may be helpful:
  • You expect your tax rate to increase later in retirement.
  • You’re delaying Social Security.
  • You have a significant balance in a traditional IRA or 401(k) account.
  • You want more flexibility in how you draw income later on.
  • You’re motivated by creating a smoother, more predictable financial future.

A Gentle Next Step

If you’re curious whether you’re in your own “conversion window,” our team at Pleasant Wealth is here to help you explore it without pressure or jargon. And as part of the process of becoming a client, you’ll go through our Permission to Retire onboarding, which can be helpful in understanding the pieces of retirement like Roth conversions.  Reach out to us anytime, or directly schedule a meeting to get to know each other better. We’d be glad to walk through your options and help you make a thoughtful, values-aligned decision. – Disclaimer: The examples included in this article are fictional and are meant for educational purposes only. It is not meant as specific tax or financial advice. You should consult a tax, legal, or financial professional before making any decisions.
Liz Hand, certified financial planner, sitting in the Pleasant Wealth office in Canton Ohio

About the Author

Clinton Miller, CFP®, is an investment advisor & financial planner with an educational background in mathematics.  He enjoys making tax planning relevant for clients so they can make confident money decisions. 

He and his wife Aubrey are based in Canton, OH & have two sons.  In his spare time, he enjoys fishing, chainsaw repair, & mucking around in the woods.

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