Roth Conversions Before And After Retirement: What’s Different?

Thayer Partners Thayer Partners December 08, 2025

Discover the critical differences and key opportunities for maximizing your retirement savings through Roth conversions before and after you retire.

Understanding Roth Conversions: The Essentials

A Roth conversion involves moving funds from a traditional retirement account, such as a Traditional IRA or 401(k), into a Roth IRA. This process allows your assets to grow tax-free and provides the potential for tax-free withdrawals in retirement. However, converting comes with an immediate tax bill on the converted amount, making timing and strategy critical.

Understanding the fundamentals of Roth conversions is vital for business owners and executives looking to optimize their retirement plans. The decision to convert should be informed by your current income, tax bracket, and long-term financial objectives. As tax laws and income levels change over your career and into retirement, so do the considerations surrounding a Roth conversion.

Key Benefits of Converting Before Retirement

Converting to a Roth IRA while still working offers several advantages. For many executives and business owners, income is at its peak pre-retirement, but so are opportunities to manage taxable income through deductions, deferred compensation, or business expenses. By strategically converting portions of your traditional accounts during lower-income years or after retirement but before Required Minimum Distributions (RMDs) begin, you can minimize the tax impact.

Additionally, completing conversions before retirement allows your investments more time to grow tax-free, potentially amplifying the benefits as compound growth accumulates over the years. Pre-retirement conversions also offer flexibility in managing future tax liabilities, especially if you anticipate higher tax rates down the road.

Why Post-Retirement Roth Conversions Require a Different Approach

After retirement, your income profile changes significantly—often dropping, but sometimes increasing if you begin taking Social Security, pensions, or RMDs. This shift opens up new windows for Roth conversions, particularly in the years between retirement and age 73 (when RMDs from traditional IRAs begin).

Post-retirement conversions require careful coordination with other income sources to avoid bumping into higher tax brackets or increasing Medicare premiums due to IRMAA (Income Related Monthly Adjustment Amount). Business owners and executives should analyze their post-retirement cash flow and tax situation annually to determine optimal conversion amounts and timing.

Tax Implications to Consider at Every Stage

Taxes are the central consideration in any Roth conversion strategy. Converting while working might mean paying taxes at your highest marginal rate, but could be offset by deductions or business losses. After retirement, lower ordinary income may present an opportunity to convert at a lower rate, but this window can be short-lived if RMDs or other income sources begin.

Additionally, large conversions can trigger unintended consequences, such as pushing income into higher tax brackets, affecting eligibility for tax credits, or increasing Medicare premiums. It's crucial to model out the tax impact over several years, not just in the year of conversion.

Strategic Planning Tips for Maximizing Roth Conversion Success

For business owners and executives, a multi-year, forward-looking plan is essential for maximizing the benefits of Roth conversions. Consider converting smaller amounts over several years to avoid large tax spikes and maintain control over your tax bracket. Align conversions with years of lower income, such as early retirement or gap years before Social Security and RMDs begin.

Work closely with tax and financial advisors who understand the complexities of high-net-worth financial planning. Employ tax modeling software or advanced forecasting tools to simulate various scenarios and select the most advantageous conversion schedule. Proactive, personalized planning is the key to unlocking the full power of Roth conversions for your retirement strategy.

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This material prepared by Thayer Partners is for informational purposes only.  It is not intended to serve as a substitute for personalized investment advice or as a recommendation or solicitation of any particular security, strategy or investment product.  Thayer Partners is a Registered Investment Adviser. SEC Registration does not constitute an endorsement of Thayer Partners by the SEC nor does it indicate that Thayer Partners has attained a particular level of skill or ability. The material has been gathered from sources believed to be reliable, however Thayer Partners cannot guarantee the accuracy or completeness of such information, and certain information presented here may have been condensed or summarized from its original source.  Thayer Partners does not provide tax or legal or accounting advice, and nothing contained in these materials should be taken as such.

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