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The Fed15 Podcast | Ep. 162: Working in Retirement + Roth Conversion Strategies

By STWS
08/04/2026

Dan and Katelyn discuss how federal employees can approach retirement income and tax planning, including the potential impact of working after retirement and the role Roth conversions may play in creating tax flexibility.


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The Fed15 Podcast | Ep. 162: Working in Retirement + Roth Conversion Strategies

Dan discusses what federal retirees should consider when continuing to work after leaving federal service. He covers how consulting, contract work, teaching, part time employment, and other earned income can interact with pensions, Social Security, TSP withdrawals, Medicare premiums, and investment income. Dan also explains the Social Security earnings test before full retirement age, potential tax considerations for consulting income, and common planning mistakes to watch for when multiple income sources overlap.

Katelyn discusses Roth conversions and how they can provide another source of tax flexibility in retirement. She explains how Roth conversions work, how federal employees may consider using lower tax brackets, and why paying conversion taxes from taxable funds may be worth evaluating. Katelyn also highlights potential benefits including tax diversification, managing future RMDs, estate planning considerations, and providing greater flexibility for surviving spouses.

 

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“Securities offered through Raymond James Financial Services, Inc., member FINRA/SIPC.  Investment advisory services offered through Raymond James Financial Services Advisors, Inc. Lee, Sipe & Associates, Inc. is not a registered broker/dealer and is independent of Raymond James.  Content represents the opinions of the speaker and not necessarily those of Raymond James.  Important Disclosure Information:  http://raymondjames.com/smicd.htm 

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PODCASTS

FEDLIFE Podcast

The FedLife Podcast is your in-depth, biweekly deep dive into the world of federal benefits and retirement planning. Hosted by federal benefits expert Ed Zurndorfer and Dan Sipe of Serving Those Who Serve, each 30-minute episode unpacks the complexities of FERS and CSRS retirement, FEHB and Medicare, survivor benefits, tax planning, and more. Designed for federal employees and retirees who want more than just the basics, FedLife goes beyond the headlines to explore the rules, nuances, and strategies that can make a meaningful difference in your retirement. Remember: it’s your Fed life, make it a great one.

 

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FED15 Podcast

The Fed15 Podcast is your weekly 15(ish)-minute briefing on federal benefits and financial planning, built specifically for federal employees and retirees. Hosted by Dan Sipe and Katelyn Murray of Serving Those Who Serve, each episode delivers clear, actionable guidance on topics like FERS and CSRS retirement, TSP strategies, FEHB, survivor benefits, tax planning, and more! Whether you’re five years from retirement or already there, The Fed15 helps you cut through the noise, avoid costly mistakes, and make confident decisions about your federal benefits.

 

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