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October 28, 2025 40 mins

Joe Anderson, CFP® and Big Al Clopine, CPA tackle one of the trickiest timing questions in retirement planning, today on Your Money, Your Wealth podcast number 553: when should you convert to Roth, while you're still earning, or after retirement? First, James from Texas wonders if it's worth maxing out his high-fee 457 plan, or if he's better off investing in a low-cost brokerage account. Full-time travelers "Lois and Clark" want to know how much they should keep converting to Roth now that they're on Medicare. Ray Charles in Chicago is burned out on corporate life and plans to quit at 55. Is that the perfect time for him to start Roth conversions? And finally, Gun and Rose from Louisiana ask if borrowing again from their 401(k) is a smart move.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-553 (full show notes & episode transcript)

Retirement Lifestyles Guide - free download

Ultimate Guide to Roth IRAs - free download

Will Your Money Last Through Retirement? - YMYW TV

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Chapters:

00:00 - Intro: This Week on the YMYW Podcast

00:56 - 457(b) vs. Brokerage: Are High Fees Worth the Tax Break? (James, TX)

06:43 - Roth Conversions in Retirement: Hitting the Road and the 12% Bracket ("Lois & Clark", FL)

19:54 - Early Retirement Pivot: Quit at 55 and Convert to Roth? ("Ray Charles", Chicago, IL)

33:28 - Should We Borrow From 401(k) For Home Repairs? (Gun & Rose, LA)

38:54 - Outro: Next Week on the YMYW Podcast

 

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