Should You Convert to Roth Before or After You Retire? - 553

Your Money, Your Wealth

Realestate, Income, Investing, Personalfinance, 401k, Rothconversion, Retirement, Education, Taxes, Socialsecurity, Personalfinances, Finance, Retirementplanning, Investments, Stocks, Business, Roth, Fiduciary, Ira

2.3 • 681 Ratings

🗓️ 28 October 2025

⏱️ 41 minutes

🔗️ Recording | iTunes | RSS

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Summary

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.

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

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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

Transcript

Click on a timestamp to play from that location

0:00.0	Joe and Big Al tackle one of the trickiest time and questions in retirement planning.
0:04.3	Today on Your Money, Your Wealth podcast number 553.
0:07.8	When should you convert to Roth while you're still earning or after retirement?
0:11.7	But first, James from Texas wonders if it's worth maxing out his high fee 457 plan or if he's
0:17.4	better off investing in a low-cost brokerage account.
0:20.0	Full-time travelers, Lois and Clark want to know how much they should keep converting to Roth
0:24.4	now that they're on Medicare.
0:26.2	Ray Charles in Chicago is burnt out on corporate life and plans to quit at 55.
0:31.2	Is that the perfect time for him to start Roth conversions?
0:34.2	And finally, Gun and Rose from Louisiana asked if borrowing again from their 401k is a
0:40.1	smart move. Our email inbox is so full, it's making the servers grown with all of your questions,
0:45.9	but the fellas are doing the best to cruise through them. I'm executive producer Andy Last,
0:50.5	and here are the hosts of Your Money, Your Wealth, Joe Anderson, CFP, and Big Al-Clopine CPA.
0:56.9	All right, let's go to Texas. We got James. He writes in. He's like, hey, y'all. Love the show.
1:03.5	I work for a local government and have access to a 457B account. I'm currently contributing 6% of my pay.
1:09.6	I make about $135,000 a year, but I'm considering
1:12.5	maxing out this account now. My hold-up is that the funds I have to choose from have pretty high
1:19.4	expense ratios. Is it worth getting the tax benefit to max this account, or should I invest to spare
1:26.2	money in a taxable brokerage with low cost and
1:29.5	potentially zero expense ratios. My wife and I live in Texas with two beautiful girls.
1:35.8	We don't drink much, but when we go on a cruise, I would say nothing is off limits. Wow. Wow. Look at
1:43.3	James. You've been on a cruise lately? I have never been on a cruise. Never? No. Oh, okay. He just lives with nothing off limits. I would love to go on a cruise with James. Yeah, where nothing's off limits. Hey, y'all, let's go to the bar. Let's do it.
	...

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