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)

Ultimate Guide to Roth IRAs - free download

Will Your Money Last Through Retirement? - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

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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

Joe Anderson, CFP® and Big Al Clopine, CPA tackle the fears that mess with even the best-laid financial plans, today on Your Money, Your Wealth® podcast 552. Big Wallet Barbie and Ken from the Midwest have saved millions, but Barbie's still worried about retiring early, buying a new house, and converting to Roth. Is she second-guessing her plans? The fellas spitball for Dan from Florida, who's flying high in the 35% tax bracket and trying to decide between Roth 401(k) contributions and future Roth conversions. They also float a surprising idea - one that's rare on YMYW - for a listener from Chicago who is FIRE'd Up about Roth vs. pre-tax and making a tax-smart wealth transfer. We'll wrap up with a couple of your comments.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-552 (full show notes & episode transcript)

Emotionless Investing Guide

The Truth About Your Love/Hate Relationship With Money - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Connect With Us:

YouTube: Subscribe and join the conversation in the comments

Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

Chapters:

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

00:49 - Big Wallet Barbie and Ken's Roth Conversion, Retirement, and Home Purchase Strategy (Barbie Mattel, Midwest)

08:58 - Roth 401(k) Contributions or Roth Conversions? Flying High in the 35% Tax Bracket (Dan, FL)

17:23 - High-Earners Planning FIRE and Wealth Transfer: Roth, Pre-Tax… Life Insurance? (FIRE'd Up, Chicago)

29:56 - Correction on Spousal Social Security Benefits After the Fairness Act (Cindy)

33:37 - Follow Up: The Kids Are Pretty Alright (Lucas, MN)

34:44 - Outro: Next Week on the YMYW Podcast

We're playing "which comes first" today on Your Money, Your Wealth® podcast number 551 with Joe Anderson, CFP® and Big Al Clopine, CPA. "Retired G-Man and Nurse Ratched" from Pennsylvania have saved $2 million. Should they withdraw money first from their IRA or their taxable accounts in retirement? "Mike and Carol in Florida" want to know when and how much to convert to Roth, but they're also sitting on a mountain of company stock. Should they deal with that first? Mackey in Florida is 55 and wonders if he can retire now with $2.6 million and some lingering debt - but there's an important first he's missing too! Plus, Mike in Utah asks Joe and Big Al to spitball on a plan for his 90-year-old mom's $1.9 million annuity, and Doc McMuffin in Minnesota asks for the fellas' take on her plan to gift appreciated assets to her parents.

Free Financial Resources in This Episode:

https://bit.ly/ymyw-551 (full show notes & episode transcript)

YourMoneyYourWealth.com - all our financial resources! Ask Joe and Big Al, blogs, workshops, financial guides, and 11 seasons of YMYW TV!

10 Big Retirement Regrets to Avoid (Before It's Too Late) - YMYW TV

Financial Blueprint (self-guided)

Financial Assessment (Meet with an experienced professional)

REQUEST your Retirement Spitball Analysis

DOWNLOAD more free guides

READ financial blogs

WATCH educational videos

SUBSCRIBE to the YMYW Newsletter

Connect With Us:

YouTube: Subscribe and join the conversation in the comments

Podcast apps: subscribe or follow YMYW in your favorite

Apple Podcasts: leave your honest reviews and ratings

Chapters:

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

00:53 - How to Retire at 55 With $2.6M and Debt? First, How to Write a Good Spitball Request (Mackey, FL)

03:46 - Sequence of Retirement Withdrawals: IRA First or Taxable First? (G-Man and Nurse Ratched, PA)

12:10 - Roth Conversions vs Concentrated Stock: Which Comes First? (Mike & Carol, FL)

29:27 - What to Do With 90-Year-Old Mom's $1.9M Annuity? (Mike, UT)

40:59 - Is Gifting Appreciated Assets to Parents Tax-Smart or Risky? (Doc McMuffin, MN)

48:27 - Outro: Next Week on the YMYW Podcast