Your Money, Your Wealth: Don’t Let Money Anxiety Ruin Your Retirement (Episode 552)

Hosts: Joe Anderson, CFP® & Alan “Big Al” Clopine, CPA
Date: October 21, 2025

Episode Overview

In this episode, Joe and Big Al dig into the surprising persistence of financial anxiety—even among savers who appear well set for retirement. Through their signature blend of humor and expert advice, they analyze real listener scenarios with millions in savings questioning their readiness to retire, contribution and conversion strategies for high-income earners, and how best to transfer wealth to future generations. The episode focuses on cutting through emotional hang-ups about spending, optimizing tax strategies, and handling legacy planning—all while keeping things approachable and fun.

Key Discussion Points & Insights

1. Barbie & Ken in the Midwest: Can They Retire Early?

[00:49–07:14]

Situation:

• Barbie (56) and Ken (70) have over $3.3M saved; Ken receives a $127K pension (with COLA) and $61K Social Security; Barbie will get her own pensions and Social Security later.
• They want to spend $18K–$22K—possibly per month (though initially stated as annual)—after tax in retirement.
• No mortgage, comprehensive investment accounts, and substantial fixed income.

Highlights:

• Immediate Reaction:

  • Joe Anderson [02:46]: “Waving right in, you’re fine.”
  • Both hosts conclude Barbie can retire comfortably, regardless of whether the spending number is monthly or yearly.

• Discussion on Financial Anxiety:

  • Andi Last [04:48]: “Is this another one of those situations where we’ve got a couple with a big wallet who is having financial anxiety even though they are fine for it because they’re not used to the idea of spending without earning?”
  • Big Al Clopine [05:05]: “That’s not all that uncommon, really…once they turn off the paycheck, they freak out, even though they got plenty.”

• Soft Side of Retirement:

  • Joe Anderson [05:52]: “A lot of people that have done really good savings have a hard time spending… there’s anxiety around it, there’s guilt around it… But there’s a lot more, I guess, the softer side of money.”

• Roth Conversion Strategy:

  • Hosts suggest converting at least up to the 22% or 24% tax bracket, especially considering future “widow’s tax” issues due to age difference.

Quote:

• Joe Anderson [04:30]: “Thank you for spitballing my Barbie dream. I guarantee Barbie spends more than $20,000 on the Barbie Corvette, the Barbie beach house...”

2. Dan in West Palm Beach: Roth 401(k) Contributions vs. Future Conversions for High Earners

[08:58–17:16]

Situation:

• Dan (58) earns ~$680K/year, in the 35% tax bracket, and puts over $200K/year away. Nearly $1.3M already in Roths.
• Interested in whether to continue Roth 401(k) contributions or focus on pre-tax now and convert later.

Highlights:

• Analysis of Current and Future Tax Rate:

  • Big Al Clopine [14:19]: “Inflating assets with savings… I get a 2.6% distribution rate. Looking great.”
  • Joe Anderson [15:17]: “He’s going to be in a lower tax bracket when he retires… Because he doesn’t have that giant 401(k), it’s all in Roth.”

• Roth vs. Pre-tax Psychology:

  • Joe Anderson [15:33]: “I would not do conversions today, no. I would do the contributions to the Roth… this is all psych, you know, the site play.”
  • Big Al Clopine [16:05]: “It’s a pretty low fixed income. Anyway, I think I certainly agree with you on the Roth conversions. I would not do that till he retires.”

• Decision Framework:

  • Continue Roth 401(k) contributions given his already high pre-tax savings and future lower tax rates post-retirement.
  • Defer Roth conversions until after retirement when income is lower.
  • Use SEP Roth for side income if possible.

Quote:

• Big Al Clopine [17:04]: “As an accountant, it pains me to not do regular 401(k) contributions when you’re in the 35% bracket. So, you could argue what I just said.”

3. "Fired Up" in Chicago: Roth vs. Pre-tax for High-Income Earners With Legacy Planning Focus

[17:16–29:04]

Situation:

• Early 50s, $3.3M in 401(k), $500K in Roth, $2.5M in brokerage; currently earning $800K but expects to reduce income to $300K in 5 years.
• Wants advice on maximizing estate transfer to high-income children, especially minimizing inherited pre-tax IRA taxes.

Highlights:

• Switching to Roth Contributions:

  • Joe Anderson [21:26]: “I would definitely switch to Roth for sure.”
  • Emphasizes ease of mega backdoor Roth contributions via 401(k), especially in light of already large pre-tax balances.

• Forecasting Future RMDs & Tax Rates:

  • Joe Anderson [23:30]: “That thing could be at $10M at least... He’s gonna be in the 35 or 37% tax bracket at RMD age.”
  • The risk of growing pre-tax accounts into much higher RMDs and correspondingly higher taxes—possibly at higher rates than current.

• Psychological Benefits of Roth Saving:

  • Joe Anderson [25:19]: “If he goes after-tax, it’s the same as a conversion, but he just doesn’t have to write the check. It’s easier.”

• Estate-Planning Twist:

  • Joe Anderson [26:12]: “If he really wants to leverage wealth for the kids, why wouldn’t he buy a life insurance contract?”
  • Life insurance suggested for efficient wealth transfer (using irrevocable trust) rather than relying solely on retirement accounts.

• Conversion Timing:

  • Big Al Clopine [27:29]: “When you go down to $300,000, you can convert in the 24% bracket... then when you retire fully, I’d do even bigger conversions.”

Quotes:

• Joe Anderson [24:18]: “You’re going to forget that savings money the next day and you’re going to be happy you have this big chunk of change sitting in your Roth.”
• Big Al Clopine [28:16]: “That’s how I would think about it. Yes, it will benefit your kids, but I don’t know… that’s in the back of your mind.”

4. Listener Comments: Social Security Clarification & Family Updates

[29:56–34:44]

Notable Listener Moment:

• Cindy’s Social Security Tip:
  • Cindy writes in to correct/clarify a previous Social Security spousal benefit explanation, recommending listeners always proactively apply for spousal benefits as SSA likely will not do so automatically.
  • Joe Anderson [32:22]: "Absolutely… sometimes there’s errors, sometimes you assume… contact Social Security Administration to make sure you’re getting all the benefits that you’re entitled to.”

Lighthearted Feedback:

• Lucas from Minnesota checks in to confirm he does love his “pretty all right kids” after ribbing from Joe and Al.
• Big Al [34:30]: “There you go, Andy.” (for producer Andi Last getting a well-earned shoutout.)

Timestamps for Important Segments

• [00:49–07:14] Barbie & Ken’s Retirement Fears and Plan
• [08:58–17:16] Dan's High-Income Roth Decision Analysis
• [17:16–29:04] Tax-Smart Legacy Planning and Mega Backdoor Roth Tactics
• [29:56–34:44] Listener Corrections and Family Updates

Notable Quotes & Memorable Moments

“A lot of people that have done really good savings have a hard time spending. And I get it, there’s anxiety around it, there’s guilt around it…. There’s a lot more, I guess, the softer side of money.”
— Joe Anderson [05:52]

“If you can see you’ve got millions when you pass away… and if you want to start giving while you’re living, which feels better, and you get a tax break, that can be a great way to do it.”
— Big Al Clopine [06:25]

“This is all psych, you know, the site play. Because I’m not going to miss the taxes in 10 years. When I go on my cruises, I’d much rather not pay a bunch of tax then.”
— Joe Anderson [15:48]

“If he really wants to leverage wealth for the kids, why wouldn’t he buy a life insurance contract? Set up an irrevocable trust and have the kids buy several million dollars on both you and the spouse’s life.”
— Joe Anderson [26:12]

Episode Tone and Takeaways

The hosts maintain their trademark playful and irreverent tone while tackling serious financial concerns. They emphasize that money anxiety can persist regardless of account size, but most fears can be relieved by running the numbers and understanding both the mathematical and psychological components of retirement planning. They repeatedly encourage listeners to consider not just tax rates but also personal comfort with spending, strategies for legacy planning (including insurance and Roth optimization), and always double-checking on government benefits.

For More Resources

• Download the Emotionless Investing Guide (link from episode description)
• Watch related episodes and access free planning tools at YourMoneyYourWealth.com

Summary prepared for listeners who want to skip straight to the wisdom (with none of the financial anxiety).