High Net Worth Pre-Retirees Share Their Biggest Fear (Here's How to Calm It) - 566
Your Money, Your Wealth
Your Money, Your Wealth
4.6 • 790 Ratings
🗓️ 27 January 2026
⏱️ 53 minutes
🧾️ Download transcript
Summary
"Mr and Mrs Smith" have nearly $850,000 saved at age 43, but they're very concerned about retirement. "Lucy and Desi" are 58 and 64 with nearly $7 million saved, but they still lie awake wondering if it's enough for their high-expense life. "Tony and Carmela" are in a similar boat with millions saved at 61 and 59, but they're worried their asset allocation won't get them through their retirement. No matter the numbers, the fears sound exactly the same: will you run out of money in retirement? Turns out overcoming that fear is not about hitting a magic number. We'll find out what it's all about today on Your Money, Your Wealth podcast number 566 with Joe Anderson, CFP®, and Big Al Clopine, CPA. The fellas also spitball Roth conversions, long/short direct indexing capital gains tax strategies for "Juicy Squeeze", working after retirement for Wendi, and how one confusing word can completely change a retirement timing decision for "Jacques and Johana."
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https://bit.ly/ymyw-566 (full show notes & episode transcript)
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:01 - 43 With $850K. Am I Too Late to Build Enough Roth Money? (Mr & Mrs Smith, Dallas, TX)
11:29 - Nearly $7M Saved at 58 and 64. Do We Have Enough for a High-Spend Retirement? (Lucy & Desi, Jersey Shore, NJ)
23:38 - 61 and 59 With $4.5M Saved. Can I Retire Now With a 50/50 Portfolio? (Tony & Carmela, San Ramon, CA)
32:09 - Mid-50s with $685K Saved. Can One Spouse Retire While the Other Works? (Jacques & Johana, Florida)
38:53 - Are Long-Short Direct Indexing Tax Strategies Worth the Fees? (Juicy Squeeze)
47:04 - Should I Work as an Employee or Contractor After 70 on Social Security? (Wendi)
52:04 - Outro: Next Week on the YMYW Podcast
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Mr. and Mrs. Smith have nearly $850,000 saved at age 43, but they're very concerned about |
| 0:06.2 | retirement. Lucy and Desi are 58 and 64 with nearly $7 million saved, but they still lie awake |
| 0:12.5 | wondering if it's enough for their high expense life. Tony and Carmela are in a similar vote |
| 0:17.0 | with millions saved at 61 and 59, but they're worried their asset allocation won't get |
| 0:21.7 | them through their retirement. No matter the numbers, the fears sound exactly the same. Will we run |
| 0:27.7 | out of money in retirement? Turns out, overcoming that fear is not about hitting a magic number. |
| 0:32.8 | We'll find out what it's all about today on Your Money, Your Wealth podcast number 56. |
| 0:43.3 | Joe and Bigel also spitball rock conversions, long short, direct indexing capital gains tax strategies for juicy squeeze, working after retirement for Wendy, and how one confusing word |
| 0:48.7 | can completely change a retirement timing decision for Jacques and Johanna. |
| 0:52.9 | I'm executive producer Andy Last and here are the |
| 0:55.3 | hosts of your money, your wealth, Joe Anderson, CFP, and Big Al Clopine CPA. |
| 1:01.3 | Mr. and Mrs. Smith. Joe, I love the podcast. Been listening for about a year. And it's one of |
| 1:08.8 | my regular rotations to listen to when I'm taking my morning three |
| 1:12.5 | mile walk. Three mile walk. How long does that take? An hour? Yeah, I think when I'm walking, |
| 1:19.2 | it's about a, yeah, three miles, 20 minutes, yeah, that's been an hour. Is it? Mm-hmm. |
| 1:24.7 | I drive a 2019 Chevy Traverse. |
| 1:30.2 | That's the company car. |
| 1:32.5 | My wife drives a 2020 Ford Fusion that will be giving to my daughter next year. |
| 1:38.9 | Drink of choice, a local craft beer. |
| 1:41.4 | I've never tried it before. |
| 1:43.3 | Oh, a local craft beer I've never tried before. |
| 1:45.8 | He likes new ones. Oh, yeah. Preferable, a IPA, hazy or West Coast? Okay, I'll go, I'll go with the |
... |
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