Is Financial Software Giving You False Retirement Confidence? - 548
Your Money, Your Wealth
Your Money, Your Wealth
2.3 • 681 Ratings
🗓️ 23 September 2025
⏱️ 48 minutes
🧾️ Download transcript
Summary
Wendy and Joe in Colorado ran the numbers, and their financial planning software says they'll have over $10 million when they pass. Wendy's wondering if they should continue converting to Roth while working, despite their high tax bracket. But has the software lulled them into a false sense of security? That’s today on Your Money, Your Wealth® podcast number 548 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, which is smarter for "Kurt and Courtney" in New York: aggressively paying down their mortgage, or putting their extra money to work in the market before Kurt retires early in 20 years? Finally, when does it stop making sense for high-earners "Tim and Faith" in Boston to contribute to their Roth? The fellas duke it out on this one (and we figure out, based on our earliest musical interests, which era we’re each children of.)
Free Financial Resources in This Episode: https://bit.ly/ymyw-548 (full show notes & episode transcript)
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:11 - Financial Software Says We’ll Have $10M. Should We Continue Converting to Roth While Working, Despite Our High Tax Bracket? (Wendy, Loveland, CO)
16:35 - Watch 4 Hard Truths About Retirement You Need to Face on YMYW TV, Download the Retirement Readiness Guide
17:37 - What Are the Pros and Cons of Paying Off Our Home Before I Retire Early? (Kurt & Courtney, NY)
31:54 - Pay Off the Mortgage: YMYW Podcast Playlists on YouTube and Spotify, Calculate your free Financial Blueprint
32:51 - We're Late 40s With $3M + $2M RSUs. Continue Contributing to Tax-Deferred? Are We On Track for Retirement at 55 or 60? (Tim & Faith, MA)
46:15 - Next Week on the YMYW Podcast
46:37 - YMYW Podcast Outro
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Wendy and Joe in Colorado ran the numbers and their financial planning software says they'll have over $10 million when they pass. |
| 0:07.5 | Wendy's wondering if they should convert to Roth while working despite their high tax bracket. |
| 0:12.1 | But has the software lulled them into a false sense of security? |
| 0:15.7 | That's today on Your Money, Your Wealth podcast number 548. |
| 0:19.3 | Plus, which is smarter for Kurt and Courtney in New York, |
| 0:22.5 | aggressively paying down their mortgage or putting their extra money to work in the market |
| 0:26.4 | before Kurt retires early in 20 years. Finally, when does it stop making sense for high earners |
| 0:32.0 | Tim and Faith in Boston to contribute to their Roth? The fellas duke it out on this one, |
| 0:37.1 | and we figure out based on our earliest musical interests, which era were each children of. I'm executive producer Andy Last, and here are the hosts of Your Money, Your Wealth, Joy Anderson, CFP, and Big Al-Clopine CPA. Let's kick this thing up. First off, happy birthday, Andy Last. Oh, thank you. Thank you very much. 52. |
| 0:56.2 | Starting my 53rd year. |
| 0:57.8 | 53 is my lucky number. We'll see how that works out for me. |
| 1:00.7 | Oh, well, congratulations. |
| 1:02.7 | Thank you. Thank you very much. |
| 1:04.1 | Don't look a day older than 25. |
| 1:06.4 | Dang. Thank you, Joe. |
| 1:09.6 | All right. Speaking of 25, hi, Joe, big Al. This is Wendy from Lumberland, Joe. All right, speaking of 25, hi, Joe, Begall. |
| 1:12.6 | This is Wendy from Lumberland, Colorado, and my husband, Joe. |
| 1:16.6 | I'm 57. |
| 1:17.7 | My husband's 54. |
| 1:19.1 | My husband drives a 2019 Chevy Colorado. |
| 1:21.5 | I drive a 2025 GLE 450 E Mercedes hybrid. |
| 1:27.7 | Okay. Well, that sounds like a nice car. I think it Mercedes hybrid. Okay. |
... |
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