Retirement Changes at These 5 Major Financial Crossroads - 569
Your Money, Your Wealth
Your Money, Your Wealth
4.6 • 790 Ratings
🗓️ 17 February 2026
⏱️ 44 minutes
🧾️ Download transcript
Summary
When you're standing at a major financial crossroads, the timing of your decisions can mean the difference between success and failure. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on the "when" of five retirement decisions, today on Your Money, Your Wealth podcast number 569. We'll kick things off with a whale of an email: "Fine and Dandy" is 42 years old with a multimillion dollar private equity offer on the table. Should he sell his business now or hold out for a second bite of the apple later? He also wonders if it's crazy to spend more on his vacation home than on his primary residence. David calls himself an "elderly orphan," flying solo at 66 and in need of a plan to protect his million-dollar portfolio as he ages. BB and Shell are trying to time their final year of retirement contributions to save as much as possible before moving to a lower-tax state. Should they go Roth IRA or traditional? Joel wonders when to take required minimum distributions from retirement accounts for the maximum tax benefit, and Brian in New York needs a spitball on when it makes sense to have an emergency fund as a retiree, and for how much.
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https://bit.ly/ymyw-569 (full show notes & episode transcript)
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Chapters:
00:00 - Intro: This Week on the YMYW Podcast
01:09 - Should I Sell My Business or Wait? Is It Crazy to Spend More on My Vacation Home Than My Primary Residence? (Fine and Dandy, IL)
20:48 - Saving to Roth IRA vs Traditional IRA in the Final Year Before Retirement (BB and Shell)
23:50 - When to Take Your First RMD for the Maximum Tax Benefit (Joel, CA)
27:33 - Aging Alone in Retirement: How to Protect Assets Before Cognitive Decline (David, 68, Logan, NM)
35:37 - Why Some CPAs Cap Roth Conversions at $500K AGI (Shweta, CA)
37:05 - When Does It Make Sense for Retirees to Have an Emergency Fund - and How Much? (Brian, Albany, NY)
42:03 - Outro - Next Week on the YMYW Podcast
Transcript
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| 0:00.0 | When you're standing at a major financial crossroads, the timing of your decisions can mean the difference between success and failure. Join Big Al Spitball on the when of five retirement decisions today on Your Money, Your Wealth podcast number 569. We'll kick things off with a wail of an email. Find it Dandy is 42 years old with a multi-million dollar private equity offer on the table. |
| 0:22.3 | Should he sell his business now or hold out for a second bite of the apple later? |
| 0:26.7 | He also wonders if it's crazy to spend more on his vacation home than his primary residence. |
| 0:31.1 | David calls himself an elderly orphan, flying solo at 66 and in need of a plan to protect his million dollar portfolio as he ages. |
| 0:39.5 | Bibi and Shell are trying to time their final year of retirement contributions to save as much |
| 0:43.9 | as possible before moving to a lower tax state. Should they go rough IRA or traditional? |
| 0:49.5 | Joel wonders when to take required minimum distributions from retirement accounts for the maximum tax benefit. |
| 0:55.5 | And Brian in New York needs a spitball on when it makes sense to have an emergency fund as a retiree and for how much. |
| 1:01.9 | I'm executive producer Andy Last and here are the hosts of your money, your wealth, Joe Anderson, CFP, and Big Al Clopine CPA. |
| 1:09.8 | Fine and Dandy from Illinois. |
| 1:12.3 | Good afternoon, Big Al, Joe, and Andy, first time writing. |
| 1:16.8 | First time writing. |
| 1:18.7 | And so I hope I'm doing this right, and I'm not using any big words to trip you up. |
| 1:24.2 | Too late. |
| 1:26.2 | Just write normal. |
| 1:30.1 | I love your take on a spitball. |
| 1:31.9 | I've been listening to your show for a little over a year. |
| 1:34.3 | I binge episodes while in the sauna. |
| 1:36.9 | You have to work out at the gym. |
| 1:39.3 | Awesome. |
| 1:42.0 | Is that fine or dandy? |
| 1:49.2 | Just hanging out in the sauna, the towell on neither good boy i always catch the new weekly episodes and work on my way backwards whenever it's not tuesday afternoon |
... |
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