AI Summary
5 min readThe Housing Overlap Headache and How to Solve It
Wes Moss, a retirement researcher and author of the forthcoming The Retire Sooner Method, joined Krista DeBias on the Clark Howard podcast to tackle two practical problems that trip up retirees: where to live and how to pay for the new place before the old one sells. The conversation also wove in listener questions about fees, annuities, and early retirement math, but the core of the episode was a real-world case study that illustrates a systematic approach to a common financial squeeze.
A Systematic Way to Find Your Retirement Community
Moss began with a framework for choosing where to live in retirement, anchored in his research on what makes retirees happy. One of his earliest findings: happiness rises the more adult children you live near. "If you've got four kids and they're all in different states spread out around the country, it just makes seeing everybody a lot harder," he said. Proximity to family matters more than topography or climate.
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What you'll learn
- 1 (01:05) **Welcome & Setting the Stage** - Krista DeBias introduces Wes Moss, who frames the episode around a two-part retirement housing dilemma.
- 2 (04:42) **Part 1: Systematically Finding Your Retirement Community** - Wes Moss outlines a three-step process for choosing a retirement location, using a real client ("Joe") as an example.
- 3 (07:07) **Joe's Criteria for a Retirement Community** - A detailed look at the five specific criteria Joe used to find his next home, which serves as a template for listeners.
- 4 (09:42) **Part 2: The Housing Overlap Headache & Funding Underlap** - Wes Moss introduces the core financial problem: how to buy a new home without selling your current one, without taking a mortgage, and without triggering a massive tax bill.
- 5 (09:52) **Listener Question: SoFi High-Yield Savings Account** - Kathleen from Ohio asks about the safety of parking $50k in a SoFi high-yield savings account.
- 6 (11:40) **Listener Question: TSP vs. Roth IRA Rollover** - Makita, a retired Marine, asks if they should transfer their Roth TSP to a Fidelity Roth IRA.
- 7 (14:26) **Listener Question: Edward Jones Fee Analysis** - Doug from Oklahoma asks if his total fee of ~0.64% at Edward Jones is reasonable, given he gets personal service.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
How To Find (and Afford) Your Dream Home in Retirement
Deciding where to spend your retirement is one of the most significant transitions you’ll ever make, but it requires a systematic approach to get it right. Whether you plan to stay in your current home or relocate to a new destination, your environment directly impacts your long-term happiness. In this episode, Wes Moss shares tips to find – and afford – your dream community in retirement. Many retirees face the "housing overlap headache," where you find your new home in five minutes, but it takes five months to sell your old one. If you don't want to carry a mortgage or trigger a "tax tsunami," Wes breaks down a strategy that can help.
Plus, Christa shares your #AskWes questions and Wes gives his take. All this and more on the April 14, 2026, Ask an Advisor episode of the Clark Howard podcast. Submit your questions at clark.com/ask.
We hope you enjoy our weekly Ask An Advisor episodes. Let us know what you think in the comments!
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