08.18.26 Ask An Advisor With Wes Moss

2026-08-18

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What History Really Says About All-Time Market Highs & Should You Move to a 55+ Community? With the S&P 500 continuously hitting new all-time highs in 2026, many investors are wondering if the market has moved too far, too fast. In this episode, Wes Moss dives into the history of market highs, explaining why record-breaking runs are actually far more common—and far less dangerous—than headlines suggest. Also, Wes tackles one of the biggest lifestyle decisions in retirement: deciding where to live. Mai...

What History Really Says About All-Time Market Highs & Should You Move to a 55+ Community?

With the S&P 500 continuously hitting new all-time highs in 2026, many investors are wondering if the market has moved too far, too fast. In this episode, Wes Moss dives into the history of market highs, explaining why record-breaking runs are actually far more common—and far less dangerous—than headlines suggest.

Also, Wes tackles one of the biggest lifestyle decisions in retirement: deciding where to live. Maintaining a vibrant social circle gets harder as we age, but moving to an active 55+ community can provide the built-in social network, amenities, and lifestyle needed to thrive. Wes walks through a real-life case study of how to properly research, visit during peak seasons, and test-drive these neighborhoods before buying. Plus, he reveals a clever tax strategy for funding your next home without triggering a massive tax bill.

Mentioned on the show:

The Overlooked 'Rule of 55' Could Unlock an Earlier Retirement
A Simple Rule for When To Take Social Security

Plus, Christa shares your #AskWes questions and Wes gives his take. All this and more on the August 18, 2026, Ask an Advisor episode of the Clark Howard podcast. Submit your questions: WesMoss.com/ask

Discover the research-backed path to a happier retirement – pre-order The Retire Sooner Method by Wes Moss today at retiresoonermethod.com

We hope you enjoy our weekly Ask An Advisor episodes. Let us know what you think in the comments!

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