AI Summary
5 min readThe stock market has been hitting a series of all-time highs in 2026, and financial advisor Wes Moss wants investors to understand what that actually means. He opens by pointing out that the S&P 500 closed at a new record level more than two dozen times so far this year, following a strong run in 2024 and 2025. There were zero all-time highs in 2023, which makes the recent cluster feel unusual. But Moss argues that history shows all-time highs tend to come in clusters, not as isolated events that signal an imminent crash.
He offers a specific historical example: a five-day stretch in late July and early August 2026 where the market posted a 99th-percentile move to the upside—meaning it was better than 99% of all five-day periods going back to 1950. The natural worry is that a market that just shot up 6% in five days is due for a correction. But Moss says the historical data points the other way. Over the next six months following such rare upside moves, the market has averaged gains of nearly 11%, compared to a typical 4% average over any six-month period. "The new all-time high doesn't at all historically say we're doomed for correction," he says. "It usually points to further momentum."
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What you'll learn
- 1 (01:05) **Introduction & Market Volatility Concerns** - Krista and Wes set up the show and address listener anxiety about recent market highs and a potential correction.
- 2 (02:20) **All-Time Highs: Are They a Warning Sign?** - Wes explains why a series of new all-time highs is actually a normal market pattern, not a signal of an impending crash.
- 3 (03:52) **The 1% Move and What History Says** - Wes analyzes a rare, top-1% five-day surge in late July/early August and explains its historical implications.
- 4 (09:49) **Early Retirement Case Study: Chris in Texas** - Wes evaluates a couple in their early 50s with $3.2M in assets who want to retire in 3-4 years.
- 5 (14:53) **The Healthcare Bridge in Early Retirement** - Wes addresses the specific concern about paying for private health insurance before Medicare eligibility.
- 6 (16:17) **When to Disclose Wealth to Adult Children** - Wes advises a parent (Kirk) with $10M net worth on how and when to tell his three high-earning adult children.
- 7 (19:15) **529 Plan Strategy for Private School** - Wes answers a New York resident’s question about using a 529 plan to pay for K-12 private school tuition.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
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!
Learn more about Wes:
Learn more about your ad choices. Visit megaphone.fm/adchoices
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