Quick Read
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Wes Moss found that staying fully invested from 1989 to 2025 grew $1 to $41, while followers of “Sell in May” only reached $20.
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Compounding drives the gap: missed summer gains shrink the base that grows every subsequent year, and spring sales trigger capital gains taxes.
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Households headed by someone 70 or older now hold 40.5% of all household equities, making this the highest-stakes decision for retirees.
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Every spring, the old Wall Street saying “Sell in May and Go Away” returns. Every fall, nervous investors wonder whether they should have followed it. Wes Moss has now put a price tag on that question. On the October 27, 2026 “Ask An Advisor With Wes Moss” episode of The Clark Howard Podcast, Moss walked through data on the saying covering 1989 through 2025. The gap he described is big enough to change how retired people think about stepping aside when markets get scary.
Moss said: “If you sell in May and go away, a dollar grew to 20 bucks over that period. If you were invested the whole time, it grows to 41 bucks. It’s pretty obvious timing the stock market doesn’t hold water.”
Moss is a CERTIFIED FINANCIAL PLANNER® and serves as managing partner and chief investment strategist at Capital Investment Advisors, a fee-only SEC-registered investment adviser with over $8.1 billion in assets under management. He hosts the Money Matters radio show and the Retire Sooner podcast, and he appears regularly on Clark Howard’s show. Past episodes are available on Clark Howard’s official podcast page.
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What “Sell in May and Go Away” Actually Means
In plain terms, the strategy tells you to sell your stocks at the start of May, keep the money in cash or other safe assets through summer and early fall, and buy back in around November. The idea rests on a belief that the May through October stretch has historically been the weaker half of the year for stocks.
