Sell in May and Go Away? Wes Moss Says $1 Grew to $20 Instead of $41
Wall Street's oldest seasonal rule sounds sensible until someone actually runs the numbers across 36 years of market history and puts a specific dollar figure on exactly what calendar-based investors left behind.
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.
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.
The appeal is easy to see. The rule is simple, it runs on the calendar, and it promises a way around the scary volatility that often shows up in late summer and autumn. It also gives anxious investors something to do, which can feel better than sitting through a decline.
Why Sitting Out Half the Year Costs So Much
By Wes Moss’s figures, a dollar run through the Sell in May approach grew to 20 bucks. Wes Moss said the same dollar left invested the whole time grew to 41 bucks.
Compounding explains most of that gap. Any gain you miss over the summer also reduces the base that grows each year after that. Stretch that over more than three decades and the missing months pile up. Timing also has practical costs. In a taxable account, each spring sale can trigger capital gains taxes, and selling on a schedule means you’re out of the market for any strong rally that lands between May and October.
Retired people have the Most Riding on This Choice
Older Americans now own a large share of the stock market. Federal Reserve Distributional Financial Accounts data show that households headed by someone 70 or older held 40.5% of all household holdings of corporate equities and mutual funds in the second quarter of 2026. That compares with 39.8% in the first quarter and 17.6% in the first quarter of 2009.
Retirement portfolios may also have to do more of the work in the years ahead. The 2026 Social Security Trustees Report projects that the combined OASDI trust funds will run out in the third quarter of 2034. After that, 83% of scheduled benefits would be payable. A retired person who sits out half of each year’s market gains has less protection if that shortfall happens.
A Smarter Plan Than Stepping Aside
Retired people usually want to time the market because they fear having to sell stocks during a crash to pay their bills. A cash buffer deals with that fear head-on. Many planners suggest setting aside a few years of expected withdrawals in cash, Treasuries, or high-quality bonds and keeping the rest invested for growth (we walked through why those first few withdrawal years matter so much, and how to defend them, in a free guide on sequence-of-returns risk).
When stocks fall, retirees spend from the buffer and leave the stock holdings alone to recover. Once markets rebound, stock gains can refill the reserve. With that setup, the calendar stops mattering, because near-term spending no longer depends on what stocks do in any particular season.
What Investors Should Check Before Year-End
November is when Sell in May followers usually get back into stocks, which makes it a good time for a checkup. Investors can review whether a reserve still covers the next few years of planned spending, whether a year of market moves has pushed a stock allocation away from its target, and whether a set rebalancing schedule fits their plan. By Moss’s numbers, the investor who stayed in the market turned a dollar into 41 bucks, while the calendar timer ended up with 20 bucks.
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Chris Lange is a financial and geopolitical writer with more than a decade of experience covering a myriad of topics. He has published thousands of articles for 24/7 Wall St., with past coverage focused heavily on stocks, IPOs, healthcare, defense, global affairs, and technology.
His work has been quoted, or referenced by a number of outlets including Business Insider, USA Today, Yahoo Finance, MSN, The Motley Fool, and many other publications. A graduate of Southwestern University, he studied business with a focus on investments and has previous experience in banking and startups.
When not reading or writing the news, he is following his passion for Lacrosse, playing chess, or building solar projects with his dad.
