Why Timing the Market Is Hard
Why stepping out of the market before bad times and back in before good times is so much harder than it sounds, tested against nearly a century of US returns, and what long-term investors do instead.
The short version
Market timing means moving in and out of investments based on predictions about where prices are headed. It requires two correct decisions, when to get out and when to get back in, in markets where short-term moves are extremely hard to predict. In US data from 1929 to 2025, simple timing rules did worse than staying invested: moving to cash for a year after every losing year cut average growth from about 9.7% to 7.8% a year, partly because five of the ten best years came right after a losing year. Perfect timing would have helped enormously, but nobody can count on it. Staying invested with a sensible mix, and rebalancing, has been the more reliable path.
By the end of this lesson, you'll be able to
- Explain why market timing requires two correct decisions
- Describe what simple timing rules and missed best years did to long-run returns in US data
- Describe the alternatives long-term investors use instead of timing
Why this matters
After everything in this module, recessions, bear markets, bubbles, a natural thought is: why not simply step out before the bad times and back in before the good ones? It's the most tempting idea in investing. This lesson tests it against the data, and the results explain why most long-term investors don't try.
Two decisions, not one
To time the market successfully, you have to get out before a decline and get back in before the recovery. Getting only the first one right isn't enough: selling before a 30% fall is wasted if you buy back in after a 40% rebound. And both decisions have to be made in real time, usually amid alarming or exciting news.
The research recognized by the 2013 Nobel Prize in economics found that there is no way to predict stock and bond prices over the next few days or weeks, although the broad course over several years is somewhat more predictable.1 Most timing decisions are about the short term, which is exactly where prediction is hardest.
Testing it on nearly a century of data
Using yearly S&P 500 returns, including dividends, and 3-month Treasury bill returns from Damodaran's data,2 here's how some timing approaches compare with simply staying invested from 1929 to 2025:
| Approach | Average yearly growth |
|---|---|
| Stay invested the whole time | 9.7% |
| Move to Treasury bills for a year after every losing year | 7.8% |
| Miss the 5 best years, in Treasury bills instead | 7.7% |
| Miss the 10 best years, in Treasury bills instead | 6.2% |
| Skip the 5 worst years, in Treasury bills instead | 12.3% |
Calculated for this lesson from yearly data, before fees and taxes. "Average yearly growth" is the compound rate. Yearly data can't capture moves within a year.
The table shows both sides honestly. Skipping the worst years would have been wonderful. But the simple, rule-based attempt to avoid trouble, stepping aside after a bad year, cost almost two percentage points a year, compounded over a lifetime. The reason is that good years tended to follow bad ones: five of the ten best years in this period, including 1933, 1954, 1958, and 1975, came right after a losing year.2 Investors who stepped aside after the losses were out of the market for some of the biggest gains.
The rest of this lesson is for members
Still to come in this lesson: The evidence from real investors, What long-term investors do instead, the key takeaways, and 2 quiz questions with explanations.
Membership opens every lesson in the curriculum, the capstone projects, the interactive tools, and the members-only channels in the Hyperion Entities Discord. The first lesson of every module stays free.
Go deeper
- Dollar-Cost Averaging, Lump Sum, or Scaling In?Part 5: Building a Portfolio
- Passive vs. Active InvestingPart 6: Strategy, Behavior, Accounts, and Taxes
- Portfolio Drift and RebalancingPart 5: Building a Portfolio
Notes and sources
- Nobel Prize Outreach. The Prize in Economic Sciences 2013: Press release. Checked 2026-10-05. Back to text
- Aswath Damodaran, NYU Stern School of Business. Historical Returns on Stocks, Bonds and Bills, with annual data through 2025 (updated January 2026). Checked 2026-10-12. Back to text
- Morningstar, Portfolio and Planning Research. Mind the Gap 2025 (August 13, 2025). Checked 2026-10-06.
- Vanguard Research, Megan Finlay and Josef Zorn. Cost averaging: Invest now or temporarily hold your cash? (February 2023). Checked 2026-10-05.