Even the Worst Possible Market Timing Beats Staying in Cash

Meet the unluckiest investor in history. Fund Manager Vanguard calls him Unlucky Steve.

He invested $10,000 in a diversified global equities portfolio just before the dotcom crash in 2000. Then another $10,000 immediately before the GFC in 2008. Then a final $10,000 right before COVID in 2020. The worst timing imaginable, three times running. Between those entry points: September 11, the Iraq War, Enron, European debt crises, US credit downgrades, a pandemic, and years of recession fears.

Steve held through all of it.

By the end of 2025, his $30,000 had grown to $117,017 — a return of 7.6% per year. Had he stayed in cash? $54,165, or 3.4%. Over 30 years to June 2025, Australian shares returned 9.3% annually, US shares 10.8%, and global shares 8.3%. Even Australian listed property and fixed income provided 8% and 5.5% respectively.

The maths is unambiguous. The psychology is harder — because staying invested when markets are falling feels reckless, even when the data says otherwise. That’s the gap between knowing and doing. Every crisis feels unprecedented in the moment. In hindsight, every recovery looks inevitable.

What Vanguard’s analysis really shows isn’t just that time beats timing. It’s that the cost of waiting for certainty is almost always higher than the cost of being early. The best and worst trading days tend to cluster together — often within the same week. Miss the recovery and you lock in the loss.

The real challenge is ensuring your portfolio is built to withstand natural volatility by focusing on what you can control: clear goals, appropriate asset allocation, broad diversification, discipline, and low costs. It’s one of the reasons we build portfolios designed to stay invested through volatility rather than trying to time around it.

→ Our read: The risk most people worry about is buying at the wrong time. The risk that actually costs them is never buying at all.