Andrew gets to pick when he retires — but not what the market did on the way in. Here's every real (inflation-adjusted) S&P 500 return he could have retired into since 1940, measured over how long he'd been invested.
Trailing real return, by years invested
After inflation · monthly, 1940–2026 · dividends reinvested
Chance of clearing a real return hurdle, by years invested
Share of all months since 1940 whose trailing real return met or beat the hurdle
Robert Shiller's monthly S&P Composite dataset (shillerdata.com), total return with dividends reinvested, deflated by CPI. Charts and stats cover windows ending January 1940 or later; the windows reach back as far as 1890, so every point is a full-length hold. Past returns don't promise future ones.