Will You Regret It at Eighty Years Old

When Jeff Bezos was a vice-president on Wall Street, he asked himself, “When I’m eighty, will I wish I’d stayed?” The answer led him to quit his secure job, borrow money from his parents, and drive cross-country to start Amazon from his garage. That mental test gave him clarity beyond any spreadsheet.

A decade later, entrepreneurs at a small software firm tried the same experiment. One senior developer imagined himself offering his e-commerce app on his deathbed—he saw regret in leaving it unlaunched. He scheduled a weekend hackathon, built an alpha, and discovered a community of early adopters. That small “regret test” perspective shift unlocked six-figure revenues.

Psychologists call this “temporal self-projection,” where envisioning your future self can override present fears. It combats “present bias,” our tendency to favor short-term comfort over long-term fulfillment. By literally time-traveling in your mind, you align daily actions with decades-ahead values.

In both stories, the future-regret question cut through a tangle of excuses—lack of time, fear of failure, or wanting perfect conditions. The result was fast, decisive action grounded in enduring purpose.

Use the Bezos Regret Test yourself: picture your legacy at eighty, note what you’d mourn, and then set your first meaningful step this week. It’s more powerful than any to-do list.

Imagine your eighty-year-old self smiling on your birthday, then list the dreams you’ve been deferring and rate how much you’d regret never starting each. Finally, pick the highest-regret item and calendar your first step before Friday. Give it a try tonight.