Smoothing Life’s Uneven Road by Preparing in Calm Times

Back in ’65, Captain James Stockdale parachuted into enemy territory and was immediately captured. A Medal of Honor recipient later reflected that his true survival strategy wasn’t courage under torture but simple preparation before it even began.
In peacetime, Stockdale studied Epictetus. He ran mental drills: imagining the worst, rehearsing calm speech, plotting secret codes. When real torture came, he was alarmed but not broken. He knew how to bear it.
Business is no less unforgiving. Markets crash, regulators shift rules, competitors pounce. At a fintech startup, the team set aside one week a quarter to furlough the system—forcing everyone to handle customer support, pricing plans, and investor pitches on paper.
They found new efficiencies, uncovered hidden vulnerabilities, and emerged more confident. It wasn’t fun, but it made them battle-ready for actual outages and market shocks. Today they boast 99.99% uptime and resilient cash flows.
Whether you’re leading a company or your own life, winter drills in calm times are a cornerstone of the Stoic approach.

You pick today’s “winter drill,” remove a comfort or introduce a surprise, then treat it as a real crisis—respond calmly, test solutions, and log what saved you. These intentional tests replicate Epictetus’s drills. After, you’ll find the actual storms won’t knock you off your feet.