The Road Not Taken
“What if” hurts more than “oops”
The human experience is paved with choices, big and small. But it’s often the decisions we don’t make that cast the longest shadows.
This is a central theme explored in Kazuo Ishiguro's novel Remains of the Day. The story follows Stevens, a butler who sacrifices his personal life for his employer. In his twilight years, a haunting realization dawns on Stevens: a life lived cautiously, devoid of passion, is a life barely lived at all.
Inspired by Remains of the Day, Jeff Bezos developed what would become his signature decision-making approach: the Regret Minimization Framework.
The core principle is simple: When looking back at the end of your life, which decision would cause the least regret? For Bezos, the answer became clear. The real risk wasn’t in failing but in never attempting — in allowing fear to calcify dreams into unexplored potentials.
Bezos left behind the comfort of his Wall Street career to chase the uncharted territory of the internet, founding what would become Amazon.
St. Ignatius described a similar exercise for decision-making in the Spiritual Exercises nearly 500 years ago. He was also not afraid to make bold decisions.
After crisscrossing Europe for many years, Ignatius, “the pilgrim,” spent roughly fifteen years at a simple desk in Rome directing the nascent Society of Jesus.
At the end of his life — which took place a few steps from that desk — Ignatius could see that he had continually sought the greater glory of God. More was not possible.