All The Cool Leaders Do It

In the late 1950s, America was in the midst of a Cold War with the Soviet Union. Tensions were high, and the stakes were even higher. One man found himself at the center of it all: President John F. Kennedy. Just a few months into his term, Kennedy faced one of the most significant challenges of his career—the Bay of Pigs invasion. The operation was a complete failure, resulting in a public relations nightmare and leaving the U.S. at a disadvantage in the Cold War chess game.

But something changed in Kennedy after that debacle. He began a series of private meetings, not just with his advisers but also with scholars, historians, and even critics of his administration. He poured over historical case studies, took copious notes, and posed endless 'what-if' scenarios. It wasn't just about gathering data; it was about absorbing the essence of each situation to better understand his role in it.

When the Cuban Missile Crisis erupted in October 1962, Kennedy's newfound approach was put to the test. Faced with the terrifying prospect of nuclear war, Kennedy opted for a different route than many of his military advisers suggested. He chose a naval blockade over immediate airstrikes against missile sites in Cuba. His decision was not just based on maps and charts but on a nuanced understanding of human behavior, historical context, and the potential consequences of each available action. He didn't simply lean on his advisers; he led them, pulling insights from the wisdom he had gathered from his past failures and contemplative exercises.

The Cuban Missile Crisis was peacefully resolved, and the world exhaled a sigh of relief. But for Kennedy, the crisis was also a personal milestone. Gone was the young, inexperienced leader who stumbled into the Bay of Pigs disaster. In his place stood a man with a much deeper, nuanced understanding of the intricate tapestry of leadership.

Kennedy continued to seek out new perspectives and question his own assumptions until the end of his days, shaping his approach to leadership in a way that left a lasting impact on American history. His transformation shows that sometimes, the greatest lessons come not from our successes but from our failures, and from our willingness to dig deep, ask questions, and listen—not just to others, but also to the untapped wisdom within ourselves.