5 Leadership Tips From John F. Kennedy’s Darkside


Forget the bold words and speeches of John F. Kennedy. Let’s look at his actions. John F. Kennedy undoubtedly holds an allure over Americans as the young, attractive Catholic that presided over “Camelot” and fought for the ideals of a new generation. But his dark traits have also been well established over the last 40 years. Surely we can learn from his speeches and his noble characteristics. That isn’t hard to do. But I think he “dark side” offers some valuable lessons as well. What made him a dangerous President can also make you a stellar leader, if you apply these traits reasonably. Remember: those who can’t learn from the bad in life are missing half of life’s lessons.

Here are 5 positive takeaways from the dark side of John F. Kennedy:

1. Be Willing to Take Risks

“Those who dare to fail miserably can achieve greatly.”- John F. Kennedy
It was his defining characteristic. From the Bay of Pigs to Marilyn Monroe, JFK liked to risk shit. He liked to live on his toes. His sexual escapades continually disrupted national security (not to mention his own marriage), and his apparent recklessness brought us (arguably) close to World War III. Apparently, he once slept with a lover in the Georgetown home that he shared with his wife and children the night before his inauguration. As evil as some of his actions may have been, taking risks is important. Today, as an entrepreneur, artist, or anyone looking to make a difference, risk is inevitable. One cannot crawl through life avoiding misfortune and danger. Instead, to forge new paths, one must be willing to travel past everyone else’s worn out paths. As Tim Ferriss says,“What we fear doing most is usually what we most need to do.”

2. Take Advantage of Resources

John F. Kennedy was blessed, in a myriad of ways. His father, a controversial figure himself, was purportedly one of the wealthiest men in America in his time. It was also suggested that he earned most of his money during, and after, prohibition, both illegally and legally importing liquor to America. Whether this is true or not doesn’t matter. Both Joe Kennedy and his son knew how to exploit the resources they had, sometimes not so morally. We’re not all born into wealth or status, but we certainly all have our blessing and resources that we’ve compiled over the years. Use them and use them strategically. This isn’t limited to money. JFK was physically ill his whole life. In fact, he was given his last rites 3 times before he was forty years old. So while his physically healthy brothers were active and athletic, Kennedy read and studied, developing his aloof and intellectual demeanor. It’s also been speculated that Kennedy used his mafia connections to gain early intelligence of the Bay of Pigs situation in Cuba. Here’s the lesson: Take advantage of what skills, money, and connections you have available in your own life. And at the same time, if you’re running a business, take advantage of the fans/customers you already have before seeking additional clientele. They are your best marketing device.

3. Turn Negatives into Positives

“The Chinese use two brush strokes to write the word ‘crisis.’ One brush stroke stands for danger; the other for opportunity. In a crisis, be aware of the danger–but recognize the opportunity.” – John F. Kennedy

John F. Kennedy was a frail and physically weak child. He also had a slight feminine manner. Robert Greene says that because he capitalized on these weaknesses, he was successful. Had he overcompensated, as do many people, he would have only showed his insecurity. At the same time, while running for President, Kennedy was young. And Catholic. He used both of these supposed negatives to his advantage. With his youth, he rallied a new generation against the old complacency of Eisenhower’s 1950’s, and he inspired them with imagery of the American Frontier. As our only Catholic President, he made a direct appeal to anti-Catholicism, displaying both confidence in his capacity and alleviating American’s anxieties about having a Catholic President.This one is a tenet of stoicism. As Tucker Max says “Obstacles are only obstacles if you see them as obstacles. They can also be called opportunities.” You can always choose to view negative situations as that. But if you cannot control the situation, then you can at least control your reaction to it. And you can make your reaction to it positive.

4. Stop Complaining and Arguing, Seduce and Inspire (Connect with People)

Most of Kennedy’s allure stems from his legendary charisma. His bedroom escapades are, at this point, almost folklore in their quantity and drama. But let’s not forget that his same manner of communication he used in his affairs, he used to seduce a nation. In personal affairs, he had been described as someone who would never complain, which is substantial considering his physical suffering and back pain. On a national level, he provided the same allure. He gave the American citizens an image of hope, chivalry, and a rich future. He connected with them on their cold war insecurities and on their diminishing post war comfort. His speaking was elegant. The Great Debates for the 1960 election are always conjured when reviewing recent American History. For the nation’s first televised debates, Kennedy trained himself to look at the audience, speak positively, and use emotion to communicate his message. Richard Nixon was said to be sweaty and anxious, although his radio audience appreciated his use of facts and his deep voice. As James Altucher says, “Arguing with people is like reading your email at 4 in the morning. There is absolutely no good that can come of it. It’s just scratching an itch.” Take this to heart in both your business management and personal skills. Arguing won’t bring people to your side. It will make them defensive and less likely to be persuaded. Dale Carnegie wrote about this. Learn to connect and engage instead of arguing.

5. Keep Fucking Moving (Persist)

“Do not pray for easy lives. Pray to be stronger men.” -John F. Kennedy

The biggest lesson, and the one that ties it all together, is that Kennedy was persistent. JFK had a deep base of insecurities, failures, and personal baggage. You can call it ambition or persistence or whatever else, but he kept moving. In his frail youth, he stayed alive. That was a major feat, given his Addison’s Disease. He struggled with his health his whole life, but neither complained nor stopped moving. It wasn’t just his health. Khrushchev beat his ass in a debate over Berlin. Bay of Pigs was a famous failure. Time and time again, Kennedy fucked up and embarrassed himself, but kept moving. You can do the same. You’re (likely) not making major decisions on international diplomacy or dealing with the threat of impending nuclear war. Take risks, and learn from your fuck ups. Don’t stop moving; keep going.

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