Working at Forbes is a licence to learn from the successful. I like trying to crack the code of long-term successful people who also enjoy fulfilled and satisfying personal lives. Warren Buffett fits that description. So does Bill Gates. Steve Jobs was getting there, after a brilliant but tortured start. Jobs once scandalously denied paternity of his daughter Lisa. The later Jobs reconciled and became a devoted father. It can’t be coincidence that the reconciled Jobs was a far better leader and manager.
Evolving people are worth studying, such as Elon Musk, defeating his demons as he becomes more successful. The one-hit wonders (Jobs before his renaissance) are also worth studying but mostly as cautionary tales. Allow me to make a sweeping and general comment: People who enjoy long-term success, along with deep personal fulfillment, are terrific at regret avoidance and mitigation.
The word ‘regret’ conjures the pain of sin and the embarrassment of foolish mistakes. Everyone who isn’t a sociopath—they can achieve success, too, but at a price healthy people would rather avoid—will suffer regrets from sins and stupid mistakes. We cheated. We destroyed a rival with gossip. We told a joke that shamed a colleague. We harmed our children. Left unaddressed, these kinds of sins and goofs pile up and rot us.
Long-term successful people sin and err but know the soul toll will keep compounding, so they learn to make fewer sins and errors. British magazine publisher Felix Dennis played rough in business and masked the guilt he felt with cocaine and booze. Toward the end of his successful career and, sadly, his cancer-shortened life, Dennis wrote his book How to Get Rich in which he expressed his regrets. He quit the coke, cigarettes and heavy boozing. His reconciling life mission at the end, besides writing his candid books and poetry, was to plant a beautiful forest that would delight future generations.
The long-term successful acknowledge their mistakes and seek correction. This might be by asking forgiveness in a traditional religious way. It might be in therapy or 12-step groups. It might be in pay-it-forward gestures of Dennis’s type. But the regrets of sin and error must be dealt with, or they will grow like fungus and damage their host.
The worldly successful—because they tend to be alpha people who enjoy the thrill of adventure—are actually more prone to making avoidable errors. Babe Ruth swung at many bad pitches, pitched many women and ate a lot of bad food. My friend Cameron Herold, the famed CEO coach, points out that entrepreneurs are more bipolar than non-entrepreneurs and are thus more vulnerable to Ruthian screw-ups, from sex to gambling. Successful alphas are wise to visit the confessional—or the secular equivalent of their choosing—early and often if they want to make their success long-lasting and fulfilling.
Worse: Passive regret
But there’s another kind of regret, which alphas avoid better than people of lesser success: The regret of missed opportunity. Alphas don’t hesitate to take chances. The less successful watch, sit on their hands and tell themselves they are sober and wise in their decision making.
But regrets of passivity ruin lives, too. The Huffington Post in 2012 published a piece called ‘The Top Five Regrets of the Dying’. Here they are: