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The Last Days of Tony Hsieh

Tony Hsieh, the charismatic former CEO of online shoe retailer Zappos, recently died tragically at the age of 46.

I had actually met Hsieh personally. Like everyone else, I thought he was a really great guy.

But one of the tragic realities of the human condition is that many of those who have the gift of touching others in powerfully positive ways are ones with serious personal wounds and problems themselves.

Hsieh was one of those people. He long seems to have had problems with drugs and alcohol, but those grew worse during Covid-19. And he also began experimenting with bizarre diets and other strange things.

At the end, he had entirely surrounded himself with Yes men whom he had paid twice as much as their previous lifetime high salary just to hang out and pursue “happiness” with him.

He cut off his old friends, and when one of them, the singer Jewel, did come to visit him and his lackeys in Park City, UT, she wrote him a letter – the only way to reach him – warning him that he was in trouble.

She wrote, “When you look around and realize that every single person around you is on your payroll, then you are in trouble.”

Let that be a lesson to us all. We have to make sure we always have people in our inner circle who have the standing to call us out and speak difficult truths into our lives.

Surrounding ourselves only with those who affirm us can be deadly.

Hsieh also shows the perils of failing to mature in life. According to Forbes:

Over this period, many of Hsieh’s longtime peers found themselves on a divergent path from him. “Each of us had to admit we hadn’t seen much of him lately,” says one venture capitalist who knew him for more than a decade. “And even if we saw him at TED, he would skip the talks and host the late night. Whereas we would be in bed by 9:30.” Nick Swinmurn, whose idea Hsieh transformed into Zappos, said that he had fallen out of touch with Hsieh and not spoken to him since last year. Their definitions of happiness had changed—a feeling echoed by several Hsieh friends, who said that they had married and started families, while Hsieh remained an extremely rich Peter Pan. “He told me that his friends kept getting younger and younger,” Swinmurn wrote in a Medium memorial post. “He seemed excited about this.”

Hsieh’s failure to embrace the satisfactions of mature adulthood undoubtedly contributed to his unhappiness and downfall.

The single life of partying and “happiness” is fun in your 20s and 30s. But the single life at 40+ is a very different reality.

Many single men and women in their 40s and 50s are far unhappier than they let on publicly.

Also, the lives of married people and singles fundamentally diverge at this time, as the article reveals.

People who stay single might imagine they’ll remain socially close to their friends who got married and had kids, but it usually doesn’t work out that way.

Men and women with families usually start to diverge from their single peers, and by their 40s and 50s, those who are still single end up in a singles ghetto with others like themselves.

Family life is not for everyone. But many people who miss the runway to it in their 20s and 30s end up much unhappier than they ever imagined they would.

If you are still younger, you must take this risk into account as you live your life today. But sometimes it’s too or very difficult to change course if we end up in a place we never thought we’d be.

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