Why Even Wildly Successful People Are Vulnerable to Depression


This column first appeared on LinkedIn.

Kate Spade, that seemingly cheery fashion industry icon, wife, and mother who inspired millions of adoring fans, tragically took her own life last week, after years of battling with depression.

Spade is not the first entrepreneur to struggle through mental health issues. A 2015 University of California study said 49 percent of entrepreneurs suffer from some degree of mental illness, and the suicide of entrepreneur Jody Sherman in 2013 led many to see a connection between startup culture and mental illness.

Depression is complicated and messy and there isn’t enough information available to know precisely when her depression began or where her triggers lay, but it is said to have worsened in recent years. She had sold all of her interest in the Kate Spade brand by 2006; after a 10-year break, she and her husband, Andy Spade, launched the lesser-known Frances Valentine line, named for their daughter, Frances Beatrix Valentine Spade. The relationship between a founder and their business is fraught and fragile. In Kate’s case, it may have played a role in her depression.

So-called “successful” entrepreneurs — those who see an exit for their business — are a lesser-known segment of the mental health population. They are misperceived as “winners,” who have crossed the “finish line,” that goal in entrepreneurship of attracting a buyer and cashing out, free to sail off into the sunset. They no longer endure the pressures of the founder-CEO, relentlessly managing investors and revenue targets. For Spade, her success was financial — a net worth of $150 million — and influential: She had changed the game in handbags, forcing bigger players to create and market handbags in new ways. It’s hard for many people to observe such success and accept that it can manifest as pressures that become internalized and wreak mental and physical havoc on a person.

Markus Persson, the creator of the Minecraft games, sold his business to Microsoft in 2014 for $2.5 billion and was chided for his conflicting feelings. At first, he played the role of newfound wealth: beating out Jay-Z and Beyonce to buy a $70 million Beverly Hills mansion where he threw over-the-top parties with celebrities, and jetting off to places like Ibiza on a whim. But before long, he fell into a depression and took to Twitter to share that he had “never felt more isolated.”

In my conversations with dozens of founders for Exit Club, my project focused on the post-exit transition, mental stability after a transaction has been a key theme. “Regular bouts of depression,” more than one entrepreneur told me.

Why are successful entrepreneurs prone to depression?

Because you’re supposed to be happy.

Not long after I sold my own business last year, a friend said to me, “I don’t know why you’re not happier.” It was puzzling to me as well; we had worked hard on our media business and saw validation in our model when a buyer came along and scooped up the company. I no longer had the daily pressures of payroll, and my own paycheck was healthy.

One of the key beliefs in entrepreneurship is that you are to build a business toward an acquisition. This is the proverbial “finish line,” the big goal. But for many entrepreneurs, it doesn’t feel like a win, because what follows isn’t all unicorns and rainbows. It’s a hard adjustment to a new life.

“I have to try to not be negative when people ask how I’m doing,” says one entrepreneur who sold her business last year.

For those who have significant financial outcomes from the sale of their business, their problems are not relatable to most people in their lives, and that can be very isolating. One entrepreneur I spoke with said that friends became jealous; others expected a payout. What followed were a few years of literally staring at the nearby lake from his deck.

One’s own perception of oneself, of life, and questions around what to do next are thrown into a cauldron of confusion. Issues of identity and the value of things and the meaning of life–these are significant and hard to navigate alone. One entrepreneur burned through his $30 million gain because he viewed money as the problem; the founder of a massive software company became schizophrenic in the aftermath of the sale and his hallucinations ultimately proved fatal.

The post-exit period is a very lonely experience because of societal expectations that one should just be happy, and because there is no guide for how to manage through it. Lottery winners experience something similar in what’s been termed “sudden wealth syndrome.” Selling a business is that, and more.

Selling a business is a loss–and MRIs show it.

Even as your whole world is turning upside down, you are also losing a number of things that create absences in your life. A known change in financial status has caused several entrepreneurs to lose friends who were jealous or didn’t know how to relate to them anymore. Some marriages fall apart. Other unperceived losses are around fulfilling social needs that a job tends to do — having a place to go every day where you interact with people about important as well as totally meaningless things. A daily routine is gone, which really throws people off; and you can lose your clear sense of meaning and values with all the change.

You also lose your “baby.” Even the most burned-out entrepreneurs, ready for a break from the grind, go through a period of mourning, and it’s no surprise: a 2017 study by the University of Helsinki used MRI scans to show that entrepreneurs are attached to their companies in the same way parents are to their children.

Second businesses aren’t anything like the first.

“The expectations are higher now,” Andy Spade told Fast Company in 2016. “So we have to make a great product, and then we’ll build out the company.”

Starting a second business can hold demoralizing surprises for entrepreneurs, and these may have befallen the Spades. Circumstances under which company No. 1 was started can be radically different. For Kate Spade v. Frances Valentine, not only did fashion tastes and consumer habits shift in the 23-year period, but the introduction of social media makes for a far different marketing landscape than in 1993, when print magazines and billboards were largely the tool of choice for fashion advertising.

Entrepreneurs who successfully sell their businesses may worry about whether they were just lucky the first time around, and the fear of failure can be debilitating. They also have greater expectations of success and access to capital and resources, and these may be just as hard to come by as the first time around. One entrepreneur I spoke with in depth talked about the relief after selling his business and expectation that he’d jump right into the next one. Instead, three attempts failed to take hold and he fell into a deep depression. He didn’t leave his bed for days, and his live-in girlfriend eventually moved out. Starting a business is difficult, and succeeding once doesn’t guarantee that it will be any easier the next time; many entrepreneurs are surprised to discover this.

Post-exit transition needs to be acknowledged.

To be sure, these are first-world problems, but problems nonetheless, with impact on the lives of real people — not just the entrepreneurs but also their families: their spouses, their 13-year-old daughters.

The potential for a fulfilling post-exit life exists, but it eludes many because they don’t prepare for it. If you plan to sell your business, spend a lot of time planning for your life that follows. Identify a support group you can turn to as you hit the inevitable bumps. The most important thing is to ask for help, and Exit Club exists in part because successful entrepreneurs need a safe space to connect with others who have had similar experiences, and know they can make it through.

Mental health is an issue for everyone. Even successful entrepreneurs.