I'm deeply grateful for my career--never more so than when my 14-year-old son, Luke, tells me he's proud of what I do and wants to start his own business someday.

And while I worry about the innumerable heartaches that await him down that road, I couldn't imagine reacting to his early interest in following in my footsteps with anything other than enthusiastic encouragement.

To get him thinking earnestly about this particular journey, we recently sat down to come up with a list of qualities that go into making a great entrepreneur. It's an exercise that I figured would yield positive lessons for him--and the kind of good vibes that dads like me live for. So, after a few days of discussion, we finalized what I considered to be a solid screed of highly prized entrepreneurial principles: integrity, intelligence, curiosity, passion, optimism, and resilience.

I really liked our little creation, considering it a comprehensive summary of attributes that comprise a nearly invincible formula for success--in business or in life. In the immediate afterglow of our experiment, however, came the tragic suicides of Kate Spade and Anthony Bourdain--both bold and highly creative trailblazers who seemed to exude our entire catalog of world-beating qualities. And yet each of these glowing strengths proved helpless in the face of some opposing, obviously much more powerful force that led these extraordinary humans to opt out of the kind of life any dad would want for their child.

While I'm certainly in no position to guess at or judge the unknowable reasons that could lead someone to take their own life, the deaths of these two revered, successful figures made something immediately clear to me: the experiment I'd conducted with my son--while appropriate for a 14-year-old--was woefully inadequate as a full accounting of the requirements for the journey ahead of him.

During our time together, Luke and I spent hours admiring and contrasting the kinds of sunny, thoroughly mapped characteristics that make up the chapters of best-selling business books. The kind that get results, influence people, and win the day. But never did we discuss how to navigate the unlit and lonely caverns inevitably encountered on this same odyssey, which can make one doubt their abilities, question their purpose, and lose their will.

It's a darkness I know well--through my own experiences and those of friends in both business and personal circles. And the first step in confronting the problem is to acknowledge a seemingly paradoxical truth: that the companion of success and wealth is very often anxiety and depression.

For many of the high achievers I know who wage these ongoing battles, the root cause often involves their reality failing to match the picture of success they have in their heads. For some, it's because the vision they have for their life is much grander than the reality. For others, it's the opposite: they achieve their wildest dreams thinking it will provide some great answer missing in their life--only to realize they're the same person they were before, now saddled with a feeling of deep undeservedness.

Of course, I have no way of knowing whether such notions were a factor in the deaths of Anthony Bourdain or Kate Spade. But I know from my own entrepreneurial efforts that the mere act of choosing to blaze your own career path exposes you to sometimes crippling levels of disappointment and alienation. After all, the day-to-day of being an entrepreneur is far more gladiatorial than it is glamorous. You're stepping into a heavyweight fight and literally playing rope-a-dope with the world's problems, sometimes using every fiber of your being just to make it another round. And addressing such challenges often involves finding a place to park the horrible physics you face every day until you decide you have capacity to pull them out and deal with them.

I have entrepreneur friends who are like a hot knife through butter in their business lives. But if you peeked into the sidecar where they compartmentalize their fears and bottled-up emotions, you'd be terrified for them. No mental health expert would say that coping mechanisms like this are healthy, of course. But sometimes they're the only way you feel you can unburden your psyche enough to keep yourself and your mission moving forward.

I'd like to say I'm immune to this behavior; I'm not. The morbid truth is, I spent a significant period of my career in a quiet depression that was manageable only because I had a company to keep my mind off it.

A few years ago, though, this stopped working for me. Sick of being someone who could identify and resolve my company's root problems--but not my own--I started going to therapy.

Turns out, the core issue driving me was a complicated relationship with my father that fueled my ambition at the same time it torched countless other things it touched--most notably my health, relationships, and mental well-being. My need for constantly proving my worth no doubt powered some of my successes and blasted me through countless rejections. But all the while it was rattling around loose inside of me, slowly chipping away at the edges of my soul.

Recognizing this and striving to remedy it has turned into the most important work of my life. It means prioritizing my personal well-being alongside that of my company's. It means pursuing my passion knowing full well that success is no guarantee of happiness. And it means upholding a new set of business attributes to encourage openness and self-examination--for myself, others on my path, and those just beginning to consider it.

Published on: Jun 18, 2018