How I Failed at the Most Important Part of Being a CEO

For years, my 360 reviews detailed a short-attention span, an inability to pay full attention to my employees in one-on-ones, and a contagious anxiety.

I’ve been wandering my way through Carl Jung’s autobiography, and he said something that brought to the surface an idea I’ve been carrying for several years now. The idea arrived in my life first in my role as CEO of a venture-backed startup. My coach, Jerry Colonna, challenged me with the idea:

If you want to be a great leader, you must start by learning to manage your own psychology.


I’m going to bastardize Jerry’s lesson, but what I took from it was an understanding that if I was going to be the leader my team required, if I was going to show up for one-on-ones able to hold space for my reports, to sit in strategy sessions with real clarity and curiosity, and explore our customers and our market with an open mind, I was going to need to first learn to manage my own head. My insecurities, my anxieties, my self doubts would need to be waylaid as best I could manage, and the better I learned to manage the greater my odds of success as a leader.

Leaders who don’t learn to manage their own psychology first inevitably dump their issues on their teams:

• They show up for meetings with their own fear anxiety echoing so loudly in their minds they can’t possible hear anyone else clearly

  • They have short tempers
  • Their teams find they are never really listening to anyone around them
  • They evidence a desire to jump to quick answers, in order to experience psychic resolution, instead of unpacking complex problems.

I should know. This was how I led for my first several years as a founding CEO. Dozens of people can attest to that fact sadly.

Over the years, I’ve learned the skills to begin to understand how to tap into my own mind, my subconscious, and my well-being. I say begin because this is an every day practice.

My daily practices around managing my own mind include:

• Kicking off the day with meditation (10 min) and journaling (typically in the 5-minute gratitude journal format)

• Frequent breaks for walks (targeting 10k steps per day)

• Evening meditation (10 min) and journaling to reflect on and unpack the day (if I’m wiped out, these practices are sadly too often skipped for TV and sleep)

My weekly practices also include:

• Weekly meetings with a cognitive-behavioral therapist I’ve worked with for 7 years now

• Bi-weekly meetings with a coach

What’s surprised me most about this path of learning about my own psychology is the realization the same practices is necessary and the same benefits realized in my roles outside of work. Hands-down the hardest and most critical part of being a father is ensuring I show up for my time with my son with a mind at rest and an open heart. That can be fucking hard after a day running a company, or a day where any of the other adult life stresses fill my mind. But when I get it right, when I do my morning practice before he wakes up and show up ready for a morning game of Uno ready to be present with my son and deeply enjoy him, the experience is magical. For both of us. The difference in him is palpable, he’s happier, more at ease, and more helpful when he feels connected to my wife and I because we’ve shown up ready to connect with him.

Trying to get it right for this little guy.

That’s parenting, but I’ve seen the same experiences born out in my relationship with my wife and in my friendships. Showing up with my mind at ease and with intentionality about the time shifts the connection and the time spent together.

I love Jung’s quote about this topic. He’s talking about his training of new psychologists and the critical importance for each of them to do their own work first. It’s not enough to learn the craft, to study the science of the human mind and learn how to care for patients:

You yourself must be the real stuff. -CG Jung

I love that. I love it applied to psychologists. I love it applied to friendship. I love it applied to marriage and parenthood. And I love it applied to leadership.

It’s fucking hard. It’s hard work to learn to be the real stuff. For me it’s meant letting go of the things that made me feel better for much of my life without actually making me better. Perfectionism. Workaholism. A facade of having it all figured out and being too cool to care. It’s hard for me to let go of these things because they have served me in certain ways. My work ethic enabled me to find my own way financially to separate from a childhood family dynamic that wasn’t healthy for me as a 20-year-old. My perfectionism drove me to excel at college and graduate school and opened up doors to the career I now experience and love. But those gods no longer serve me. They don’t allow the life I know long to live. And I’m still honestly grappling with how I live and work without them. Rather than acting like I have that figured out, I’m trying my best to show up in friendships, conversations and writing with honesty about the exploration.

Letting go of that way of being challenges my sense of who I am at my deepest levels.

For me, this question, and other questions like it I’m carrying, are at the core of the ongoing work of learning to know, manage, and care for my own psyche. The daily and weekly practices are very helpful, but the effort is decades long not an overnight fix. And even years in, I feel I’ve only just begun.

The good news, I’m learning I believe, is the exploration of these questions, questions of what defines us as people, how we can most deeply relate to others, and by which gods we want to be driven in life, this exploration is the foundation of the greatest adventure in life. At least the greatest adventure I’ve found so far in a lifetime of adventure-seeking. Wherever you are today in your own adventure of self-knowledge, I’m wishing you peace and community.




Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store