“When We Fail in Some Way or Another, We Can Simply Begin Again”

Portrait of Jerry Colonna

Jerry Colonna has had a very interesting career. He is a well-regarded venture capitalist, and as an executive coach, he’s helped many people do their best work. He’s the cofounder and CEO of Reboot.io, an executive coaching and leadership development firm.

If you listen to the terrific podcast Start Up, in Season 4, Episode 3, you may remember hearing from Jerry Colonna. Gimlet co-founders Alex Blumberg and Matt Lieber talked to him to help them work through some issues they were having.

And recently, Jerry Colonna’s new book has hit the shelves: Reboot: Leadership and the Art of Growing Up. From the description: “Reboot is a journey of radical self-inquiry, helping you to reset your life by sorting through the emotional baggage that is holding you back professionally, and even more important, in your relationships.”

I couldn’t wait to talk to Jerry about happiness, habits, and productivity.

Gretchen: What’s a simple activity or habit that consistently makes you happier, healthier, more productive, or more creative?
Jerry: One day last year I was stopped at a crosswalk while I was walking to dinner with my friend and teacher Sharon Salzberg. I told her, “You know; I’m happy. I’m sustainably, generally, happy.”

She smiled at me and asked what it was that had helped so much. (She knows of my life-long struggles with anxiety and depression.) I said, “Well, I’ve been sitting daily meditation for nearly 17 years now. Something should have shifted by now.”

The truth is, my daily practice of journaling followed by meditation have been the most powerful tools for restoring equilibrium and, therefore, deep happiness.

What’s something you know now about happiness that you didn’t know when you were 18 years old?
That being happy is a byproduct of living in alignment…where my inner belief systems match my outer actions. When I was 18, I tried to kill myself and spent three months in a hospital. If I knew then about living in alignment in this way, I don’t know that I would have felt the sadness I felt.

Have you ever managed to gain a challenging healthy habit—or to break an unhealthy habit? If so, how did you do it?
With a tremendous amount of forgiveness to myself. In my book, I tell the story of learning that we each have an infinite number of “do overs.” And that, when we fail in some way or another, we can simply begin again. In this way, I developed the capacity to repeat activities until they became healthy habits.

Would you describe yourself as an Upholder, a Questioner, a Rebel, or an Obliger?

Does anything tend to interfere with your ability to keep your healthy habits or your happiness? (e.g. travel, parties, email)
My children’s needs. Even though they’re all adults now, I will forever place them before me. (And I think that’s the right thing to do.) I can be totally focused on taking care of myself and doing the things that are best for me, like meditating or exercise. But, if my kids need me, I’ll put these things aside. Since being their dad is the greatest source of joy in my life, it’s kind of like trading one source of happiness for another. 

Have you ever been hit by a lightning bolt, where you made a major change very suddenly, as a consequence of reading a book, a conversation with a friend, a milestone birthday, a health scare, etc.?
All the time. I actually think of them more like asteroid strikes. While lightning strikes can be destructive, asteroids can knock you onto a different orbit. Though it’s just as unexpected; it changes your course. 

Has a book ever changed your life—if so, which one and why?
Too many to list here but I’ll try for three:

I read all three at one of the lowest periods of my life…from Pema, I learned that all things fall apart all the time and that suffering and sadness stem from trying to fight that.

From Sharon, I learned the deep blessing that comes from internal forgiveness, loving kindness to self, and the value of a faith beyond religion.

From Parker I learned the importance of living in alignment and being truthful with oneself. I also learned to have the courage to speak about my own struggles.

In your field, is there a common misperception or incorrect assumption that you’d like to correct?
That there’s a right way to coach people and, by extension, that there’s a right way to be. My long-time therapist liked to say that “There’s a right way. There’s a wrong way. And there’s the way that works.”

I wish more folks would focus on the ways that work.



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