Jerry Colonna | This Top CEO Coach Asks the Tough Questions that Leaders Aren’t Thinking About

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Jerry Colonna | This Top CEO Coach Asks the Tough Questions that Leaders Aren’t Thinking About

Jerry Colonna

Posted on December 10, 2019

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Jerry Colonna, the co-founder and CEO of, has achieved extraordinary success as a venture capitalist, executive, board member, and business coach for some of the world’s top CEOs and entrepreneurs. He was even called the “CEO Whisperer” by Gimlet Media! 

But the wisdom Jerry offers goes far past the boardroom and deep into philosophy, mindfulness, and what it really means to be human.

In this week’s episode of the donothing podcast, listen in as Jerry speaks openly about his impoverished beginnings, lifelong struggles with mental illness, and journey towards his own self-discovery.

Jerry also talks about his book, Reboot: Leadership and the Art of Growing Up, where he empowers leaders to thrive through deep self-inquiry, accepting failure, embracing compassion, and ultimately becoming a more human leader. 

In this episode of the donothing podcast, you’ll also learn:

  • How growing up in poverty still influences Jerry
  • When Jerry realized his relationship with money was unhealthy
  • Why motivations often lead back to love, safety or belonging
  • What the difference between Sabbatical and a vacation is
  • How long Jerry’s Sabbaticals last
  • What Jerry does on Sabbatical each year
  • Why Jerry has been journaling since he was 13-years-old
  • What Jerry writes about in his journals
  • How we process anxiety
  • What books have significantly influenced Jerry 
  • Why Jerry started meditating 17 years ago
  • What it means to find the right intention and the right awareness
  • Jerry’s ongoing battle with depression and suicidal thoughts
  • How meditation helps him get through depression
  • When Jerry became a “Nightstand Buddhist”
  • Why we must stop obsessing about always finding the answers
  • His thoughts about our constant fear of failure
  • How we can change our relationship with “success”
  • Why you should never hold your plans too tight
  • How to live a life with less judgement
  • Why Jerry moved from New York City to Colorado
  • How the move has improved his life
  • Why Jerry finds silent retreats “incredibly important”
  • What leaders will gain from a silent retreat

Connect with Jerry Colonna





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Buy Jerry’s Book, Reboot: Leadership and the Art of Growing Up

Reboot: Leadership and the Art of Growing Up

Jerry’s Favorite Books

Call it Sleep, by Henry Roth

When Things Fall Apart, by Pema Chödrön

Let Your Life Speak, by Parker Palmer

Faith: Trusting Your Own Deepest Experience, by Sharon Salzberg

Register Now for the Most Rewarding Leadership Challenge of your Life!

You’ve likely heard about the benefits of integrating mindfulness into your life and leadership. But where do you even begin? Or, how can you take your current mindfulness practice to the next level?

No matter where you are on your journey, the 2020 donothing Leadership Retreat was designed for you! Join me and other like-minded leaders as we get out of our comfort zones and focus on becoming the best leaders we can be.

Together, we’ll grow in ways never imagined through powerful teachings, mindfulness trainings, and undistracted time for real reflection and rejuvenation.

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Subscribe to the donothing podcast to discover simple, practical tips and tools from mindful, high-performing leaders that you can implement in your leadership philosophy today. 

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