Jerry Colonna — The Coach With the Spider Tattoo (#373)

“You are not alone. And just because you feel like shit doesn’t mean you are shit.”
— Jerry Colonna

Jerry Colonna (@jerrycolonna) is the CEO and cofounder of, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders.

Prior to his career as a coach, he was a partner with J.P. Morgan Partners (JPMP), the private equity arm of J.P. Morgan Chase. Prior to that, he cofounded New York City-based Flatiron Partners with Fred Wilson, which became one of the nation’s most successful early-stage investment programs. His first leadership position, at age 25, was Editor-In-Chief of InformationWeek magazine, and now he has returned to the written word with his first book, Reboot: Leadership and the Art of Growing Up.

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#373: Jerry Colonna — The Coach With the Spider Tattoo


Want to hear an episode with someone else who understands the value of coaching? — Listen to my conversation with Eric Schmidt, in which we discuss the immeasurable impact late coach Bill Campbell had on Silicon Valley’s rise as a veritable modern superpower. (Stream below or right-click here to download.)

#367: Eric Schmidt — Lessons from a Trillion-Dollar Coach


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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…


  • Connect with Jerry: | Twitter


  • What’s the story behind Jerry’s spider tattoo? [05:10]
  • What happened at an Olympic bid meeting in 2002 that would change Jerry’s life? [11:39]
  • Jerry talks candidly about a suicide attempt at age 18 and spending three months in a psychiatric hospital. [18:17]
  • What’s the difference between responsible and complicit and, in 2002, how was Jerry complicit in creating the conditions in his life that he would have said he didn’t want? [19:30]
  • Three important questions Jerry’s therapist taught him. [23:02]
  • An example of something Jerry needed to say during this period of time that he didn’t say or that wasn’t heard. [24:24]
  • What did Jerry do to overcome the nagging self-doubt and unanswerable questions that were crushing him at this point? [26:12]
  • How did Jerry find his way to coaching, and what three books guided him in that direction? [28:42]
  • If he were to hazard a guess, how much of Jerry’s call to coaching was finding relief in taking the focus outside of himself and, in a way, healing his younger self? [35:12]
  • How does Jerry get through to fellow high-achievers who don’t think they have the time, patience, or need for self-discovery? [38:30]
  • The first question Jerry asks: “How are you really feeling?” [39:41]
  • How does Jerry work with the chronically busy? [43:11]
  • Jerry takes a look at how I’ve historically dealt with busyness and breaks it down — along with saying “No” and when (and why) this is most difficult for me. [45:54]
  • There are three basic risks that we’re all trying to manage all the time: love, safety, and belonging. [59:35]
  • Tools, books, and approaches Jerry has found helpful for people who have difficulty saying “No” or establishing boundaries. [01:01:43]
  • “All beings own their own karma. Their happiness or unhappiness depend upon their actions, not my wishes for them.” [01:03:50]
  • A boundary tool that acknowledges compassion — but from a distance. [01:05:21]
  • To Jerry, the challenge isn’t in not having a tool for maximizing the efficiency with which we overcome our struggles. The challenge is in the meaning that gets put into a situation before a tool can even be applied. [01:06:35]
  • Like the Jerry of Seinfeld fame, we all have a Newman (or several) vexing our lives in some way. How might we humanely confront, converse with, or even sever ties with these unhealthy relationships? [01:07:21]
  • How does Jerry get someone from the point of intellectually agreeing with what he’s saying to actually putting it into practice and changing their behavior? [01:12:38]
  • As a 55-year-old who’s been journaling daily since he was 13, how does Jerry prescribe the practice as a way to drive personal results? [01:15:16]
  • Guilt vs. remorse. [01:17:30]
  • Marie Ponsot, the crow, and the importance of letting the crow speak in the journal. [01:18:14]
  • Jerry describes his typical bedtimes and mornings, when he fits in time for journaling, and what his journaling prompts and processes look like. [01:22:31]
  • How journaling can help us accept the totality of what’s going on in our lives by allowing our different voices to speak — the “multitudes” we contain per Walt Whitman’s Song of Myself. [01:26:13]
  • On Radical Acceptance by Tara Brach [01:28:19]
  • How Jerry has used Marvel’s Hulk and Thor to reconcile the different parts of himself and understand that they each serve a purpose — recalling Carl Jung’s notion of The Shadow. [01:29:20]
  • Jerry walks us through the time he made a difficult decision to say “No” — and focused on something narrowly — that ended up being life-changing in retrospect. [01:34:29]
  • Jerry’s advice to anyone who finds themselves in a similar position — or his younger self at this junction. [01:41:58]
  • How journaling, meditating, and answering certain questions has helped Jerry cope with rage-fueled anxiety and tame his inner Hulk. [01:44:01]
  • Where an aspiring beginner can learn more about loving kindness, aka metta meditation, and what it’s helped me discover about myself. [01:47:48]
  • What new behavior or belief has greatly improved Jerry’s quality of life? [01:50:16]
  • What would Jerry’s billboard say? [01:52:19]
  • Closing thoughts. [01:55:02]