Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year (#554)

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“What benefit do I get from the conditions I say I don’t want?”

— Jerry Colonna

Jerry Colonna (@jerrycolonna) is the CEO and co-founder of, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. For nearly 20 years, he has used the knowledge gained as an investor, an executive, and a board member for more than 100 organizations to help entrepreneurs and others lead with humanity, resilience, and equanimity.

Prior to his career as a coach, he was a partner with JPMorgan Partners (JPMP), the private equity arm of JPMorgan Chase. Previously, he led New York City-based Flatiron Partners, which he founded in 1996 with partner Fred Wilson. Flatiron became one of the nation’s most successful early-stage investment programs. Jerry’s first leadership position, at age 25, was editor-in-chief of InformationWeek magazine. He is the author of Reboot: Leadership and the Art of Growing Up.

Jerry lives in Boulder, Colorado. This is his second appearance on the podcast. His first can be found at

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Musicor on your favorite podcast platform. You can watch the interview on YouTube here.

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#554: Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear the last time Jerry was on the show? Listen to our first conversation, in which we discuss being complicit in creating the conditions in life we don’t really want, nagging self-doubt, finding time for self-discovery, confronting the difficulty most of us have with saying “no,” acknowledging compassion from a distance, journaling, guilt versus remorse, and much more.

#373: Jerry Colonna — The Coach with the Spider Tattoo
  • Connect with Jerry Colonna: | Twitter


  • When there’s not an unchecked global pandemic going on, Jerry has been taking an annual two-month sabbatical for the past 10 years. He tells us about the first one that kicked off this tradition, how it came about, and the inner thoughts that initially tried to talk him out of it. [07:35]
  • A counter to the “Can I afford it?” question someone of any means might ask themself when considering the form their own sabbatical could take. [14:25]
  • What makes a sabbatical work in preparation and practice? [19:34]
  • What kind of rookie sabbatical mistakes did Jerry make early on, and what did they teach him? [23:47]
  • How does Jerry handle email on a sabbatical? [25:56]
  • What happens if there’s a crisis that requires Jerry’s attention when he’s on sabbatical — and how would someone communicate this to him [27:38]
  • Thinking back on past sabbaticals, what factors contribute to emerging fully charged versus least recharged? [29:33]
  • Shooting stars, terrible first drafts, and sabbatical-related epiphanies about productivity. [33:37]
  • How might we reframe and reduce the complexities that keep us from carving out time for sabbaticals so we don’t suffer consequences for neglecting them? [38:44]
  • Explorations of complex structures, DNA versus subroutines, and hot and cold boredom. [45:46]
  • Advice Jerry would have for someone considering a sabbatical who is unsure how to begin untangling themselves from the complexities that keep them busy. [53:58]
  • Thoughts on feelings of loneliness or alienation that a sabbatical might conjure up, and how changing the surroundings and/or company you keep can make all the difference. [57:39]
  • Resources Jerry might suggest to listeners who are considering the possibility of a sabbatical. [1:11:51]
  • Lost by David Wagner. [1:16:44]
  • Parting thoughts. [1:19:57]


“What benefit do I get from the conditions I say I don’t want?”
— Jerry Colonna

“I was at my most productive when I stopped trying to be productive.”
— Jerry Colonna

“Sabbatical is a time of thinking differently, of considering things differently.”
— Jerry Colonna

“For many of our friends who are in the startup land, the thought of taking a weekend off is as terrifying as my thought of taking two months off. And that’s a problem. That’s a problem that not only affects them physically, it’s a problem that affects them mentally. It’s a problem that actually, I would argue, undermines their leadership capabilities and creates toxic environments.”
— Jerry Colonna

“By law, you have to build into the structure of the business sick time, vacation time, parental leave, all sorts of policies. And then periodically something awful happens, and we say, ‘Okay. Let’s build in some mental health time.’ But it’s always after some sort of horrible event.”
— Jerry Colonna

“A lesson I learned was to not turn the sabbatical into another source of self-criticism.”
— Jerry Colonna

“The number one rule in sabbatical is Sabbath. Rest. Rest. The body needs rest; the mind and heart need rest. That’s the simplest way I can put it for you.”
— Jerry Colonna


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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6 Replies to “Jerry Colonna — How to Reboot Yourself and Feel Unrushed in the New Year (#554)”

  1. Thank you. Brilliant topic and guest. This is a lifestyle that should be far more commonplace than reality. There has never been a better time to implement such advice.

  2. Deeply grateful to the emptiness that invites in the grace of serendipity that was finding this podcast in my feed. Thank you Tim and Jerry for a perfectly timed conversation for me to push forward into my Wisdom Sabbatical!

  3. Profoundly striking to hear these two enlightened souls each talk about being seriously suicidal. Both are shining examples of resiliency and post-traumatic growth; they learned to fuel a life of serving and meaning from the depths of despair. I applaud their honesty, authenticity and vulnerability.

  4. This was a much needed podcast for me, having just returned to work after a 15 month Sabbatical, and having listened to it (and loving the idea of taking two months off/year) it has reminded me how much I benefitted from my time off. For me, what nearly prevented me from taking a Sabbatical were feelings of guilt. My own personal coach helped me work through “guilt” feelings before I was able to give myself permission to take this time off-you see-I had been working for 20 years as a psychotherapist, and had just finished breast cancer treatment (& had worked through my treatment). By the end, I was exhausted & it was clear that the two weeks that I afforded myself at the end of my radiotherapy was not enough. So, through my own coaching sessions I was able to grant myself permission (something that didn’t come naturally given the work ethic that was passed down to me by of one of my parents).

    One of the things that resonated with me most, was when Jerry discussed the idea of not trying to achieve anything while on Sabbatical-which was exactly what I did initially. “I’m going to Greece to write a book”. I must have felt deep down that I needed to justify this time off-by saying that I was going to write a book-something that I have wanted to do for a long time, but realised it wasn’t going to happen in Greece! Instead, I took long walks up hills (not a soul in sight because this was all during a tight lockdown), I learned to cook grilled octopus (and have mastered this dish if I do say so myself)…this Sabbatical was exactly what my soul needed.

    Tim-you asked Jerry for resources on Sabbaticals, etc. The book that my own coach recommended to me is called Working Identity by Herminia Ibarra-a must read for anybody considering changing careers or who is just re-evaluating what they want to do with their lives (often a precursor of a Sabbatical).

    I can also recommend the book “Time Off” by John Fitch & Max Frenzel. They discuss the importance of having a rest ethic as well as a work ethic. Again, another must-read.

    Tim-I related so much to the feeling of exhaustion that you described after a day out hiking/climbing with your male friends and what struck me (I’m coming at this from a psychotherapist’s perspective) is that the reason you absolutely love that feeling (contrasting it with sitting in Starbucks during work hours with a bunch of people you have not a whole lot in common with) is because when we are so physically exhausted, it is difficult for our minds to race; it is difficult for us to worry or experience anxiety when we are in such an exhausted physical state, because the two responses are incompatible (physical exhaustion/calmness & worry). Perhaps that is the function (for you) of being so physically exhausted-the unintended consequence is that it slows down your mind/helps you relax?

    I may have got this concept all wrong, but the “cold boredom” that Jerry described sounds very similar to what we (in psychotherapy) describe as “contentment”. “We are just stirring the oatmeal”-and not worrying about or thinking about anything else. It’s not necessarily “happiness”-but “contentment”-the two states are different:).

    All this to say-I loved this episode and I do believe that we, as a society need to be talking more openly and honestly about the benefits of taking extended periods of time off work.

    Thank you, to both of you for getting the conversation going!

  5. Hi, Tim and Jerry, as someone who has taken 2 sabbaticals of 6-8 months during her career, I really appreciated your podcast, and the encouraging message it gives listeners. As an Integrative Medicine physician, I certainly see how what I call “The Addiction to Doing” influences our physical and mental health, which is why I have written about it on my blog and a local magazine column. I think Tim’s comments about the odd feeling of hanging out among people he perceived as “marginal” because they did not appear to be working during the day has direct links to “withdrawal from the addiction to doing.” Here is the substance of my thoughts on this VERY pervasive addiction, and how it impacts our health. Thanks again for your encouragement for addressing it. (We doctors are VERY addicted!!)–Joanne (“JP”) Pizzino, MD, MPH, FACOEM

    The Addiction to Doing
    Are you a human being or a human doing? Looking over my life, it is pretty clear that I am a human doing. Many of us highly productive over-achievers are. A few generations ago, it may have been thought that doing was a gender issue, with men being more “doers” and women more “feelers”. Now, however, those distinctions are too limiting. In fact, as you look at the pace of modern human life, it could be argued that nearly all of us have become human doings. Working at that which gives us meaning or, at least, a paycheck. Grooming the shelters and vehicles we dwell in: bodies, cars, homes. Climbing the corporate ladder, or making sure our kids can, with piano lessons, soccer, summer camp. Running around in circles. Jumping to conclusions. Dodging the bullet. We are nearly always doing something. In fact, so much so, that we often can’t even stop to allow our bodies to do those effortless “no-things”, such as sleep and elimination. We even have to “do” meditation in order to get ourselves to “do no thing.” The word undoing also implies doing: breaking addictions, losing weight, relaxing.

    It was recently expressed to me that one of the worst parts of being ill is that “you can’t get stuff done.” True, there are many consequences for being unable to fulfill our responsibilities. So, we often reach for the bandaid medication or surgery rather than getting to the root cause, just trying to get stuff done.. However, it is also the withdrawal from the addiction to doing which is so uncomfortable. What are the symptoms of this withdrawal? Guilt, shame, blame of myself and others. Of course, there is also a great temptation to point the finger outside myself and focus on all the “forces” which require me to do: rent, taxes, body maintenance, childcare, creative expression needed to nurture whole-personhood. But what really is at the source of the need to DO? If we peel back the layers of this essential root cause question, we see that we come up with some version of lack of worthiness.

    You will never be enough.
    You are so inadequate.
    You are useless.
    You are worthless.

    The concept “I don’t matter” is at the heart of the addiction to doing. Between the horror of feeling insignificant to anyone else and the anguish of deeming myself “nothing”, I can do. I literally do until I drop. Doing takes that agony and hides it, soothes it, distracts from it. Psychiatrist Lance Dodes, MD, takes a radical stance on addiction in his book The Heart of Addiction. Rather than labeling it as a disease with a twelve-step “treatment”, he describes it as a reaction to being in an intolerable situation of feeling out of control. The internal rage at this helplessness causes us to do something. Reach for alcohol, drugs, food, work, exercise, gambling, sex. Something. Something is better than nothing.

    We all detest the helplessness of feeling out of control. As a founding member of Control-Freaks-R-Us, I really can’t think of anything worse. Being in the straightjacket of “do nothing”, I reach for my “fix” of doing something. Even when my somethings fail or mess up, at least then I can feel: disappointment, anger, frustration, annoyance. Doing is also at the center of mood disorders, such as depression and anxiety. In depression, the feeling of helplessness or hopelessness to change our circumstances overwhelms us. In anxiety, the constant inner directive to “do something” to avoid a perceived threat engulfs us.

    Self Empowered Healing is a process which helps us identify and take charge of the doingness, rather than being victimized by the addiction. Rather than one more thing on the “I-Don’t-Want TO DO List”, Self Empowered Healing gives us laser-like precision on what is directly relevant to physical, mental and spiritual health. It gives us control over the things we actually can control. Being in control is the ultimate doing. That’s why we addictively reach for something to do when feeling out of control. And yet, despite our many illusions to the contrary, there is very little we can actually control. As one of my patients told me, there are only three things we control:
    1.) What we put into our bodies, ie. food, drink, medications, recreational drugs, nutraceuticals, etc.
    2.) What we do with our bodies, ie. how we move, exercise, sex, the personal environment we chose to live in, etc.
    3.) What we do with our minds, ie. which feelings and thoughts we chose to entertain.

    That’s about it. A dauntingly small plate. Not my family, my co-workers, politics, gasoline prices, or pandemics. Self Empowered Healing actually gives us back a feeling of control by placing that which we can control directly within our grasp. With expert guidance on Functional Medicine approaches to healing, precisely focused mind-body practices to enhance outcomes, and compassionate mentoring to overcome stumbling blocks, you can get past the helplessness and hopelessness of disempowering health conditions to have the well-being for the life you were truly born to live. Instead of reaching for a quick fix medication or surgery so you can get back to your addiction to doing, empower yourself to vitality and wellness with Self Empowered Healing.

    Joanne Pizzino, MD, MPH, is board-certified in Preventive Medicine and diplomate-certified in Integrative Medicine. After her own self-empowered healing epiphany in 1997, she has guided people to live healthier through both Eastern and Western medicine, ancient and ultra-high-tech healing.

  6. Amazing podcast on this topic. Many people make their New Year resolution but they failed. The reason they failed is they don’t use correct techniques to reboot themselves.