Founder Jerry Colonna On How To Find Fulfillment In A Chaotic World

Welcome back to the Productivity Giants Series! We took a break, but now we’re back interviewing interesting and motivating people on all things productivity tips and workflow. Stay tuned to see who we feature this season!

Jerry Colonna has had a few exciting careers over the years – he started out as a venture capitalist, then worked as an independent coach, and now he’s an author and co-founder. 

His latest endeavor is a coaching company called, and was born out of his experience being one of the start-up world’s most in-demand executive coaches. Gimlet Media even hailed him as the “CEO Whisperer”! Reboot offers comprehensive leadership development for individuals, teams, and organizations, and operates on the belief that our work can lead to the full realization of our human potential. They promote the idea that “Work doesn’t have to destroy us. Work can be the way we achieve our fullest selves.”

Jerry’s book, Leadership and the Art of Growing Up, offers similar insight, and delves into why “radical self-inquiry is critical to professional success and healthy relationships in all realms of life.” In this book, he inspires the reader to hold themselves accountable for their choice and for the possibility of achieving their dreams. It’s a must-read if you’re looking for a chance to reset your goals and reconnect with yourself and with others on the path to success.

We talked to Jerry about setting healthy boundaries, the art of journaling, pivoting during the pandemic, and more. Check out the full interview below.

How has your business been impacted by the pandemic, and if so, what have you done to pivot?

We haven’t pivoted, but the single most important impact on the business has actually been how it’s impacted our clients. Many of our clients were terrified in February, March, April, and May. 

Things are a little bit better now, but it’s not just in the pandemic, it’s been the dumpster fire after dumpster fire after dumpster fire that’s been 2020. So, the shifts that have occurred in the business have occurred primarily in response to clients. To respond, we increased the level of support that we would provide them.

We have 10 individual coaches who work for Reboot, and every one of them went into overdrive providing support to their clients. I myself ended up working pretty much seven days a week for weeks on end. It’s been an honor to be able to be there for all of our clients in that way during a particularly difficult time. So, I wouldn’t say we pivoted, I would say we doubled down on what it is that we do.

What would be your best advice on setting boundaries between like work and home life for someone adjusting to remote work?

Let’s specify what boundaries you’re talking about – there are a couple of different phenomena that you’re touching upon. One is the fact that in response to this, what we’ve seen isn’t in response to the reordering of the norm right now, whether it’s pandemic or economic or a combination of both. What we’re seeing is what one of my colleagues refers to as the “blursday.” The “blursday” effect is every day just blurs into another and it’s all the same, and you wake up and you stumble into your computer and you’re just at your computer until you’re not. That’s one phenomenon.

Another phenomenon is “I’m trying to squeeze in everything that’s going on in my life”. For example, in between the Zoom call I’ve got a diaper that I have to change, or I have a school-aged kid that can’t access their classroom, or I’ve got a doctor’s appointment next week, and I don’t even know how to begin to plan for that. So there’s that phenomenon.

And then you have this sort of collegial phenomenon going on, which is, I know that you’re struggling because you have school age kids, I’m a single person, or my kids are out of the house. So therefore, I take on extra work because I feel bad for you, thus obliterating whatever work life boundaries that normally would exist for me. 

“Make sure that you’re setting up support systems so that people have the space to understand that it’s okay to actually turn off your devices at some point.”

All of those things are operating simultaneously for most of the client companies that we work with. So, what I would say is in response is, it’s incumbent upon those who have the most power within the organization to set the stage properly. They need to explain to people the importance of actually backing away from the computer and the importance of a reordered expectation around productivity.

Many times what’s happening is an internalized sense of responsibility as it relates to productivity that is driving a lot of this anxiety, but it’s not the only thing. The other thing that’s going on is that people are turning to work because it’s the only area of their lives where they feel in control. 

So people are doubling down and spending more time on answering emails or whatever it is that defines work for you, because being out in the world is scary right now. The best advice I would say is to make sure that you’re setting up support systems so that people have the space to understand that it’s okay to actually turn off your devices at some point. If possible, if you have a yard, go out in the backyard and toss a ball around with one of your kids.

You’re an avid journaler. Can you shed some light into your process for journaling?

I’ve been journaling every day since I was 13, and now I’m 57, so I’ve been doing it a long time. I usually start off with some sort of statement about how I’m feeling and it might be, “Right now, I feel really calm.” A lot of times it’s a review of the day before, or it might be about something I feel particularly anxious about or things that I may feel angry or scared about.  But a lot of times it’s just observations that I make about my life.

My journaling is really an extension of my mindfulness practice. So when people say, “Well, how long do you meditate for?” I say, “No, I meditate for 15 minutes, maybe 20 minutes, maybe 30 minutes.” But the truth is even that journaling is a kind of premeditation, because it’s sort of like you’re kind of doing the body scan, right? “How’s my breath, how’s my posture?” And you’re just sort of taking stock of yourself. The practice of journaling is kind of taking stock of my emotional wellbeing and it sets me up for a more supportive meditation session.

What bad advice do you hear often?

I’m not a big fan of life hacking. I am a fan of being gentle on oneself and focusing on incremental progress. There’s often an infatuation with a panacea approach. You know, if we all just put Irish butter and MCT oil in our coffee, then we’d all be fine. It’s like, no, life doesn’t work that way.

The answer to that bad advice question is really a bucket of things all falling under the rubric of the expectation that one-size-fits-all answers are the answer. It takes more work – it takes knowing oneself, removing the obstacles in one’s life that are the true obstacles that are holding themselves back.

“If I’m not willing to answer hard questions, I’m really not going to transform, I’m just going to change things on the edges. That’s not transformation, that’s just changing.”

A lot of people will ask me about transformation. The truth is that transformation requires two things. The first is the willingness to honestly fiercely confront your own self. In my book I referred to as radical self inquiry. One of the core defining questions is, “How have I been complicit in creating the conditions that I say I don’t want?” So for example, “How have I been complicit in creating a life where I feel constantly overwhelmed and busy and behind?” And equally important, “How has that feeling served me?” Because if I’m not willing to answer those questions, I’m really not going to transform, I’m just going to change things on the edges. That’s not transformation, that’s just changing.

The second part of transforming is patience. And people like James Clear have made it very clear, no pun intended, that, changing habits takes repetition and time, and a kind of patience that requires us not beating ourselves up. 

What book has changed your life and why?

There are three books that I often cite as not merely changing my life, but saving my life. The first is a book called When Things Fall Apart by Pema Chodron. The basic premise of that book is that things are falling apart all the time, and we suffer because we don’t recognize that and because we wish that it wasn’t so. That book was especially helpful when the stress of the pandemic’s economic and health influence started to take hold for me.

The second book that saved my life was a book called, Let Your Life Speak by Parker Palmer. Parker explores the necessity for what we refer to as an inner and outer alignment where what I do on the outside must match who I am on the inside. And the relationship between that misalignment and depression and anxiety and bad behavior in one form acting out in another form. And that’s really powerful.

And the third book is Faith by Sharon Salzberg, the Buddhist teacher. Sharon fiercely and bravely explores the traumas of her own childhood. And what that showed me was that doing so in a public way was not only acceptable but helpful to other people. And, uh, I will forever be grateful to her for that.

Final question, what’s the most worthwhile investment that you’ve made?

Nothing has been as important as the work I’ve put into being the best possible father I can be. That doesn’t mean that I’ve always been the best father I can be, but nothing has been more important and more rewarding than the energy I put into my relationship with my children who are all adults now. That investment dwarfs the ROI of anything else I’ve ever done in my life by far.

Check out Jerry’s book here:

Reboot: Leadership and the Art of Growing Up

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