Finding Yourself in Unaccustomed Earth

Human nature will not flourish, any more than a potato, if it be planted and replanted, for too long a series of generations, in the same worn-out soil. My children have had other birthplaces, and, so far as their fortunes may be within my control, shall strike their roots into unaccustomed earth.

― Nathaniel Hawthorne

I often dream of the past. Sometimes–rarely–such dreams are challenging, awakening memories I’d rather lay dormant. More often, though, these dreams are pleasant; a sort of re-visitation that allows me to see things in a new light.

In those dreams, I often return to old places of work. The Community Bookstore in Park Slope, for example, where for more than a year I spent my weekends, earning money to supplement the scraps I earned as a reporter, or the magazine where I worked earning those scraps.

I remember one dream in particular where I visited the reporters’ bullpen of that magazine. I floated, wraith-like, in and through the stark white sheetrock walls and above the red-orange carpet, watching folks who turned out to be important mentors, elders churn out yet another edition.

I’ll usually wake with a mix of reverie, nostalgia, bittersweet knowledge of my inability to return to the past, and, even more, the sense that if only I knew then what I know now, then that experience would have been better.

I suppose such is the nature of the remembrance of things past. We return again and again to the places that marked us, the moments when we turned, grew, took steps towards becoming who we are now.

Nearly thirty years after first walking into that magazine’s offices as a summer intern, I’ll never shake the sense that that moment created the rest of my life.

I think such is the purpose of these dreams. I’ve had enough of them to know they come in moments of transition; reminders from the unconscious of where you’ve come from, the futility of wishing to go home again, and the sense of what is to come.

What is to come, of course, is the rest of our lives. For me, these stages have come in ten-year increments. I spent ten years growing up in Flatbush and then moved to another part of Brooklyn. I spent ten years struggling to become a man, including a powerful and lasting bout of depression, and then emerged an intern at a technology magazine–far from what I thought my future would be, far from the poet and writing teacher.

Ten years in publishing. Just over ten in venture capital. And then again, nearly ten as a solo entrepreneur, a coach.

Each phase–each almost-decade–drew me closer in, closer to my truest self. Each transplantation into unaccustomed earth brought me closer and closer to finding my self.

By now the process is familiar: tremendously fearful excitement molded by the sensation of utter incompetence. It’s like my roots, finally free of the confines of that old pot, don’t know what to make of the new space, fresh nutrients, and abundant air of unaccustomed earth.

There are two ways to see the notion of finding one self in new soil. There’s the view that it’s a surprise–“Look Ma, I’m in a new place!” And then there’s the deeper more lasting view where we use all that additional space, nutrients, and air to discover more about ourselves.

I’m in this place again. I’m once again finding myself in unaccustomed earth. Merging my practice with that of my dear friend and collaborator, Khalid Halim and opening myself to the gifts of Ali Schultz and Dan Putt, my little business has been re-potted.

The new pot is Reboot is first and foremost a coaching company. Khalid and I will maintain our individual and group coaching practices. But by combining our efforts, we hope to make our collaborations seamless and more effective.

More to the point, though, by combining those efforts, I hope to live into the possibilities I’ve been nurturing for years now: to increase the impact of the work by reaching more people.

For it’s really about the work. It’s about making the work more accessible with the launch of a podcast where we can speak with people who might not otherwise be able to be coached. Or by the increase in the frequency and effectiveness of one- and multi-day workshops, discussions, and what we refer to as boot camps. And through the development of tools and services that ultimately allow each of our would-be clients to help themselves and each other.

As I often say, there aren’t enough elders, mentors, therapists and coaches in the world to meet the collective need. We have to help ourselves. In the end, this is really what Reboot is all about it.

It’s not Jerry 3.0. And it’s more than a “coaching company.” It’s a platform where we’ll use the existential challenges that arise from our work lives to move more fully into our adult human selves and, thereby, somewhat and some times ease the pain of the vagaries of every day life.

My choice of inclusive pronouns is purposeful. Our intent, this happy band of open-hearted warriors I’ve collected around me, is to abide by what we teach our clients: to create the company that we want to work for.

We come together not for conventional notions of success but to attempt, as David Whyte says in Crossing the Unknown Sea, “Good work, done well for the right reasons.”

Of the things that move me about Reboot, this excites me the most. The company I want to work for has values built around transparency and authenticity, around owning our own shadows and cutting the monsters in our heads down to size. It means good work, done well for the right reasons. It means “full-catastrophe living” as John Kabat-Zinn calls it–that is, mindfully living with the ups and downs of life. It means our full selves showing up at the office. It means, each of us holding the responsibility for creating an environment in which we not only have fun but experiment and try different things. It means holding each other accountable for creating a company whose work, values, and view of itself is dedicated to the proposition that implicit in work is the possibility of the full realization of human potential. Work does not have to destroy us. Work can be the way in which we achieve our fullest self.

If we can embody those values, we’ll show our clients how to do the same. To strive for anything less would be inauthentic.

I often speak of my dedication to the proposition that work should be non-violent to the self, non-violent to the community, and non-violent to the planet. I didn’t want to create Reboot to merely teach that. I wanted to create something that lives that. And, in doing so, live the teachings.

I owe it to my teachers, to the elders and mentors, the allies who have entered, re-entered, or exited my life to live this out. I owe it to my children to test more fully that proposition for I want them to come into their adult lives knowing this is possible.

It would be incomplete and, therefore, inauthentic for me to speak of this transition without acknowledging and honoring the other transitions in my life. This new ten-year cycle I’m entering isn’t merely marked by the launch of Reboot. For my family–each of us individually and the collective whole–is also going through a transition.

As I write this post, for example, my oldest son works on a career for himself that honors and celebrates his kinesthetic being; my daughter teaches kindergarten kids in a struggling part of Nashville; my youngest polishes his college application essays; and Barbara, their mom and my friend of 32 years, launches her third nonprofit as she navigates her own new life.

Each of us is finding ourselves in unaccustomed earth.

I pause, noticing the resurgence of those dream-like feelings: the mix of reverie, nostalgia, and the bittersweet knowledge of our inability to return to the past. And with that, I savor again the fearful excitement.

As I write of the exquisite mix of uncertainty about the future and its possibility John Luther Adams’ In the White Silence, comforts me, urges me on.  I turn 51 this December and, for the first time in my life, I’m beginning to feel like an adult. In acknowledging that, I’m struck by the notion that perhaps my dreams, too, are ready to shift. Honoring and holding onto the past, remembering and never forgetting who I was, I think I’m ready to dream of the future.

Welcome, Jerry, to

  • Barbara Pantuso

    This post is beautifully written – thank you. As one who intentionally and regularly plants herself in unaccustomed earth, I always love when I dream of the past. It reminds me that while we can’t return to the past, we do carry it with us more deeply than we realize. The memories season us and remembering them somehow makes me feel more rooted during transitions. I wish you all the best with your transition…or rather, your reboot.

    • jerrycolonna

      Thanks, Barbara, for the kind words. I never thought of myself as intentionally re-potting myself but, after reading your note, I think I may be similar. I know that Hawthorne quote has always spoken to me.
      Thanks for the good wishes.

  • fredwilson

    Great long wandering post Jerry. It covers so much fruitful territory. I’ve been there to see the last two decades and I have to say you have emerged from them happy, healthy, and oozing calm. You are a testament to the work you urge us all to do on our selves.

    And congrats on the launch of Reboot. It sounds great. A coaching collective as it were. Anything you and your colleagues can do to increase the accessiblity of your teachings and your group sessions, the better off we will all be

    Mazel Tov

    • jerrycolonna

      Ah my friend. I’ll treasure this response. Thank you. Thanks too for being there to witness my meanderings. I’ll admit I remain terrified of having colleagues and being responsible to others. But then again, so do my clients so what the hell.
      BTW, I almost mentioned the numerous dreams I have of our working together again but I thought that would be too weird. 😉

    • Khalid Halim

      Fred- It was a blog post of yours years ago that lead me to cold email Jerry. At the time I didn’t realize how many of those cold emails he got a week. For some reason he responded and one of the most significant friendships of my life was created. I just want to say thank you to you and to let you know how you contributed to all of this.

      • fredwilson

        Wow. That’s great to know. I had no idea!

        • jerrycolonna

          Crazy, eh, how we unknowingly impact the world.

          • fredwilson


  • Elizabeth Kraus

    I am speaking at Denver Startup Week this morning and one of the questions I am prepping to answer is “Why are so few women in startups?”. I started thinking about what hurdles I had to get over to be an entrepreneur and I think this was it: The only entrepreneurs I knew as a child were people who had completely neglected their families, personal health and in many cases their values to make money. I didn’t want to be one of those people and I thought I had to be one of those people to be successful. It wasn’t until I met successful entrepreneurs who’s businesses were making a difference and who nurtured their personal and family life, as well as their business, that I wanted to be an entrepreneur. I have a hypothesis that the single most important thing we can do to bring more smart women (and men – millennial men especially) into the startup community, is to showcase people who are successful not despite the fact that they have a meaningful business and full-life, but because of it. I hope Reboot will do this and I look forward to watching. Thank you.

    • jerrycolonna

      I think you’re onto something important Elizabeth. That notion, that you have to disappear into the fire (as I refer to it), is not only false, but leads to a violence that not only affects women but men as well. And perhaps worst of all, our kids.

  • daveschappell

    I love this post. I really identified with the opening quote, and can deeply relate with the transitions you describe. I feel like I’ve had my own major transitions over the years (accountant, tech/product manager, entrepreneur/founder), and have spent the last few years since selling TeachStreet thinking about what my next transition will be — or, even more honest, wondering when I’ll find that next spark of excitement, and have the courage to pursue it. I’m off to explore Reboot — congratulations, Jerry!

    • jerrycolonna

      Thanks Dave. Thanks too for your honesty.

  • panterosa,

    This is an interesting piece. An exciting transition for you. I hope it bears the fruit you wish it to. How do Buddhists bless things?

    In here though I sense some friction between being in one’s comfort zone, for it’s comfort and ability to work on mastery, and the need to push that boundary and get out of the comfort zone to grow. For many, the comfort/expansion is a long cycle. Is part of Reboot defining these cycles and lengths?

    As you know (too well), I’ve jumped fields and made myself an outsider as often as possible. Sometimes this looks to you (and my mother) as a lack of focus, of the notorious “squirrel effect” of distraction by shiny and new. I will counter though (not as a defense per se, but to reveal my internal logic) that it’s been constant change that has kept me in what I equate with the continual exponential growth, and to build comfort with change itself. To always run up changing inclines makes for a better runner no?

    I found out recently at an industry shin dig, to which I am a newcomer and outsider, that the work I have done with my cofounder in a few years is the work of at least 10-12 industry people (who actually get paid!!). We expected that to gain recognition by them to need to exceed their bar, and in essence we redefined it to the highest degree.

    That, plus the deep commitment to ‘being the kind of place where I’d like to work’ has attracted our first non-solicited applicant, wanting to, as you say, take the lessons from the last phase and grow in a younger company, launching new and the challenges of that excitement. A very rewarding moment.

    • jerrycolonna

      We say, “Bless this thing.” :)
      I don’t see that as an assignment for Reboot but I wouldn’t be surprised to see it come up in the work.

  • Pete Bruce

    Congrats on Reboot and thank you in advance for all the people you and your company are sure to help.

    Another great post. Being 27, the fact that you are just now feeling like an adult at 51 makes me both terrified and hopeful. I hope I reach adulthood sooner but wouldn’t mind the wait if it means I will have the kindness, perspective and calm your life embodies.

    “we scheme about the future as we dream about the past, when just a simple reaching out might build a bridge that lasts”-John Hiatt

    Thank you for building that bridge.

    • jerrycolonna

      Thanks Pete. I was such a baby at 27.
      Glad to see that I’ve fooled you and made you think my life is calm.

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  • William Mougayar


    I like how you mix introspection, reflection and forward thinking to end-up with an energized state of mind and readiness for what’s ahead.

    Best of luck and much success ahead with the new Reboot.

  • Mary Colonna

    As your big sister I like to take credit for being one of your earliest mentors – that I had a little something to do with who you have become. I’m happy to say I look back at my past work with no regrets and a great deal of satisfaction. May your energy impel you to reach even further than you have already done. The fifties are a great decade! Not so sure about the sixties, but I’ll take your enthusiasm as encouragement. May Reboot prosper.

    • jerrycolonna

      Thanks Mary. You were definitely a mentor (as well as an elder..;) )

  • Wade

    Late to the party but so damn happy to be here. I felt a strange wave of relief when I saw this. Looking forward to following and hearing more from the team.

    • jerrycolonna

      What a curious response, Wade. Why relief?

      • Wade

        Well, it means I’ll be reading more from you – and that’s reason enough to celebrate. @bijan:disqus Sabet’s repost of “Up and to the Right” introduced me to The Monster in Your Head, and it’s become the blog I look forward to reading most.

        — Thinking on it more, I suppose the relief is a feeling that there is more head-clearing coming down the pipe. I read a lot of great blogs for the Mattermark Daily and get to consider the ideas of people I truly admire – but the posts usually center around Bitcoin, or mobile, or net neutrality. All very important subjects, without a doubt, but my head rarely feels clearer after reading them. Afterwards, my brain is buzzing – they’re exciting, but they usually don’t lead to prolonged reflection. Your blog offers a window into the shared human nature behind these big ideas.

        It’s inspiring. For a guy who never comments, I’m long overdue to say thank you for writing. Thank you. I really appreciate your posts.

        • Wade
          • jerrycolonna

            Bijan is a gem of a human.

        • jerrycolonna

          I’m smiling deeply and mentally bowing to you. Thanks for commenting. It shows that you’re leaning into being vulnerable. I’ll admit a little fear popped into my head in reading your note as the truth is, I don’t write nearly as much as I’d like. Consider though, subscribing to my podcasts at You may also enjoy those.

          • John

            I’d like to agree with you that you don’t write as much as we’d like either 😉 That’s what has me so excited about the podcasts. Thanks for continuing to spread your wisdom and perspective. It’s appreciated.

  • Peter Maffey

    “As I often say, there aren’t enough elders, mentors, therapists and coaches in the world to meet the collective need. We have to help ourselves. In the end, this is really what Reboot is all about it.”

    First of all, congrats on sending those roots of yours into new depths with Reboot.

    I have noticed as a son of the baby boomer generation, that you (collectively) discarded your elders, your mentors, teachers, etc. to purposefully break away from a warped system. The result has been a world of rapid change, but also, a generation that now should embody the role of elder and mentor, instead, is frightened of aging, preoccupied still with the travails of youth, and largely, alone.

    As a growing man becoming still an adult, it is utterly refreshing for me to hear you, Jerry, embrace the role of elder… to speak of the cycles of life with acceptance alongside the struggle. I wish you the best on your next 10 years, spiraling upwards. I’m certain my generation has much to learn from your journey. But I pray that you can be an example for your own generation as well, to find meaning in a world that is suddenly, slowly unfamiliar.

    • jerrycolonna

      Thanks for the thoughtful and kind words, Peter. Years ago I embraced the term elder for myself and, frankly, I like it. It fits me.

  • TanyaMonteiro

    What a great post! The ‘scaling Jerry’ project takes another step up, (am reminded of conversations in Berlin some years back.) Congratulations Jerry to you and your teams,

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