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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 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 with individual and group coaching practices.

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


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