Building Castles and Slaying Dragons

“Why are you so obsessed with this good man thing?” she asks, her voice tinged with a mix of fear and frustration. Perhaps she’s tired of my loss. Perhaps she sees in me what I fail to see and, so, is frightened by my struggle.

What is a good man? I turn the question over and over again in my mind. The question echoes and reverberates in the hearts of many of my clients.

A good man takes care, answers one voice; that of my father, perhaps, or my grandfather? Perhaps it’s the elders who’ve helped raised me to adulthood. A good man, as I’ve been repeating lately, builds castles, slays dragons, and, if he’s opened his heart, tends the hearth–building a fire against the cold empty night so his loved ones are safe, warm, and happy.

On a walk on a hill in Marin (thanking God for the gift that is California), I met an ancient one, toppled by age, blight, and wind. Stopping in my tracks I realize: here lies a good man.


If, at the end of my days, as this current meat-bag starts its inevitable transition to the Earth that birthed me, I can lie as majestically about the soil as this Elder, I’ll know that I earned my manhood.

His body ragged with the scars of actions about which he may not have always been proud but resting in the knowledge that for 50, 60, or maybe 100 years he grew into his purpose: sheltering others, providing them a respite from the glaring sun, the toppling wind, and the painful vagaries of life.

Gnarled and twisted by inaction, decisions taken and not taken; scarred by selfishness, with limbs stretched by acts of kindness and gentleness, I wish to end my days stretched out on the side of a hill, welcoming the slow decomposition of my anxieties and my flesh into nourishing earth.

Knowing this is possible strengthens me. I can withstand the demon that mockingly caws that I am unworthy; hissing that my failures outweigh whatever good I have done. The relentless voice which has whispered to me all my life.

Last week, in the middle of our last CEO Bootcamp, I had an epic dream–the kind that teaches you about yourself. I returned again, as I have written before, to a past job, the place where I became an adult and a father.

Working this gift from my innermost being, I found myself articulating fiercely my purpose. I found myself feeling an egoless pride in the man that I’ve become.

I have been taught, and so strive to teach, that one must be unattached to the outcome. We must resist the temptation, I warn, to merge Self with the company, the goal, the job.

But we must also be unattached to our actions. Yes, we bear responsibility for our actions–we are the owners of our own karma, Sharon Salzberg reminds me, and our happiness is the result of our actions and not our wishes. We must know, too, and own those actions–especially those that have harmed others. But liberation lies in separating our sense of worth from those actions. Feel the remorse, she teaches, but drop the ego-aggrandizing guilt.

I want then to be reborn with the bright promise of young irises. deathandbirth2A good man, I see, takes pride in his aspirations without using failure to achieve those aspirations as evidence of his unworthiness, un-lovability.

Last week, as the Bootcamp wound down, one camper–harkening back to my stated aspiration from the first night–shared his conviction that we had saved some lives that weekend. His words toppled me and I wept. It’s a good thing to save lives. It’s also sacred to simply try.

Still Standing Still

Years ago, I wrote that founding, running, and working in a startup can often feel as if you’re standing still while your hair’s on fire.

I wrote that phrase offhandedly, as if it were merely a funny little image to help explain the intense sense of panic of life in a startup.

Years and hundreds of conversations later, the image feels even more true. Back then, it evoked the feeling of combining the sensation of not making progress with the urgent, frantic panting need to move at all costs.

Yet as I’ve grown I’ve come to know that the exquisite pain of standing still isn’t limited to entrepreneurs.

The image first came to me when I heard David Wagoner’s exceptional poem, Lost. The opening lines haunt me: “Stand still/The trees ahead and bushes beside you/Are not lost.”

Sitting on my cushion this morning, working with a powerful instruction from my teacher Sharon Salzberg (and the instruction was to recall that “All thoughts are empty.”) I watched as stars blinked out and the sun rose. And I thought, “The stars are not lost.”

As often happens, themes and ideas work their way through the fiber of my being. I knead concepts and teachings, over and over, working to discover their truest meanings. Recently, for a talk on surviving life in a startup at the Pioneers festival in Vienna, I revived the image, kneading once more.

I think it’s found way back into my consciousness because I need to hear the message again. My current life feels an embodiment of the notion that, to borrow a phrase from my friend the Buddhist teacher Emily Horn, consciousness is so turbulent.

When I first wrote of Standing Still While Your Hair’s on Fire I saw the juxtaposition as an expression of utter panic. Now, though, I understand it to be advice, a prescription for how to respond when you feel all is lost. Seen this way, it’s perhaps the most difficult to implement instruction I’ve ever received: Do nothing. Stand still.

I think this is really what Waggoner was getting at in his poem:


Stand still. The trees ahead and bushes beside you
Are not lost. Wherever you are is called Here,
And you must treat it as a powerful stranger,
The forest breathes. Listen. It answers,
I have made this place around you.
If you leave it, you may come back again, saying Here.
No two trees are the same to Raven.
No two branches are the same to Wren.
If what a tree or a bush does is lost on you,
You are surely lost. Stand still. The forest knows
Where you are. You must let it find you.

Re-reading those lines, I feel my panic-filled body resisting: “Stand still? Are you kidding me?,” my heart races. “Let the Forest find me?” And then the real fear creeps in: “What if it doesn’t come to look for me?”

Despite my panic, I know it’s true. The surety of that knowledge is the gift I receive from my clients. I see their transformations, feel their growth with a wonder that moves me to tears.

There’s an email thread, for example, among some of the folks who attended our June bootcamp in Tuscany. It contains some of the most heart-felt and heart-wrenching expressions of deep transformation I’ve ever read.

A few weeks ago, I watched a client speak at a company all-hands and weep with joy and broken-hearted love for his family and for the gift that are his colleagues. I saw dozens of eyes soften and know that this place is a place where it’s safe for humans to be human.

At the talk in Vienna, a young man came up to me. As so often happens for a speaker, folks had come up to share an observation, express thanks or disagreement. But this young man stood apart. And through the crowd of about ten in front of me, I saw his eyes. Red, swollen–the pain so evident. I pulled him aside, gathered him into a sheltered corner and he said, “Jerry…what you said…it’s…” and he broke down. We both wept. A total stranger, with English as a second language, he collapsed into my arms, and I whispered, “You’re not alone. You’re not alone. You’re not alone.”

Oh my…this work…this work I and my colleagues do, is such a precious gift. Coaching, workshops, bootcamps–really it’s all about learning to stand still; the steps necessary and being with the fear that it invokes. In this way, perhaps the forest may find you.

Our next bootcamp will be February 25 through March 1. Come join us and let the forest find you.

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

Being Fierce

I’m amazed at how much fear is a part of my life.  Even more startling is how clearly I see that grip when the fear loosens its hold and I’m lighter, less-burdened.

I’m also amazed at how well my unconscious feeds me what I need to hear, especially in times of deep transition and fear. It’s like when that mysterious woman speaks to you in a dream, telling you the thing you need to hear most. Or when the right words whisper to you as the breeze shakes the aspens in a walk outside of Bozeman.

These two observations came to me as I thought about the notion of being fierce. Months ago I was asked to give a brief talk and, after getting over the initial shock of being asked to speak briefly, I zeroed in on one aspect of leading which I found most difficult: having difficult conversations.

At the time, I didn’t want to admit to myself that the difficulty isn’t merely for my clients but for myself as well. In that talk (embedded below), I spoke of our tendency to avoid fierce conversation…with others, of course, but with ourselves as well. But as teachings tend to do, the notion–what I called “Being Fierce”–began to work on me.

In the first variation of the talk, I expressed the wisdom I’d learned from my therapist; as a way to cope with my migraines–something that had plagued me my entire life–she taught me to ask myself, “What are you not saying that needs to be said?” Identifying that and, importantly, saying it, freed me from the worst of my headaches (to say nothing of releasing me from back and stomach problems).

After the talk, though, it was clear the universe wasn’t done with me. I was asked to speak at the Wanderlust festival in Aspen. (Yes, me, a former VC, a former employee of JP Morgan Chase, talking to a bunch of yoginis at a festival celebrating so many things that my former JP Morgan-self would have found challenging.) As I was reviewing my notes for that talk, I had to admit there were other questions worthy of exploring. To that talk, I added two additional questions: “What are you saying that’s not being heard?” and “What’s being said that you’re not hearing?”

When I shared those three “magic Ninja move” questions, I could feel their correctness. Eyes grew wide. Bodies settled into place. And we, as a group, connected deeply enough that one woman was able to cut through my “I’m-the-presenter” persona/screen to ask me a question that made me cry (see, I’m not the only person with the superpower that calls forth tears): How do I react when I encounter a fierce woman? I said, “It depends. If the fierce woman reminds me of my mother, I have one reaction. But if the fierce woman reminds me of one of my sisters, than I have another.” I broke down when I thought of one sister in particular.

I’ve been walking a bit here in Bozeman. Big Sky is having at me with abandon. I came here from Boulder where I’ve been spending most of the summer, on sabbatical, prepping myself for the next transitions in my life: personal as well as professional. 2014-07-28 18.39.26 I came here to sit in the grass and, eventually, came to another observation. My late obsession of teaching about being fierce hasn’t merely been for my clients or those others who’d share a few hours with me. (Or, as some hardy souls have already done, share a few days with me at one of my bootcamps.) It’s been for me as well.

Sitting on a hill, staring off into the endless horizon, I recounted the half dozen or so fierce conversations I’ve had to have over the last month or so; each more frightening than the last. Each months, sometimes years, overdue. I suppose you know you’ve discovered the truest teachings when they rip you apart as surely as they rip apart the other. When the distinction between “teacher” and “student” is torn and we stand together, broken open by the fearful act of being fierce–when it’s as hard for you to say as it is for the other to hear–you know you’re speaking truth.

Thanks Bijan Sabet and Danya Cheskis-Gold for inspiring this talk and creating the goodness around supporting deep important dialogue.

Up and to the Right

I have a chai; he has a cappuccino. We sit outside, at the metal mesh patio tables, as the coffee house is about to close.

“I can’t decide the path: Taoism or Zen. It’s all so confusing.” He’s in desperate need of a haircut. I’d cut his hair myself if I had scissors.

We pause. Sip. Look west, watching the sun.  His search for a spiritual path is a proxy for the larger existential questions: Who am I? What do I want from this life?  I’ve nothing to say that can ease his pain. I’m helpless.

“I want to strip everything away,” he continues. “Anything that’s not me, to the bare essence of me, just so I can figure out what path I should take.”   I know that feeling.

Years and years ago–ages ago if, as I do, you see each interminable hour as an eon-like day filled with desperate pain between then and now–I knelt before Pema Chodron, pleading for her to tell me the path, the way, the steps I should take, to take me out of the pain. Then she lovingly tapped my hand, telling me about the pathless path. It makes sense now; then it left me bereft.

“You seem to want to know that you’re making progress, that there’s path and that you’re on it,” I offered. He nods and his bangs shake, the boy so evident despite the man’s body.

“I can’t tell you how much I wish I could tell you. All I can do is point out what I’ve seen. I’ve seen you find a teacher, follow them down a path, feel what you felt, learn what you learned. And then I’ve see you pause, sometimes doubling back and re-directing yourself, sometimes moving backward.”

He’s watching me. He knows I’m speaking from my heart, telling my story as much as his. “And I’ve seen you plateau, stand still.” Then I make my point, “And to me, it’s seemed that that is when the next teacher, the next path, emerges. It’s never been when you worked hard to find it. It’s never been when, head in hands, you gnashed your teeth.”

Relief washes over him.

“It’s odd how we are all so desperate to move up and to the right. We become convinced that any motion that isn’t straight, direct, up and to the right is somehow not part of the path.”

Screen Shot 2014-05-18 at 10.17.54 PM

What if being lost is part of the path? What if we are supposed to tack across the surface of the lake, sailing into the wind as much as with the wind at our backs?

I share the story with my partner, Ali. “Yes!” she blurts out, elongating the S. “Leslie Feist has this brilliant song with an incredible line…”

A map is more unreal than where you’ve been

Or how you feel

Opening email this morning, there it is again: the wish for a map, for a path, for direction.

“Dear Jerry, I am looking to define an meaningful next chapter which meets my personal, professional and practical goals,” one inquiry begins.

And another…”I’m not lost, but could sure do with a point in the right direction (and a kick up the ass!).”

And then this:

“Dear Jerry…I was introduced to your site just last week…I just came to it today, and I’ve been crying for the past two hours since reading your work. I could say I’m not quite sure why, and I could a list a hundred reasons…I’ve done a ton of this type of work. But I’m skimming the surface of the ocean.

Your comments on being a warrior struck me the most…I finally think I’ve brought myself to the point where my hand is on the door knob, but I still don’t know how to open the door or cross the threshold. I need help…But I really don’t know if I can actually make it anywhere, or if I’ll just always be wishing for something and never actually create.”

We all want it: movement that demonstrates that our experience is meaningful, that it’s taking us someplace, any place better; a place where we are smarter, richer, healthier, less afraid, more secure. Up…and to the right.

We live in a culture that says anything less is failure. Up and to the right, we’re told, is where the happy people are. That’s where the people who never fear, never fail, never struggle live on bonbons.

Our economy is driven by the sense that here–down and to the left–is awful and if we buy the right soap, drive the right car, build the right company, love the right way, we’ll be safe and loved and happy for ever and ever. And ever.

We look to those who seem serene, content–the embodiment of up and to the right–and fail to see the struggles they lived through. We place into them our wishes and our expectations of reaching that point where all things are at peace and we never ever smell of body odor.

Everyone else’s journey is so much easier. Every else’s business is so much more successful. And if only someone–you–would give me a map, then I can get there too.

But a map is a poor substitute for a life lived. The truest guide isn’t the mind of a guru but your broken, scared, and lonely heart. I just wish broken-open hearts weren’t so damned painful.

The irony, of course, is that up and to the right, as appealing as it is when we’re down and to the left, is a place of separation. It’s a place where, were we to achieve it at all, we’d find ourselves found, perhaps, but utterly alone.

When I catch myself wishing for more than incremental progress that’s directionally correct, I remind myself of the companionship I’ve discovered in this murky, mucky place, down and to the left. I belong to this place, for this is the place where, as David Whyte writes, “I ask my friends to come, this is where I want to love all the things it has taken me so long to learn to love.” Me and my broken-hearted friends, we belong here.

 For S. Thanks for sipping in the sun.

Our First CEO Bootcamp: This Being So, So What?


“In these bodies we will live, in these bodies we will die

And where you invest your love, you invest your life.”

Mumford & Sons, Awake My Soul

One of the great gifts of our first CEO Bootcamp came for me. It was a reinforcement of something I never tire of hearing: Trust your instincts.

Just hours before our first night’s gathering, when my partners Ali, Sam and Michael and I would greet the participants, the campers, I was still working out what I was going to say to start things off. I sat in our lodge, by the cold fireplace, thinking by typing.

For days Mumford & Sons’ Awake My Soul had been playing in my head. “It’s a virus, “ I told Ali as we drove to Devil’s Thumb Ranch from Boulder, “it’s taken over my CPU.”

I knew we had to make room for the soul.

photo 3

I also knew that, in setting the stage for what was to come, I had to lean into the reality of the participants as co-creators. We had to create the space for what was true for them in their lives to emerge while simultaneously holding a structure, a container. I realized that implicit in their questions were the answers.

Then, as I was typing and thinking, an idea popped: have the campers read the questions they’d written on the applications.

After a few minutes of greetings, we settled into our chairs in a circle. I joked about feeling guilty about being in such a beautiful place (and, more seriously, feeling guilty about taking time away). Then we passed around a random and anonymous set of questions and asked each person to read their questions aloud to the whole group, placing the questions—if you will—into the center of our circle.

photo 2

Magic happened when we’d finished reading aloud; one camper raised his hand to add another question: “Is anyone else having an anxiety attack listening to those questions? I could have written every one of them.” He paused and started to cry: “I didn’t even know I was holding those.”

Magic happens when you listen to the song that’s embedded itself into your head, into your heart.


The feelings in the room shifted, settled, eased into the Earth and we knew we were onto something.

Earlier I had described our bet:

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This was the bet of the weekend and I was watching it unfold.

I believe fervently believe in that bet, that calculation. Time and again I’ve watched as hearts break open and true, authentic leaders emerge. But that process depends on a brave first step: facing the reality of what is and not being deluded by the powerful, seductive dreams of what can be.

Of course this doesn’t mean there’s no role for dreams. We need dreams.

“Ah, but a man’s reach should exceed his grasp, Or what’s a heaven for?” Robert Browning.

But the willful ignoring of what is true is not the same as dreaming. It’s delusion and delusion leads to terrible decisions and, even worse, the destruction of trust. Hence my bastardization of a Zen aphorism: This being so, so what?


And what was so for those campers, what is so for many entrepreneurs, is fear; fearful questions keeping them up at night and fearful imaginings keeping them from their kids’ school play, their spouse’s side, causing them to lose their way as humans.

The first thing to do when we’re lost is to look to the ground and the sky: What is true? What is false? What do I know? What am I imagining to be so? What are my demons and how are they standing in the way?image

The first act of becoming a leader is to recognize this being so. From that place, we get to recognize what skills we need to develop, who we really are (and are not) as leaders, and to share in a way that creates authentic powerful relationships–with peers, colleagues and even our families. Grant us leaders who can do this and we just may create institutions that are less violent to the self, our communities, and our planet.

The Camp unfolded and I watched my allies, Ali, Michael and Sam, with wonder and awe. It felt like we were playing jazz, never quite sure whose riff would end when but comfortable relaxing into the not-knowing of the music.

As the Camp unfolded, I realized again just how fortunate I am. I get to bear witness to extraordinary people finding themselves. I get to live out the life I was meant to live all while watching people discover the lives they were meant to live.

When we started planning this Camp we had vague notions of doing this several times with different cohorts (the coherence around a particular cohort is incredibly powerful). Those notions are less vague. Tired and exhausted at the end of the week, we could barely contain ourselves from launching in and planning more. We’ve already got a “keep me up to date” list for future Camps as well as nascent discussions about doing one in Europe and doing something specifically for a profession.

Regardless of how future Camps unfold, though, nothing will take away from the magic of this first experience. As I said that last day, you never forget your first love. My fellow Campers, you stole my heart.

(Special thanks to Sooinn Lee for her incredible illustrations of the experience. You made the Camp that much more magical. Thanks, too, to our dear friend and inspiration, Parker Palmer. His work inspires, challenges, and deepens the heart and soul of who and what we are everyday.)













Re-creating the conditions of our lives

I believe that, more often than we care to admit, we create the conditions of our lives; the good as well as the bad. I’m not talking about some sort of New Age visualization tactic. That practice may  or  may not work (“There are more things in heaven and earth, Horatio/Than are dreamt of in your philosophy.”). I’m talking about the ways in which our unconscious needs drive us.

For me, my need to rescue, to take care, can feed a manic quality to my work. Despite the Zen-like bearing I can project, the truth is different: the more efficient and effective I am, the more I take on. Couple that with my unconscious somewhat neurotic impulses and I can find myself working at a pace that is harmful to myself and less effective for others. I have to remind myself that speed kills.

So I put myself in the time-out chair. Beginning in July, I officially entered a sabbatical (this despite still working on occasion–I’m incorrigible), which will last until after Labor Day.

There are multiple goals for this period. One is to simply cut back, to feed myself–as I like to say–so I can later feed others. Another is travel-I leave later this week for another visit to rural China, to Tibet, to renew friendships and visit sources of inspiration. I’ll be bringing my 16-year old son Michael and he’ll see why his dad is so in love with a land and its people.

I also want to read and write more.

But, really, I’ll be using this period to rethink, again, the way I manifest my work in the world. I feel deeply connected to this calling: helping people with the existential challenges that arise when we encounter work.

Indeed, few things have given me the satisfaction I experience, the simple joy, of bearing witness to someone having a profound breakthrough on their journey to existential equanimity. I love the nearly audible click when my client’s brain kicks in and they understand viscerally as well as intellectually what it means to lead. It’s breathtaking.

As I’ve written before, I want to have greater impact. Over the last few years I spoken more, led more workshops, facilitated more group dialogues and worked more closely with whole teams. This spring I had the joyful satisfaction of speaking about the crucible of leadership to a varied group of entrepreneurs and loving each one of those who allowed their hearts to break open to what is: the sound and the fury of that crazy-assed job, being a CEO.

I also realized the gift of working with my friend Parker Palmer to lean into the difficult vortex of depression. (Thanks, Parker, for that gift.)

But something wicked this way comes (boy, I’m in a Shakespearean mood today).

A few weeks back, a long talk I did with my friend Jason Calacanis was posted and became mildly viral (Side question: Is it possible for something to be sort of viral? Or is viral-ity like pregnancy? It is or isn’t? I should ask Seth.).

In that conversation I casually mentioned an idea I’d been marinating on with a few folks: a retreat, an extended workshop, to help folks in the struggle of becoming a CEO. The idea was to host a small group of selected people coming together to focus on the pragmatic aspects of the job while exploring the body and soul techniques available to enhance their resiliency. To get even more prosaic: I want to facilitate a group of first-time CEOs becoming startup warriors.

(In various spiritual traditions, the notion of warrior refers to the ability to face life as it is–head on with dignity and equanimity.)

That casual reference resulted in hundreds of emails. We hit a nerve.

The theme of the CEO Boot Camp we’ve designed is “Reboot your leadership; reboot your life.” The plan is to spend three and half days together exploring, learning, challenging each other. “It’ll be a success,” I told a friend, “if, at the end, what emerges is a tight-knit group of peers supporting each other with humor, skill, and courage.”

This week, we open the doors to the application process.

When I began thinking about this post, I thought I’d simply tell the story of how this immersive workshop came to be and how it seems to fit so well into the ways I’d like to take my work–deeper and with more impact.

But when writing, I realized that, as with so much of this inner-directed work, the challenge is there for me as well.  In a sense, and without intending to, even the process of collaborating on this project has caused me to reboot my own thinking. I suppose, in the end, this is what I was searching for all along: to interrupt the conditions and patterns that unconsciously drive my life and, once more, raise my awareness and choice. In doing so, I raise the chances of creating the conditions I want in my life.

So, if you join us, we’ll be rebooting together.

The Hand of A Friend

After hours of careful listening, my therapist offered
an image that helped me eventually reclaim my life. 
“You seem to look upon depression as the hand
of an enemy trying to crush you,” he said.
“Do you think you could see it instead
as the hand of a friend, pressing you down
to ground on which it is safe to stand?”

Parker J. Palmer Let Your Life Speak

I met Parker Palmer long before he met me. It was March 2002. I was on a plane to Arizona and I had in my carry-on some things I’d meant to read for a while. Among them were two pieces given to me by my sister Ann: When Things Fall Apart by Pema Chodron and a magazine article.  Ani Pema’s book became my gateway drug into Buddhism–but that’s another story.

The article was an excerpt from the book, Let Your Life Speak by Parker. I knew others had written openly about their struggle with depression, with difficult challenges of the heart but Parker’s grace, simplicity, elegance, and care, spoke to me. His words released something from deep within me.  I wept.

Several weeks before I’d stepped out of a meeting in lower Manhattan and stood just shy of the still-smoldering wreckage that was Ground Zero and wanted to die.

It hadn’t been my first encounter with suicide. As I often add when sharing this story, “Hello darkness, my old friend.” But thankfully I called my therapist instead. And thankfully instead of giving in to my wish to be put in a hospital, she suggested I get myself to Canyon Ranch for good food and daily massages.

A little later I was weeping in seat 7D, wondering who was this man who spoke so fiercely, with love and heart, and with no trace of maudlin self-indulgence? Ten years later–my life radically, lovingly different—I found myself on a call with Parker, laughing and knowing and laughing some more.

Parker and I came together through my teammates at Cojourneo, Kevin Friedman and Dan Putt. Parker and our good friends at the Center for Courage and Renewal have crafted a workshop built around the principles underlying his Healing the Heart of Democracy. The partnership strengthened and blossomed as this year began.

Then, just weeks after Aaron Swartz, Jody Sherman killed himself. As with so many in this industry, Jody and I had crossed paths a number of times. The first was 17 or 18 years ago when he joined Lycos–one of the first companies I’d helped birth into being. The last was in 2012  when he attended a workshop I’d given on behalf of the guys at Venture51. In that workshop, Disappearing into the Fire: Surviving the Startup Life, I tried to address the emotional demands of this delusional thing called entrepreneurship.

I remember the end of that day, my voice raspy and tired, I paced the room asking in desperation, “What are we doing to ourselves? What are we losing when we pursue this magical, impossible task of building a company?” I wish I could say that I had looked into his eyes when I’d asked those questions. I hadn’t. But later, in that Jody way, he grabbed my hand with a firmness that felt even then a little too tight and said: “Thanks Jerry. That was great. Maybe we can grab coffee sometime and catch up.” I nodded and headed for water.

A distraught client emailed me the day after Jody died. So many people were hurt by the news–whether or not they knew him. I tweeted, emailed, reached out to friends. I wrote to Parker.

My request was simple: Help me help them. We decided the best way to respond was to embody what we believe: that speaking about the existential difficulties, being authentic even in our collective guilt, pain, and fear, is–as Parker coined it in Let Your Life Speak–Leading from Within.  We would have a conversation about the ways in which this merger of self and work exacerbates the pain as well as Parker’s notion of the Tragic Gap. We’d invite others to join us.

The conversation, sponsored by Cojourneo and the Center for Courage and Renewal, is in two parts: the first will be via video chat on March 20 at 7:30 p.m. EDT. You can register for that here. The second will be in person on April 19 at 2 p.m. at Naropa University in Boulder; register here. Both are free.

I have no illusions about our coming up with solutions. I have my theories about why I think the entrepreneurial path is so damn hard but, really, I have no answers. And I’ve written plenty about those dealing with the Monsters (One client said last week, “Um, that’s all you ever write about.” Not true! Okay…so maybe it is true but still…). I just know that there’s something powerful in the simplicity of friends coming together, to listen and to hold each other.

What little I know about the Quaker wisdom tradition comes from my friend Parker. His vision of a Circle of Trust—which comes from that tradition–is such an exquisite example of the opportunity, the responsibility–before all of us: to be the friend whose hand holds another still; to make it okay for them to be with whatever is happening. Simply that.

And, with a nod to yet another wisdom tradition, it is in fact a heart-wrenchingly beautiful yet difficult and hard gift to be simple.

So we will sit, first on a Google Hangout and then later at Naropa. We will talk and we will listen. We will be together.

Yesterday my son Michael sent me a link to a video of a young poet. Watsky spoke to him. This morning, as I write, I recall Watsky’s deeply personal, deeply affirming observation: “We live in a house made of each other.”

Come sit with us. We’ll build that house.

If a sadness
Rises in front of you,
Larger than any you have ever seen;
If an anxiety, like light and cloud shadows,
Moves over your hands and everything you do.
You must realize that something is happening to you,
That life has not forgotten you,
That it holds you in his hand
And will not let you fall.