Jon Versus the Volcano
Home—is where I want to be.
But I guess I’m already there.
— Talking Heads
It seemed like the perfect day to hike up a volcano. But as we swallowed the last few bites of our pack-lunch the skies opened up. The gentle dirt path we’d been hiking up the last few hours was instantly transformed into a rapidly flowing river of Central American mud. We probably could’ve waited out the storm before heading back to the lodge. We probably should’ve. But we were 28 years old. So we made a run for it.
It was one of those experiences that starts out awful but becomes wonderful; awful for as long as you try and control it, wonderful when you finally let go. After a few minutes of repeated tripping and falling, I found my stride. If I lifted and stepped with just the right amount of force I could stay near the surface of the mud river, a kind of surf-walking. Pull too hard and my shoes were summarily sucked back down—and more than a few times pulled clear off—by this surprisingly sticky stuff. My traveling companions discovered it too. There was only one way to do it. And then the physical surrender turned to a mental one. My mind started to wander, freed up by the rhythmic monotony of motion. I started to feel how much pain I was actually in.
The pain was not in my legs. It was in my life. The year was 1999, and I’d graduated from law school the year before. I was one year into my first real “career”—slaving away in the bowels of a large, prestigious Manhattan law firm. I was drawn in by the money and the high stakes. When I faxed a copy of my first paycheck to my grandmother she called me a minute later to let me know it must’ve been a clerical error and that I should just keep quiet and hope they didn’t notice.
I loved the negotiations, the intellectual challenge of organizational structure, high finance, and the opportunity to learn from people at the very top of the game. But the personal price was impossibly high. Everyone around me was miserable. There were unbearable tyrants in the corner offices. But, like every other business I’ve ever come across, this one was mostly filled with kind and dedicated people trying to make the best of a tough situation.
The problem was the inhumanity of it all: the unrealistic expectations of leadership; a team of people who might otherwise be friends forced to compete with each other over resources; a toxic mix of power and unconscious behavior that left people feeling like they didn’t matter, that they didn’t have a voice, and that the only way to survive was to put their heads down and bear it. It was a profitable business. And a human disaster area.
That law firm was an extreme workplace in one way. But, as I would come to learn over the next few decades, when it came to the things that really mattered—to the emotional world where human beings live—it was far more the norm than I ever would’ve imagined.
But I didn’t have the life experience to know that while we were sliding down the volcano. The experience I had was far more simple: I was single, stressed-out, and depressed. And while I was no authority on souls—my family’s bible was The New York Times—I was certain that mine was seriously adrift. Somehow, in this one moment, I realized that continuing down the road I was on was no longer an option. I had to leave. I was still young enough to not worry too much about what would happen when I did. We were halfway down the trail when the words reached my lips.
“I’m done!” I threw my head to the sky and screamed out loud into the torrential rain. My very own Shawshank moment. I continued on with my personal pep talk. “I can’t spend another day pretending that this is okay. Everyone I work with is miserable. And nobody is doing anything about it. There has got to be a better way. I’m going to walk into Doug’s office on Monday morning and give my two weeks’ notice.”
Monday morning arrived. I was back at work and it was time to put my new-found resolve to the test. Quitting meant telling the boss—the senior partner in my department and one of the “Top 100 Lawyers in New York” (yes, that’s a thing). He was a small man and scary as hell. The screaming, brutish, Napoleon type. He was not what I would call a Good Authority.
I walked past his office three or four times, trying to work up the nerve, his secretary eyeing me and wondering what this was all about. Finally, I knocked on his open door. “Come on in,” he said, in a friendly tone that more than a little took me by surprise. “What can I do for you?” he asked.
“I’ve decided to leave the firm.”
And with those six little words, all of a sudden we were equals. Just two guys in a room. I wasn’t afraid anymore.
“I’m not happy. I don’t know what I want to do with my life, but this isn’t it.”
“Is there anything we can do to change your mind?” he asked with a curiosity I had never experienced with him before.
“No, there really isn’t. I appreciate you asking, but it’s time for me to go.”
“Do you know what you’re going to do?” By now I could tell that half of his mind had moved on to the next task on his list.
“I’m going to Vermont to do a week-long meditation retreat.”
As he shifted in his chair I could tell that the answer made him uncomfortable. He told some bad joke to break the tension, I laughed politely and walked out. It’s amazing how the authority figures we idolize crumble the moment we stop holding them up. It wasn’t the last time I’d learn that lesson.
I signed up for eight days of silence. Voluntarily. I pondered the wisdom of that decision as I pulled onto I-91 for the four-hour trip north to Vermont. “Jonathan, what are you thinking?” I muttered to myself in a variety of different voices. “Go home. You don’t need to do this.” I managed to stay in the car. Amidst the grueling torture of that retreat—eight days with nothing but my thoughts—something happened. It wasn’t enlightenment.
But it was a profound experience—an experience of myself. Not who I wanted to be. Not who I thought I should be. Nobody special. Just me—bones and flesh, thoughts and emotions coming and going. It was beautiful. Better than any drug—and I’d tried more than one. In that moment I made a decision, as much as you can decide anything long-term when you’re 28, unemployed, and single. I was going to ride that self-discovery train as far as it would take me.
I spent the better part of the next decade doing just that. I had jobs and ventures to pay the bills. But my heart was in the search. I went on more and longer retreats. I travelled to high mountains in faraway places to look for wise teachers. I moved to San Francisco, which, to a Jewish kid from the New York suburbs, was the mecca for all things weird and leading edge. I helped to start a renewable energy business. I dove headlong into the world of alternative healing: studied to be a yoga teacher, trained in somatic psychotherapy, and considered going back to school to get a master’s in psychology. I joined up with some friends to create a nonprofit that teaches meditation and mindfulness to kids in juvenile hall. I fell in love and had the first real long-term relationship of my life.
Along the way I found a few things that I was genuinely good at and could have made a career of. But I still couldn’t shake that feeling. The one that was sure that whatever I was supposed to be doing with my life, I hadn’t found it yet. It turns out, I didn’t need to. It was about to find me.
In 2011 I came across an opportunity that I couldn’t resist. I took on the CEO role at EMyth, the business coaching company behind the well-known book. The owner had decided to relocate the company to Ashland, Oregon, the small town halfway between Portland and San Francisco where I was living. Finding myself at the helm of a name-brand coaching company, with a mandate to revitalize the culture and take things in a new direction, was the kind of big city opportunity that I never imagined I’d find in a town known primarily for its annual Shakespeare Festival.
The first few years were a thrilling and wild ride. I was still pursuing my own personal work on the side,