When I was 24, I woke up for the first time.
It was at a Lady Gaga concert, during the song “Born This Way.”
I had been a high functioning chameleon for most of my life. I smiled when I was supposed to, got straight A’s in high school, and went to Princeton. I starred in theater and dance productions, sang in an a cappella group, and ran for office in all of my groups. When I graduated, I wondered: should I apply to Stanford Law School? Or, no, maybe Stanford Graduate School for Engineering…
Underneath it all, there was something I never admitted to anyone. I felt I was living a lie.
Lady Gaga's song is an anthem for authenticity, but I felt like a fraud, an imposter, a dazzling house of cards. When she sang, the weight of my inauthenticity crashed into me, and I wept.
I had lived my life in a trance, obsessed with a notion of success that was not my own. I had never asked myself, “What do you really want, Josh?” I had no idea. Apparently I wanted to go to Stanford. Why? For the same reason I did everything else: it would mean I was worth something.
At the time, I was teaching physics and writing to high schoolers. But that night, I told myself that for the first time, I would do what my heart really wanted: quit and become a professional piano player.
There was one problem. I didn’t know how to play piano.
But I was on fire with motivation. I learned some songs from YouTube, auditioned at a dueling piano bar called Howl at the Moon, and got hired as a trainee. Two and a half years later, I opened Howl’s St. Louis location as its Entertainment Director. Later, I opened their Times Square location as a starting performer.
In St. Louis, I learned about the Enneagram. It absolutely floored me. I learned that I'm a type 3, and 3s' whole "thing" is that we lose ourselves by chasing an externally sourced definition of "success," unless we wake up and get back in touch with our heart.
Reading about the type 3 was horrifying, yet captivating. It described in plain terms the inner struggle that characterized my whole life. I felt "seen" from the inside out. It was profound to realize that there were 8 other types that felt as "seen" as me, but in very different ways.
The Enneagram revealed that my private struggle — of wanting so badly to be liked, to be successful, that I would sacrifice my heart on the altar of status, prestige, and "success" — was not just my own. All of my fellow 3s share it. The Enneagram also helped me to see my own worth and to stop compulsively chasing validation. In so doing, it awakened my chief gift — seeing others' worth and potential, and helping them to see it too.
The Enneagram helped me grok that what motivates other people is NOT the same as what motivates me. I had many aha moments about my parents, siblings, co-workers, and friends. It was like having a pair of empathy glasses that brought others’ “strange” behavior into focus.
Before the Enneagram, I used to get incredibly frustrated with people because I couldn't conceive of why they acted the way they did. This made me a bad leader – I led from exacerbation and not from curiosity. I ran rehearsals like a boot camp, trying to “get everyone in line.” But with the Enneagram as a lens, I finally understood what motivated people, and my leadership style changed dramatically. I softened toward my colleagues, and to my surprise and delight, we became a much more high performing team.
With this new orientation, I entered the business world. As the L&D Manager at FoodKick — a grocery delivery startup run by FreshDirect – I was responsible for training and culture. (A lesson I learned was the farce of having a single leader be “responsible” for culture.) I wondered whether my heart-forward approach would be welcome in a traditional corporate context. My guiding questions were: “How can a culture that appreciates people for who they are drive business results? What does it look like operationally?” I rewrote PTO policies, redesigned wage structures, and led leadership development workshops. I learned the power of this approach to achieve business results, but I also learned the challenges of implementing it without full organizational alignment. (See: Reinventing Organizations by Frederick LaLoux.)
After FoodKick, I moved fully into teaching the Enneagram and coaching leaders (mostly founders and VCs) to be the best version of themselves they can be. I love what I do.
In all of my work, I care about ushering in a revolution in our collective way of being — one that embraces a developmental lens, honors inner work as much as outer achievements, and champions love, planetary harmony, and the deepening of our consciousness. I draw inspiration from thinkers like Parker Palmer, Ken Wilber, Peter Senge, Frederic Laloux, Patrick Lencioni, Wendy Palmer, Byron Katie, George Gurdjieff, Krista Tippet, Mary Oliver, and Adyashanti.