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.

I hate waste. Nothing breaks my heart more than how poorly we treat the Earth, and I'm very eager to support leaders working in all facets of sustainability -- waste management, renewable energy, closed loop economy, etc.

A bit about me: I feel more at home in the woods than anywhere else. I co-founded the sustainability committee at FreshDirect. I only buy used furniture. I've green-ified all of my banking and personal finance. I actually wash plastic containers before I recycle them. I aspire to live a zero-waste lifestyle, and I'm absolutely exacerbated by how difficult it is to live sustainably, especially in New York. 

If you're a leader in sustainability looking for a coach, please get in touch.

I am on a mission to change how our culture views the inner world.

Public discourse on today's challenges pertains mostly to the outer world.

What incentives can we give businesses to stop polluting? What laws can we pass to stop racism?

But the hidden questions underneath pertain to the inner world.

How can we transcend our biases? How can we be kinder? How can we align values and actions?

Psychological drag at the individual level will slow progress in all things until we pay attention to inner world and confront what we find — specifically, what prevents transformation and what enables it. 

To date, Western education has failed us in this regard, resulting in an outer world that conflicts with the inner world. Workplaces shun feelings in the name of professionalism, schools focus on standardized tests instead of children's unique gifts, and prisons cause more trauma than they heal. The list goes on. 

What to do?

Generally speaking, the West conceives of self-development in terms of “self-improvement” — acquiring skills, accomplishing goals, and fulfilling your potential. This is important, but not the whole picture. 

Developmental psychologists know a powerful truth: humans can grow through discrete stages of ego development, each with increasing flexibility of thinking, openness to experience, capacity for self-regulation, and integration of more sources of truth.

Given this, I distinguish between two distinct, yet intertwined, forms of development.

Horizontal Development is about becoming more skillful. Run a faster mile, shoot a cleaner free throw, write a better investor update. It’s about improving technique, being more productive, and performing at your peak. “How do I get better, faster, stronger?”

Vertical Development is about becoming wiser. Meditation, shadow-work, and double loop processing (I.e., examining not just the problem, but how you see the problem.) It’s about exposing your assumptions, shifting paradigms, and expanding your sense of self. “What am I not seeing about myself and the world?”

Horizontal Development increases competencies in specific domains. Vertical Development increases competencies that transfer across domains — e.g. the ability to listen, navigate complexity, and see the limits of one’s perspective. Because of this, as we advance through stages of Vertical Development, we gain access to more powerful “Archimedean points” — places to stand and levers to move the world.

I believe that our species’ most existential problems — ecological crisis, mental health deterioration, political gridlock, isms (sexism, racism, etc.) — exist because we lack critical mass of vertically developed leaders to solve them. Ask yourself: Do you think we’ll solve political gridlock by building better spreadsheets, or by becoming better listeners?

Human development is the hidden topic underneath all topics. I believe that it should be among individuals’ highest priorities to attend to their vertical development and among society’s highest priorities to facilitate it on a collective scale.

This means educating people about what vertical development is, and facilitating it. 

As a coach, I do both horizontal and vertical development. I believe that this approach can make your team radically more effective and produce extraordinary business results.  More importantly, I think it can help you become a truly great leader with impact potential not just for your company, but beyond.

Are you in it for the exit? Or are you in it for something bigger?

If you are a leader / founder / VC working on something relevant to the above, please reach out.