Wonderment Is The First Passion of All
- Mar 11
- 6 min read
Updated: 23 hours ago
I was sitting at dinner with a group of entrepreneurs when someone asked a simple question: What was the greatest lesson you learned during your last big adventure?
Without thinking, I answered, “I learned how to play.”
In September 2013, I had just left Google after nine years and accepted a role at a little-known startup in San Francisco called Uber. Leaving Google felt like stepping off a moving train. The culture had become second nature to me. The perks, the order, the predictability, what past employees fondly referred to as “Googliness,” had formed the rhythm of my working life.
Uber was something else entirely.
When I arrived, the city itself felt louder, faster, sharper. Inside the office, there was a restless current of energy. People moved between rows of desks, phones pressed to their ears, conversations unfolding across screens and tables. We sat in long lines with our computers back-to-back. There were no views of the park and trees, no cubicles, no colorful bikes parked outside, no help-desk tickets, no cafeterias or massage tables. The infrastructure of comfort I had grown accustomed to was nonexistent.
On my first day, my computer was still in its box. Wires trailed across the floor. The person who had vacated my seat had left behind an empty soda can. Boxes were stacked everywhere. I had lived through similar environments before at Inktomi during the dot-com era, yet somehow it felt like a distant life.
Something in my body resisted the environment entirely. I missed my routine, my short drive south on Highway 101, the familiarity of structure. Even lunch became an ordeal. I wandered the streets, trying to decide where to eat. I felt strangely helpless, as though the competence I had built over the years had suddenly evaporated. I had amassed all these skills and experiences, yet somehow they seemed irrelevant.
A month passed like this. I struggled through the days, learning the company's rhythms. I had spent many years exploring the city when I first moved to the Bay Area, but it didn’t matter. I felt like a foreigner in this unfamiliar space.
I had been hired to make sense of things, to build structure and systems as I moved along. That was difficult, especially because most of the time I had no idea which direction I was heading. Had I gone rusty? Had I forgotten how to do this? Back at Inktomi, I had been scrappy. I had no idea what I was doing then either, but somehow being in my twenties gave me the right to be thoroughly confused, and everyone just called it growth.
Then one afternoon, I left work early, exhausted and quietly defeated. I sat on the back deck at home while my son played in the yard. And then the realization hit me. What I had been missing in my new environment was not competence, intelligence, or experience. It was the ability to play.
Startup environments thrive on experimentation. The constant iteration, idea flow, and pivots can be overwhelming for anyone arriving from a structured organization. What may appear nonsensical from the outside often makes perfect sense to the people living inside that cycle of experimentation and discovery. The moment I shifted my mindset from resisting the chaos to exploring it, I began to adapt. I began to see differently.
Long before he became the world’s most famous physicist, Einstein experimented with ideas inside his imagination. He called these mental exercises Gedankenexperiments, or thought experiments. As a teenager, he imagined chasing a beam of light through space. If he could catch it, he reasoned, the light would appear frozen.
But light cannot be frozen. That paradox led him toward one of the most revolutionary insights in modern physics: if the speed of light could not change, then something else must. Eventually, Einstein realized that time itself could change depending on the observer, a realization that laid the groundwork for the theory of relativity.
Later researchers attempted to locate the source of his genius in the structure of his brain. After Einstein’s death, pathologist Thomas Harvey removed and preserved the organ, slicing it into hundreds of microscopic slides in hopes of discovering the biological roots of brilliance. Some unusual structural features were eventually identified in Einstein’s parietal and prefrontal regions, yet the deeper mystery remained unsolved. The essence of his creativity seemed to lie somewhere beyond measurement.
As Einstein himself once wrote on a blackboard in his office, “Not everything that counts can be counted, and not everything that can be counted counts.”
Artists understand this principle as well.
I remember the first time I encountered one of Adams’s photographs of Half Dome. It hung in an office at Inktomi. Someone had purchased the print for their new workspace. I stood in front of it longer than I intended, unable to pull myself away. The photograph was simple black and white, granite and sky, yet it held a quiet intensity that made it impossible to ignore.
Years later, I traveled to Yosemite. When I first saw Half Dome in person, I immediately recalled the photograph. The mountain was far more overwhelming in reality. The sheer scale of the granite face, the subtle colors in the stone, the vast blue sky above it. It was late summer, and the light had begun to soften toward autumn. The leaves had lost the brightness of spring. Dust from the dry season had settled across the valley.
Later, I learned what Adams had gone through to capture that image, waiting for the right light, adjusting filters, experimenting with exposure until the scene matched the vision in his mind. The entire process required patience, openness, and a willingness to remain still long enough for the environment to reveal itself. That realization mirrored what had happened to me.
I did not rediscover some lost inner child. Something more interesting occurred. My mind opened to new possibilities of perception and interpretation. Rather than remaining an observer, I placed myself inside the experimentation itself. Adapting is not simply getting used to things; it is learning to move with them.
A favorite quote from Bruce Lee captures this perfectly:
“Empty your mind, be formless, shapeless—like water. If you put water into a cup, it becomes the cup. You put water into a bottle, and it becomes the bottle. You put it in a teapot, and it becomes the teapot. Now water can flow or crash. Be water, my friend.”
Life had handed me a new environment, a new product, but I had been trying to operate within it using past assumptions. I had to shed those assumptions. Embrace the new product and become a super user. Dog Food.
I often get asked, “How did you do it?”
My answer is simple. Just as Adams allowed the landscape to shape his photograph, and just as Einstein placed himself inside his thought experiments, I had to place myself fully inside the startup environment. Only then did the work begin to change.
I began creating systems to solve problems more quickly. Prioritizing tasks felt like solving a Rubik’s Cube, tracking the many moving parts while predicting how each move might land and preparing alternatives in case it didn’t. I became the airport control tower, managing the traffic of ideas, decisions, and competing priorities. Yet, like a kid on a playground, I moved from one challenge to the next almost effortlessly. Some described it as “magic.” In truth, that is what wonderment often feels like.
I began moving more intuitively, drawing on both my intrinsic and learned skills. Failures occurred frequently, but they became signals rather than setbacks. I adjusted the course without lingering on what had not worked. As the environment expanded and contracted, so did I.
Modern entrepreneurs recognize this pattern as well. Eric Ries later described it through the Lean Startup methodology. At its core is a simple cycle: build, measure, learn. Start with a problem. Create a minimum viable product. Observe what happens. Adjust based on real feedback. The process may sound technical, but fundamentally it is structured curiosity.
For builders, explorers, and entrepreneurs, wonderment is not nostalgia or naïveté. It is the disciplined ability to explore unfamiliar environments with openness and curiosity long enough to discover patterns others overlook. Sometimes the difference between staying stuck and discovering something new is simply the willingness to step into the environment and begin experimenting.
And in the end, wonderment remains what Descartes first described it as: the passion that allows us to see something new and extraordinary, even when, moments before, we saw nothing at all.
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