This is an excerpt from Chapter 4 of my book, The Pathless Path. It’s been read by over 50k people worldwide. If you want to read more or purchase the book, head to the book page here.
The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything.
– David Foster Wallace
I had no master plan to quit my job. Even now, several years after doing so, when people ask about my journey, I’m more confused than you might expect. Choosing to leave full‑time work was not a single bold decision but a slow and steady awakening that the path I was on was not my path.
It’s tempting to tell a simpler story. People want to hear about bold acts of courage, not years of feeling lost. On my way toward leaving my job, I never had a clear picture of my next step. Experiencing this makes it easy to spot these kinds of phases in other people’s stories and I’ve done my best to highlight them in my writing and podcast.
My conclusion from this is simple: beyond the headlines of dramatic life changes are almost always longer, slower, and more interesting journeys.
Pebble in My Shoe
As I recovered from my health challenges, I entered a phase of restlessness typical of anyone that eventually makes a life change.
A friend, Khe Hy, provides a perfect description of this phase. Fifteen years into a successful career in finance, he walked away to find a new path. However, it took him a long time to make that decision. He reflected, “It definitely wasn’t a sudden realization. It’s a little bit like having a pebble in your shoe, where you’re walking and something is off, and it’s mildly uncomfortable.”
When he got raises or promotions the discomfort would subside but never disappear. Slowly, he became more curious about that feeling and realized that despite his external success, he had become a “passive participant” in his life. Eventually, this convinced him to embark on his own pathless path.
When I returned to work after regaining my health, I had discomfort that could only be described the way Khe put it, as a pebble in my shoe. It wasn’t enough of a feeling to make me do anything dramatic, but it threw me off just enough that I was forced to pay attention to my life in a different way.
As I started to pay attention, I slowly came to realize the reality that I had been living in was an invisible bubble, one of my own creation. I started to push the edges of that reality and wasn’t sure what would happen.
A Daily Reminder
If there are clear boundaries to behavior within a given field of endeavor, then there is also great freedom to adapt and imagine within those lines. These boundaries, however, should always be tested to see if they are actually still real. It takes conscious acts by individuals to test these edges.
– David Whyte
After returning to work, I felt like I had gone through a major transformation, but to my colleagues, I appeared back to normal. I was physically present but detached. Rather than participating in meetings as a good team member, I observed them as a visiting anthropologist. I saw my colleagues with new eyes. Are they happy? What kind of pain or challenges are they dealing with? Is this how they want to be spending their time?
Once you ask these questions there is no going back. Not because of the contradictions in other people’s lives, but because it makes it difficult to live in contradiction in your own life.
This inspired me to act. I wanted to design a career that worked for me and decided to start with a simple commitment, one inspired by a talk from Earl Jones, an MIT alumnus who had shared his leadership principles with my class in grad school. I remembered how he had a list of words that reminded him of what he values, something that popped up on his calendar every morning.
I followed his example and created a daily calendar entry of priorities for my life. First on my list was health. After recovering from my health challenges, I would do anything to stay healthy. Next, my head told me to list “career,” but my heart told me to list it last. This simple decision was my first conscious commitment to exploring the possibility of a life not centered around work. My final list included four items: health, relationships, fun & creativity, and career. Since 2013, this list pops up on my phone at 8:30 a.m. each morning.
Staring at those four items, in that order, was scary. Without knowing it, I had embraced a question that would shape my decisions: “How do you design a life that doesn’t put work first?”
The answer, my dear reader, is simple. You start underachieving at work.
You stop setting an alarm and you cancel morning meetings because the energy gained is worth fighting for. You start working remotely on Fridays without asking because the extra 24 hours with your grandmother is worth it. You start taking naps at the office because there’s a nap room and someone has to use it, right?
I felt like a rebel, like I was doing something wrong. At the same time, I had the sense that taking ownership of my life in this way, especially to prioritize my health, was something worth doing.
Instead of being consumed with thoughts about work and my next step, I had time to continue to experiment, and in the space that emerged, a creative energy entered which started to become a central force in my life.
