The Pathless Path

詳細資訊

I was extremely nervous. As the teacher of my semester-long Chinese language class called my name, my heart started to race. I took a deep breath and began. I shared the story of quitting my job, deciding to move to Taiwan, meeting the woman who would become my wife, starting an online business, and living in five different countries. It was the first time I had shared my story in another language, and as I finished, a calmness swept over my body. It was the end of a three‑month period when I had felt completely alive, spending my time learning, creating, solving problems, and exploring Taipei with my wife.
This would have been unimaginable to me five years earlier when I lived in New York City. I was single, spending my time at work, eating out, partying with friends, dating, and constantly plotting ways to work less or escape work altogether. I was working at a consulting firm making nearly $200,000 a year and working on projects for some of the most recognizable CEOs in the world. I was successful, and on my way to being even more successful.
This was the end result of an obsessive focus on getting ahead in my 20s. It’s a state familiar to many. Study hard, get good grades, get a good job. Then put your head down and keep going, indefinitely. This is what I call the “default path.”
Growing up, I thought making $100,000 a year made someone rich. When I made that amount for the first time at 27, I felt like I had more than I could ever need. Yet I opted into an identity that didn’t accept such complacency. Everyone around me was always moving forward toward the next achievement.
Chasing achievements is what brought me to that New York City job working with CEOs, the final one before I decided to quit. Most mornings I came into the office and sat there struggling to start my day. I watched the people pass my desk and wondered if they felt the same stuckness as I did.
Eventually, I would start my work, helping company boards assess their senior executives to see who the next CEO of the company should be. I read through feedback reports from people throughout the company and created summarized reports of each executive’s strengths and weaknesses. We like to think that once we “make it” we can finally be ourselves, but based on who the companies selected, it was clear that the longer people stay at a company, the higher the odds that they would become what the company wanted. I realized I didn’t want that to happen to me.
In a 10‑year period, I worked for five companies and spent two years in grad school. I moved from job to job, convinced the next stop was always the final stop.
My restlessness was easy to hide because my path was filled with impressive names and achievements, and when you’re on such a path, no one asks “Why are you doing this?” It took me a while to recognize this blind spot and have the courage to start asking myself those kinds of deeper questions in a serious way.
Which led me to walk away. Scratch that—run away. I even gave back a $24,000 signing bonus and missed out on a $30,000 bonus if I had been able to stick it out for another nine months. I left with the intention to become a freelance consultant, but soon enough, that story started to show its cracks as well. It didn’t take me long to realize I had been on a path that wasn’t mine, and to find a new way forward, I would need to step into the unknown.
About a year into this journey, I stumbled upon a phrase which helped me take a deep breath. It was the idea of a “pathless path,” something I found in David Whyte’s book The Three Marriages. To Whyte, a pathless path is a paradox: “We cannot even see it is there, and we do not recognize it.”1 To me, the pathless path was a mantra to reassure myself I would be okay. After spending the first 32 years of my life always having a plan, this kind of blind trust in the universe was new, scary, and exciting. Whyte says that when we first encounter the idea of a pathless path, “we are not meant to understand what it means.” 
To me, however, it meant everything.
The pathless path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It’s a call to adventure in a world that tells us to conform. For me, it’s also a gentle reminder to laugh when things feel out of control and trusting that an uncertain future is not a problem to be solved.
Ultimately, it’s a new story for thinking about finding a path in life.
As the world continues to change and technology reshapes our lives, the stories we use to navigate life become outdated and come up short. People are starting to feel the disconnect between what we’ve been told about how the world works and what they experience. You work hard, but get laid off anyway. You have the perfect life on paper, but no time to enjoy it. You retire with millions in the bank, but no idea what to do with your time.
The pathless path has been my way to release myself from the achievement narrative that I had been unconsciously following. I was able to shift away from a life built on getting ahead and toward one focused on coming alive. I was able to grapple with the hard questions of life, the ones we try so hard to ignore. And I was able to keep moving when I realized that the hardest questions often don’t have answers.
One of the biggest things the pathless path did for me was to help me reimagine my relationship with work. When I left my job, I had a narrow view of work and wanted to escape. On the pathless path, my conception expanded, and I was able to see the truth: that most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them. It is only when we cling to the logic of the default path that we fail to see the possibilities for making that happen.
I had been following a formula for life that was supposed to guarantee happiness. It didn’t. Confusion kept me on a path that wasn’t mine for more than ten years. Along the way, I learned how to play the game of success and achievement, but never paused to find out what I really wanted. I found myself in rooms surrounded by business leaders and didn’t quite fit in. I was in the wrong rooms, asking the wrong questions about how to live.


1. David Whyte, The Three Marriages: Reimagining Work, Self and Relationship (reprint; New York: Riverhead Books, 2010).

目錄列表