The Pathless Path: Imagining a New Story for Work and Life

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 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.

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