The Pathless Path: Imagining A New Story For Work and Life
How did work become the center of our lives?
This is the question that sent me on a five year journey to figure out if there was a better way to build a relationship to work.
The surprising answer? There was., but it meant rejecting much of what I thought was true growing up and also what most of the people around me believed.
I had quit my job with the idea that I would become a freelance consultant, working a bit less and having a little more flexibility. Really, I had no idea what I was doing. A few months into the journey, I felt pulled by a deep feeling that I needed to experiment much more with my life.
I started contemplating hard questions, the ones I had kept safely buried beneath the surface.
- How much money did I really need?
- Who was I if I didn't have a clearly legible title or path in life?
- How do you handle not knowing what the future looks like?
- What did I really want to work on?
- How do you design a life worth living?
- What happens when you don't orient your life around work?
Over the next few years, I attempt to answer these questions and to do so, I find myself drawn to living abroad, experimenting with non-work, unleashing my curiosity, and grappling with my insecurities and fears.
Surprisingly, I start to find some simple but powerful answers from history, philosophy, and my own experience, ones that offer a dramatically different story about our modern relationship to work.
WHO AM I?
I grew up in a small town in rural Connecticut surrounded by a big family. In college I became captivated by the prestigious world of strategy consulting and spent more than two years trying to break in, not knowing the codes or norms of this weird, elite world. I spent almost ten years in the industry including a short break for an MBA and generally liked the work.
Yet the whole time everything seemed off. It seemed as if work was the most important thing in everyone's life and for a while, I played along. After a health crisis at the age of 27, I started to realize that I didn't have any sort of identity beyond achievement-driven worker.
In 2017 I built up the courage to leave my job and have been trying to experiment with different ways of working and living life. During this time I discovered the idea of the "pathless path" which helped me to navigate the uncertainty and weirdness of following a path of self-employment. This book is a culmination of those reflections.
WHY DID I WRITE THIS BOOK?
In 2015 I challenged a friend to post an article publicly on LinkedIn. I promised to do the same. It was terrifying to hit that publish button. What would my colleagues say? Would my boss tell me I shouldn't be sharing my opinions in public?
No one said anything. So I kept posting.
Eventually, my writing attracted people curious about the same things. Making friends can be difficult in big cities but this seemed like a secret weapon.
Over the last five years, I've met hundreds of people in-person and online who have resonated with what I've written and it's changed my life.
Those people keep telling me "please keep going."
So here we are.
WHO WILL LIKE THIS BOOK?
People who will like this book include:
- People who enjoy the writing on my newsletter or blog
- Solopreneurs and creators who are grappling with the strange tension of being an illegible person in a reality designed around work
- People who are curious about the future of work and what it means for careers and our lives
- People who feel that their relationship with work is "off" and can't put their finger on why
- People who want to dream bigger about different ways of living their life
- People who have things they wish to express in the world that don't quite fit neatly in a job-focused package
Overview of the Book
Part 1: The Default Path
Exploring the history of work through my own aggressive pursuit of a prestigious and impressive career
1. Introduction: An exploration of the default path of success, what the pathless path really is about, and why it matters
2. Getting Ahead: My journey of learning how to become a "hoop-jumper," breaking into strategy consulting, going to business school, and then how dealing with the loss of my health and someone important changes what I value
3. Work, Work, Work: An exploration into the history of work and trying to make sense of our current relationship to work around the world and some of the fundamental flaws
4. Awakening: The start of a slow but steady drift towards a breaking point while I discover an inner creative and experimental energy that needs to be expressed
5. Breaking Free: Quitting my job and taking the dealing with the loss of an important identity
6. The First Steps: Learning how to prototype a life shift, opening up to possibility and wonder, finding the others, taming my fears and deepest insecurities
Part 2: The Pathless Path
Embracing a different kind of journey, one focused on coming alive, embracing uncertainty, experimenting, and being open to possibility
7. Wisdom of The Pathless Path: Embracing non-doing, falling in love, taking extended breaks, leaning into leisure, re-thinking retirement, and money, and learning to trust the world
8. Redefine Success: How to shift away from the default modes of success and towards your own definition, designed around building your own tribe, defining enough, and shifting beyond scarcity mindset
9. The Real Work of Your Life: Engaging in the real work of your life: finding the things you want to keep doing. In addition, unleashing your inner creative spirit, figuring out how to be useful, and injecting hope into the journey
10. Playing The Long Game: How to sustain the journey by working backward from who you don't want to be, learning to reinvent yourself, embracing abundance, creating your own culture, and developing your own principles