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The Pathless Path: An exploration of freedom, creativity & uncertainty in life off the default path

Almost four years ago I left a high-paying job in New York to become a freelance consultant. I thought this would be a simple case of swapping one labor for another but I was wrong.

Instead, I entered a new reality and had to grapple with many different questions:

  • 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 you life around work?

This e-book will be a collection of essays from Paul, perspectives on the modern state of work and some potential ways to think about navigating the new world of work, designing your life, and managing uncertainty while on a "pathless path."


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 these 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.  This kick started a now eight-year journey of grappling with the deep questions of life.

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.


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 that were 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 change my life.

Those people keep telling me "please keep going."

So here we are.


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 a 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


    The goal is for this to be launched sometime in March 2021. I'm pre-selling this to help nudge me towards completion?


    I will likely launch a version 1.0 in March and then create a revision that could possibly be printed in hardcover and paperback form for people that prefer this version.  I will need to explore more as things evolve.


    1. Introduction ("The Pathless Path," "World-Class Hoop Jumper," "Find a conversation bigger than yourself")

    2. Accidental Meaning & The Workism Crisis ("Accidental meaning," "Work myths," "overcoming traditionalism," "Why meaningful work is a lie")

    3. Beyond all-or-nothing leaps ("WTF?! Moments," "Prototyping life changes," "Learning internships," & "You can always go back")

    4. Getting lost on the "pathless path" ("How do you live if there is no payoff?" "Don't buy the culture." "Will people still love me?")

    5. Creating your own work without burning out ("I'm not a creative person and other lies," "Hacking Prestige," "What if people laugh? They Might" "Find the work you really want to keep doing," "Hustle Traps")

    6. Designing your life (the only option left) ("Your work or your life," "Figuring out what matters," "What if no one would laugh?")


    Many of these idea come from conversations and I love hearing what questions people have or what they want me to write about.  If you want to help proofread early sections and give feedback let me know and I'll give you free copies for you and some friends.

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    On September 30th, 12PM EDT


    The Pathless Path: An exploration of freedom, creativity & uncertainty in life off the default path

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      Thank you so much for purchasing! I'm a bit terrified of this bold leap in my aspirations but am excited to connect with you and other readers throughout this process. Please let me know if you have any questions or other comments. Thanks!

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