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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 type of work identity for another.

I was wrong

Instead, I went down a rabbit hole of asking the questions that lurked below the surface.  The ones we know are there but might be scary to consider.  And even scarier to take the answers seriously....

  • 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?

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 promise it will be unlike anything you've read.  This will be a self-published book chock full of nerdy wisdom, questions, and contemplations that might change how you see your relationship with work.  It will not be a 300-page book filled with the same examples in every other pop non-fiction book.  It is a book that matters to me and I'm excited to share it with others.


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.  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 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.


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


    The goal is for this to be launched sometime towards the end of 2021. I completely underestimated how much care I wanted to put into this project and since I've found it so much fun, I want to take the time and care it deserves.


    I will likely launch version 1.0 at first 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: Reflections from 

    2. The Default Path: How I became a world-class hoop-jumped and got what I thought I wanted

    3. Work, Work, Work: How work became so central in our lives

    4. Awakening: Opening up to the deeper mysteries via the way of loss and way of wonder.

    5. Walking Away: The reality of leaving a path that makes sense and the myth of the "leap"

    6. First Steps: The weirdness of taking the first steps in a new direction

    7. Making A Change: Dreaming bigger, dancing with fears & stepping into the unknown

    8. The Pathless Path: Embracing the unknown and seeing where it takes me

    9. The Secret: Discovering the secret of work

    10. The Real Future of Work: New stories for a new world


    Many of these ideas 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.

    -Quantity 1+
    On October 31st, 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!

      Good news! Since you already have a Gumroad account, it's also been added to your library.

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