Over the past two and half years I’ve been navigating unknown territory, grappling with the deep philosophical questions of how to live life and wondering how my parents generation, the boomers, lived life as if they had a map.

For most of my life, I pretended I had a map. It seemed that was what you were supposed to do as an adult. In job interviews I lied about my career path and intentions to stay at that company. In my grad school interview I outlined a very specific plan that also happened to align with the goals of the program. The scary things is that I had almost started to believe my map was right.

Before I left my full-time job in 2017, I had the sense that things were going to be okay. That there was a plan. That life made sense.

Self-Employment Opened My Eyes & Made Me Curious

The truth was I had no idea and it took taking the leap to self-employment to open my eyes. Here is what I wrote a year into it:

A career is an artificial path which you must always manage, have a story for and be networking so that you can take the next step. The next step being up, of course.



Being self-employed, there are no promotions or paths to judge yourself against. Other people’s confusion with this fact comes out when people invariably ask “what’s your plan?” or “how’s business doing?”

While this question has no answer, I respond with what I know to be true: “I am following my creative energy and seeing where it takes me.” This tends to drive a lot of people who are deep into career thinking a bit mad.

As I’ve spoken to hundreds of people that have been carving their own paths and researched how people navigate life and stay sane along the way, a new kind of map has emerged. Not one that gives a perfect sense of certainty or comfort, but one that helps give language to feelings that are hard to name.

I underestimated the transition to self-employment. I imagined a smooth transition from executing on consulting projects for a company to doing the same on my own as a freelancer with a bit more flexibility.

Instead, I found myself staring face to face with uncertainties and questions. 

What is the proper way to navigate life?

Should certainty be a goal?

What is the best way to live life?

Is there a best way?

Why was I so sure that self-employment was just about making money?

How much money did I want to try to make?

A Map For Navigating The Pathless Path

Is this the map we are looking for?

As I’ve explored what it means to be self-employed I’ve realized that many people progress through a series of four phases. These phases can last months or they can last years. In my case I remained restless for almost ten years. It took another couple of years for my imagination to be ignited in a way where I had the courage to take my first steps and now I’m committed to the journey and I’m not sure how long that will last until I decide to blow it up and head in a new direction…

#1 Restlessness

“it is a cry for something else, often the physical body’s simple need for rest, for contemplation, and for a kind of forgotten courage, one difficult to hear, demanding not a raise, but another life.”  — David Whyte

Khe Hy described this feeling of restlessness as a “pebble in his shoe” that he couldn’t remove. Many others describe it as a feeling of “low grade anxiety” that they cannot shake. 

Others come face to face with their own restlessness in recovering from a crisis or major life transition. Losing a job, facing a health crisis, losing a loved one or even having a child can inspire people to start looking for a new train of thought.

For David Vaucher, it was losing his father before his dad was able to fulfill his dream to retire in France:

“Before he died, my plan was working: I was making more money and getting ready to buy bigger things.

After he died, the sustained growth in income was dwarfed by the growing fear that if I didn’t take action somehow, I was headed down the same path”

For me, I kept changing jobs every 18 months convinced I would shake this restlessness. 

I realized what many others do — that I had to dream in a new direction.

#2 Imagination

When we see other people do things like quit their jobs, move across the world or make a career change, we see it as a dramatic leap.

In reality, what you are missing is how that person’s imagination and view of the world has been evolving over the past several months and years. This is often a slow shift that happens from meeting different kinds of people, reading a book or being forced to adapt to a situation within a certain set of constraints.

Five years before I took the leap to self-employment, I was doing work with a number of freelance consultants. I got to know many of them and found they were incredibly energized, happy and able to support their life. I remember being full aware of this and it planted a seed in my brain that there were different models for how I might live and work later in my life. 

It took five more years before I took my “first steps,” but knowing that adults existed who enjoyed life and played by different rules gave me permission to investigate alternative paths in the world through books, podcasts and conversations.

A friend, Lydia Lee, talked about a trip she took to Malaysia in which she met a digital nomad who was running a marketing firm from his laptop:

“being able to meet him in real life…made me realize I could work from my laptop”

This seems to trivial, yet to her journey it was profound. Meeting this person made something impossible real. Even though it would be another six months before she decided to quit her job, it sent her back home with a new thought. That there could be a different way.

#3 First Steps

“As we have shown in this research, a person focused on her ideal self is more likely to lose sleep over her “wouldas” and “couldas” than her “shouldas.”’ — Gilovich & Davidai

In a recent paper titled “The Ideal Road Not Taken”, Professors Gilovich and Davidai tried to understand what people regret. What they discovered is that regret was linked to two different conceptions of a self. 

The first is an aspirational self, which is a version of ourselves that we aspire to. The second is an “ought to” self. This is the self that has to do with responsibility. We “ought to” take care our our family, go to work, and so on.

The thing they found was that when people fail to live up to their “ought to” self, they quickly took action to fix it and were much less likely to regret their actions. When someone failed to match their apirational ideas, however, they experienced a much higher degree of regret.

My belief is that many people who take some kind of leap are able to intuitively make this calculation. We could even call this the Gretchen Rubin Principle because of how clearly she articulates the implications in her interview with Tim Ferriss:

“I’ve come to a point where I’d rather fail as a writer than succeed as a lawyer, and I need to try and fail or try and succeed, but I need to do it.” — Gretchen Rubin

Finally “taking the leap” often comes with confusing emotions. Here are how some people described the leap:

“Seeking and questioning”

“Terrified but also excited”


“You have to make this work”

There is a duality of emotion — the acceptance that they finally took the enormous weight and fear of regret — of not having tried — and entered new territory. 

Now with the pressure to make it work.

#4 Commitment

“…that the moment one definitely commits oneself then Providence moves toe. All sorts of things occur to help one that would never otherwise have occurred” — WH Murray

The first few months of carving one’s path can be disorienting. Many, like me, find that the worries they expected are not the worries that actually matter. Many find that the money issues are less stressful, while some want to run back to their salary.

In the first six months of self-employment, I was 100% focused on “making it” as a freelance consultant. After landing three clients in month 5 and proving to myself that I could support myself this way, there was a sense of relief.

I decided to take the next two months off and see what happened. I had a bunch of ideas in my mind. During this time, I ended up launching a blog, a podcast, and future of work mindset tool — all of which are still central to my work to this day.

During that time I also laughed to myself because I knew I was at the very beginning. I had graduated from the 1-year of permission I gave myself to experiment when I left my job and moved on to a longer journey without an end date. I wasn’t sure of the destination, but I knew I was committed to keeping the journey going.

Embracing A “New Train Of Thought”

“…It can be a release then, to think, that when we first come across the idea of a pathless path, by definition, we are not meant to understand what it means” — David Whyte

I believe that many of us have a secret urge to blow it up and “make it on our own.” I also believe that because most people are looking for a map to navigate that transition, few people tend to move past the imagination phase.

While these four phases are not a “playbook,” they offer a loose set of phases that many resonate with how creators, entrepreneurs and solopreneurs navigate carving their own paths. 

If you look at the most creative people in the world, you often see kicking off a new journey every year or two. 

Grant Achatz is one of these creators. He is the head chef at Alinea, one of the top restaurants in the world. When he reached that status, what what did he decide to do next?

He decided to start over:

“We are ripping apart a restaurant that is working incredibly well. It’s the busiest its ever been. Why fix something that is not broken? Well because if we wholeheartedly gonna uphold that philosophy that we started ten years ago…the beginning of a new train of thought” 

— Grant Achatz, Founder of Alinea

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