The Pathless Path: Imagining a New Story For Work and Life (The Pathless Path Collection Book 1)

by Paul Millerd

The pathless path has been my way to release myself from the achievement narrative that I had been unconsciously following. I was able to shift away from a life built on getting ahead and towards one focused on coming alive. I was able to grapple with the hard questions of life, the ones we try so hard to ignore. And I was able to keep moving when I realized that the hardest questions often don’t have answers. One of the biggest things the pathless path did for me was to help me reimagine my relationship with work. When I left my job, I had a narrow view of work and wanted to escape. On the pathless path, my conception expanded, and I was able to see the truth: that most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them. It is only when we cling to the logic of the default path that we fail to see the possibilities for making that happen.

Zen philosopher Alan Watts argued that “the desire for security and the feeling of insecurity are the same thing,” and that “we look for this security by fortifying and enclosing ourselves in innumerable ways. We want the protection of being ‘exclusive’ and ‘special.’”13

With the introduction of a “calling,” Luther and then Calvin both wanted to undermine the authority of the Catholic Church to govern an individual’s relationship with God. Luther took issue with the Church’s system of “indulgences,” in which people paid the Church to absolve them of their sins. He thought individuals should be able to have their own relationship with God. Calvin paired Luther’s increase in individual freedom with the idea that everyone is predestined to serve God through a specific calling. Working hard in the area of one’s calling determines the status of a person’s relationship with God. In the 1940s, philosopher Erich Fromm summarized this transformation, saying, “in the Northern European countries, from the 16th century on, man developed an obsessional craving to work which had been lacking in a free man before that period.” 23 Following the Reformation, then, work as an end in itself was no longer a crazy idea. People traded one master, the Catholic Church, for another, their vocation. But along with greater freedom and self‑determination came the anxiety and insecurity of never really knowing if you were working hard enough or doing the right thing. The Church’s expectations had always provided a way to measure “goodness,” and for many, these benchmarks no longer applied.

Austin Kleon, a prolific creator and writer, says that “creative work runs on uncertainty; it runs on not knowing what you’re doing.”46

Many self‑employed people are surprised to find that once they no longer have to work for anyone else, they still have a manager in their head.

As I started to experiment with how I spent my time, Taggart’s question remained in my head. I was fascinated by his claim that we lived in a time of “total work,” a state of existence in which work is such a powerful force that almost everyone ends up identifying as a worker first and foremost. The idea of total work was inspired by the German philosopher Josef Pieper, who first wrote about it in his book Leisure, The Basis of Culture. Writing in Germany after World War II, Pieper was shocked at how people were eager to throw themselves into work without pausing to reflect on what kind of world they wanted to build. To Pieper, this was evidence that German society had abandoned a connection to a traditional form of leisure.

In my life as a full‑time employee, work was a Monday through Friday thing I tried to minimize. Now it didn’t matter when I worked on my projects. They were energizing and rarely left me drained. For a long time, I had thought that if I wanted to be happier with my work, I just needed a better job. Now I saw that I just wanted a different relationship with work, one that, at least for now, didn’t come with a paycheck.

For me, I was finding that the act of creation was the reward itself. The philosopher Erich Fromm has argued that “creative union,” or when “man unites himself with the world in the process of creation,” is a way to experience love.62 I would have thought this completely absurd if I had not felt the depths of my connection to the world in those months.

Many people dislike some parts of their jobs. But they stay in their jobs because their suffering is familiar. To change would be to trade the known for the unknown and change brings discomfort in hard to predict forms. So people avoid change and develop coping strategies. They learn to sidestep the manipulative manager, or like me, change jobs every couple of years, plan vacations, stay busy, and get drunk during the weekend.

It was not until I found the philosopher Agnes Callard’s idea of an aspirational journey that I started to be more comfortable not knowing where I was headed. Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.”

One of the ideas that Seth Godin is known for is his suggestion that people on unconventional paths seek to “find the others.” These are the people who give us inspiration that doing things differently is possible and who might even join us on our journey.

The secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours. — Amos Tversky

Belief clings, but faith lets go. – Alan Watts

Eleanor Roosevelt once argued that “when you adopt the standards and the values of someone else or a community… you surrender your own integrity. You become, to the extent of your surrender, less of a human being.”

Seth Godin argues that humans are wired “to become a member in good standing of the tribe” and on the default path this means we will tend to conform.113 On the pathless path, powered by digital communities, we can surround ourselves with people that inspire us and push us to improve in the ways we care about.

The problem is that our culture has engaged in a Faustian bargain, in which we trade our genius and artistry for apparent stability. – Seth Godin

While on the default path, I was always surrounded by people that cared more about money and it was easy to convince myself that I placed very little importance on money. When I quit my job, I realized my assessment was wrong. Though I had gone several months without a paycheck while sick, the months after leaving my job were a completely different experience. Money went from a background consideration to one of the most important things in my life. I was experiencing what psychologists call, “scarcity mindset.”

Do I still worry about money? Yes. But now I’m hyper‑aware of how my financial insecurities might distract me from efforts that will help me stay energized and motivated on this path. Instead of playing to not lose, I’m playing to win.

On the pathless path, the goal is not to find a job, make money, build a business, or achieve any other metric. It’s to actively and consciously search for the work that you want to keep doing.

While money is important on the pathless path, using it as a filter for finding the work worth doing, especially at first, is a mistake. More important is the realization that finding something worth doing indefinitely is more powerful and exciting than any type of security, comfort, stability, or respect a job might offer. Fighting for the opportunity to do this work is what matters, whether or not you make money from it in the short term.

A significant barrier to figuring out what we really want to do is the voice in our head that warns us to stop when we consider or start doing things that are not broadly seen as “normal.” Professor and author Brene Brown’s clarification of shame and guilt helped me understand what’s really going on when we struggle to pay attention to our intuitions and desires. She defines shame as “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging.” She believes that most people give too much power to this emotion when making life choices.”

Maria Popova, who writes the popular site The Marginalian (formerly Brain Pickings), spends her days reading old books and essays. She’s passionate about finding ideas, beauty, and wisdom in these texts and then connecting them in her own unique conversation with the world. Her reflections on the connection between critical thinking and hope in an interview with Krista Tippett on the On Being podcast helped me transform how I wanted to engage with the world. She argued, “critical thinking without hope is cynicism. But hope without critical thinking is naïveté.”

We are living in a time when it’s possible for more and more people to design a life in which they can thrive. Yet many look at that possibility and say, “no thanks,” because it means discomfort, uncertainty, and a higher risk of failure.

You must be a little crazy to go against the grain of what most people think. Yet we should remind ourselves that these “experiments in living” as John Stuart Mill called them, are vital to pushing culture forward.