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

by Paul Millerd

Growing up, I thought making $100,000 a year made someone rich. When I made that amount for the first time at 27, I felt like I had more than I could ever need. Yet I opted into an identity that didn’t accept such complacency.

We like to think that once we “make it” we can finally be ourselves, but based on who the companies selected, it was clear that the longer people stay at a company, the higher odds that they would become what the company wanted. I realized I didn’t want that to happen to me.

The pathless path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It’s a call to adventure in a world that tells us to conform.

an uncertain future is not a problem to be solved.

You work hard, but get laid off anyway. You have the perfect life on paper, but no time to enjoy it. You retire with millions in the bank, but no idea what to do with your time.

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.

The term “hoop‑jumper” was coined by writer and former professor William Deresiewicz to describe the behavior of his students at Yale, who seemed more concerned about getting A’s and adding bullet points to their resumes than using their time at one of the world’s best universities to follow their curiosity.7

internalizing the idea that education is “doing your homework, getting the answers, acing the test.” I had not developed a sense that “something larger is at stake” as Deresiewicz says, and only was playing the game of student, not using my mind. 9

world.” I had no wisdom to draw upon for navigating this important phase in life other than what everyone around me was doing: picking a path.

he was attracted to the law profession because “the steps are laid out for you.” A career in the law signaled to others that he “was a serious and intelligent person.” But the longer he spent on the path, he realized that the real promise had been that “life’s existential fears are traded for certainty.”11

prestige is “a powerful magnet that warps even your beliefs about what you enjoy.”

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 This was exactly what I was looking for.

“…in all men’s lives at certain periods…one of the most dominant elements is the desire to be inside the local Ring and the terror of being left outside.”

People were impressed by the job I was taking at GE, and I liked how the attention made me feel. I felt smart.

Out of all the jobs I could get from my school, this was one of the best and the magnet of prestige convinced me that was what I wanted.

“a first-person work‑centric story of progress about an individual’s life course.”15 From this perspective, my career was not a series of jobs, but a high‑stakes proposition, one where falling behind felt like failure. My colleagues and I dealt with this pressure by constantly talking about potential career paths and “exit options.” This was helpful for someone new to this world like me. I could figure out how to stay in the inner ring by following the wisdom of my peers.

This is the trap of prestigious career paths. Instead of thinking about what you want to do with your life, you default to the options most admired by your peers.

”unless you take measures to prevent it, this desire is going to be one of the chief motives of your life, from the first day on which you enter your profession until the day when you are too old to care.” He believed “any other kind of life, if you lead it, will be the result of conscious and continuous effort.”

The philosopher Andrew Taggart believes that crisis moments lead to “existential openings” that force us to grapple with the deepest questions about life.16 He argues there are two typical ways this happens. One is the “way of loss,” when things that matter are taken from us, such as loved ones, our health, or a job.

Those few days were filled with tears and overwhelming emotion, but also with beauty and a profound sense of meaning. The proof of his life’s work was in front of us. He had succeeded in creating a world better than the one he had grown up in. It was clear to me in those moments that family, love, and relationships were the most important things in the world.

In those months, everything was filled with meaning. Relationships felt more important. Books, songs, and movies made me cry, and I became more curious about everything.

but after three years of putting my career first, I was able to put life first. My memories of business school are the conversations with friends at Beacon Hill Pub, watching Jersey Shore at Mike’s, cultural celebrations, formal parties, intramural hockey, and basketball games, touring factories across the world, and most notably, performing an Irish Jig in front of 500 people. In a class at the end of the two years, my friend Kurtis shared that he thought I was someone that “lived life to its fullest.”

In addition to normal consulting projects, we recruited and staffed these consultants on short‑term projects. These people, self-described “independent consultants,” were fascinating. Everyone had a unique story and way of working. Some worked three days per week. Others worked for six months and then took six months off to travel.

This was the first time I had direct contact with anyone who did anything other than work full‑time. I was intrigued.

This is the hardest thing about being sick. It isn’t like a breakup when people tell you it will get better and you know they’re right. When you’re sick, you have to believe you will get better even though your body is telling you you’re crazy to think that.

While I was sick, I had contemplated the question, “what would people think if I couldn’t work again?” and had been surprised by my answer. I would be okay.

people who face crises often experience “post-traumatic growth” and that this manifests as an “appreciation for life in general, more meaningful interpersonal relationships, an increased sense of personal strength, changed priorities, and a richer existential and spiritual life.”

If we are going to imagine a new way forward for our work and our lives, we need to understand where our current ideas from work come from and how they have changed.

German historian Max Weber found that the “spirit of capitalism” struggled to take hold in societies that embraced a “traditionalist” mindset towards work.18 In Weber’s view, a “traditionalist” view of work is one where people work as much as they need to maintain their current lifestyle, and once that aim is achieved, they stop working.

The idea that people might decide to work less is hard for some people to imagine. This person, a foreigner, likely grew up in a culture like mine where working in a formal job continuously throughout adulthood is what most people do.

The difference between working to meet one’s needs versus meeting expectations raises a question.

It might surprise you that in Greece, during the time of Aristotle more than 2,000 years ago, work was simply considered a necessary evil. The prime aim of life...

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 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.

Religious scholars point out that the Protestant “work ethic” is more than a blind obsession with work. It is paired with thrift, self-discipline, and humility. Yet as fewer people look to religion for wisdom on how to navigate life, they are only left with the watered‑down version of these views.

In Anne Helen Peterson’s widely read essay “How Millennials Became the Burnout Generation,”

Adults talked about work all the time and constantly asked me what I wanted to do when I grew up.

The educated, hardworking masses are still doing what they’re told, but they’re no longer getting what they deserve.

The modern version of the default path was born after World War II, in a period of unprecedented economic growth. This shift in thinking was led by the United States

This economy generated full‑time jobs with good incomes, benefits, and career opportunities, enabling a broad middle class to reach new levels of wealth and material comfort.

No longer was it even acceptable that the child should be like his parents and live as they did; he must be better, live better, know more, dress more richly, and if possible, change from father’s trade to a profession. This dream became touchingly national.28

“Since tracked careers worked for them [the baby boomers], they can’t imagine that they won’t work for their kids, too.”

his generation’s mistake was to assume that the paths that worked for them would work forever:

During that stretch of time, it would have been a mistake to opt-out of the default path because as Thiel points out, “whether you were born in 1945 or 1950 or 1955, things got better every year for the first 18 years of your life, and it had nothing to do with you.”

We entered adulthood thinking we could copy‑and‑paste what our parents had done, but it was more complicated than that.

That you didn’t simply work to live, but that it should be one of the most important things in your life.

We didn’t want to see work merely as an obligation, we also wanted it to be meaningful and fulfilling. We wanted the modern version of the “calling” that Oprah talked about.

In the 2010s the expectation that work should be meaningful became a default expectation of college graduates. Young people no longer wanted simply to bide their time at a job but wanted a job with passion, purpose, and fun. By 2019, a survey of workers in the United States and Canada found that more than offering good pay and benefits, 78% of people thought “employers have a responsibility to keep employees mentally and physically well.”

Their research found that instead of joy, meaningful experiences were “associated with mixed, uncomfortable, or even painful thoughts and feelings, not just a sense of unalloyed joy and happiness.”36 Despite thinking I wanted fun and joy at work for most of my career, when I reflect on the most meaningful moments of my career, they involve overcoming obstacles, or getting through setbacks to complete something I didn’t think I could.

Sociologist André Gorz spent the latter half of the 20th century writing about the role of work in society. He argued that many countries had evolved into places where the primary way one gained “membership” in society was through formal work. He called these places “wage-based societies” where the central ethic was, “never mind what work you do, what counts is having a job.“