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

by Paul Millerd

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. For me, it’s also a gentle reminder to laugh when things feel out of control and trusting that an uncertain future is not a problem to be solved.

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.

I wanted him to see the potential I saw. Yet in my own life, I was doing the same thing. With every new job, I convinced myself I was thriving. But what I was really doing was trying to escape feeling stuck.

What I really wanted was to be part of the “inner ring,” which C.S. Lewis famously detailed in a lecture given at King’s College in 1944. He argued, “…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.”

Part of me had been secretly excited about quitting my job and moving to a new city without a job, drawn by the possibilities of adventure. That part of me would get its chance but it would have to wait several years.

A year went by and I decided my next step was going to a top business school. This idea did not emerge out of thin air. Talks of applications, essays, and school rankings filled the daily lunchroom conversations. These people were my friends and when they were accepted into elite business schools like Harvard and Stanford, it seemed obvious that I should do the same thing.

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.

In describing the power of the inner ring, C.S. Lewis warns that, ”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 o...

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. The other path is the “way of wonderment,” when we are faced with moments of undeniable awe and inspiration.

What was I living for? What did I really want? How did I want to look back on my life when it was my time to go?

I made it through the week and that weekend I called Peter, the head of our office, and told him everything. He clearly understood how scared I was because when I proposed taking a week off or working remotely, he suggested I take a month off, paid, to focus on recovery. I was worried about letting him and the client down, but he told me that those things were trivial. At the time, our firm was struggling and as the head of the office, he put his own job at stake by pausing an important client project. It was a moment of leadership that inspired me.

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. So much of my identity had been connected with being a high achiever. Straight A’s. Dean’s List. McKinsey. MIT. When I was sick, I would have traded every last credential for a single day of feeling okay.

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.

In “Jobs, Careers, and Callings,” a famous study by Yale professor Amy Wrzesniewski and others, people were asked if they defined their work as a job, career, or a calling. People who defined their work as a calling saw their work as “inseparable from their life” and worked, “not for financial gain or career advancement, but instead for the fulfillment that doing the work brings to the individual.” The researchers boldly concluded that if people could find work they saw as a calling it would improve their “life, health, and job satisfaction.”32

When he got raises or promotions the discomfort would subside but never disappear. Slowly, he became more curious about that feeling and realized that despite his external success, he had become a “passive participant” in his life. Eventually, this convinced him to embark on his own pathless path.

My final list included four items: health, relationships, fun & creativity, and career. Since 2013, this list pops up on my phone at 8:30 a.m. each morning. Staring at those four items, in that order, was scary. Without knowing it, I had embraced a question that would shape my decisions: “How do you design a life that doesn’t put work first?” The answer, my dear reader, is simple. You start underachieving at work.

Why was I trying to get a raise when I knew I was not in a good environment? What was I seeking? Why did I keep changing jobs every two years? What was that pebble in my shoe really telling me?

I defined a leader broadly as someone that could be a “role model in all aspects of their life.” I specifically listed nine principles, a collection of phrases, quotes, ideas, and beliefs that I hoped to embody throughout my career. Some examples included a desire to lead with empathy, to embrace humility, to inject humor wherever possible, to avoid becoming too serious, to prioritize learning, to think independently, and to create memorable experiences for others through my work.

I couldn’t be burnt out. I was too smart! Burnout is for investment bankers and lawyers working every weekend and logging 80‑hour weeks. I tried to explain it away but I couldn’t.

Are you a worker? If you are not a worker, then who are you? Given who you are, what life is sufficient?

Unfortunately, the pathless path is an aspirational path and can never be fully explained, as Callard tells us, so attempts to convince people that you are moving in the right direction can be futile. People who value comfort and security often cannot understand why anyone would willingly pursue a path that increases discomfort and uncertainty.

It’s a cliché to say that we find things exactly when we least expect them, but that’s exactly what happened to me. For years I had wanted to find someone to be able to “settle down” with. But I was looking for someone within the context of the default path, a script of how life should be rather than what I really wanted. I now agree with Joseph Campbell, who through his study of the human experience through our ancestors’ stories, concluded that “We must let go of the life we have planned, so as to accept the one that is waiting for us.”

No underlying logic justified my spending and a lot of it could be classified under what writer Thomas J. Bevan calls a “misery tax.” This is the spending an unhappy worker allocates to things that “keep you going and keep you functioning in the job.”96 For me, it was a mixture of alcohol, expensive food, and vacations, and as the amount inched up during my career, I started to believe that my spending was the reason I was working.

The pathless path is a define-your-own-success adventure. In the first couple years, it felt silly to tell people how I defined success: feeling alive, helping people, and meeting my needs. Over time, I realized that the real benefit of this orientation towards success was that I wasn’t competing with anyone. This meant that the odds of success were incredibly high and the benefits of staying on the pathless path would only compound and increase over time.

The world is changing and the pathless path is just one way to exit the world of bad tests. As more and more people decide that these tests are silly, we can create new and better games. Ones that aren’t optimized for how employers like to see the world, but rather align with how we are motivated to learn and grow through our lives. I think this really matters and I agree with Graham’s assessment: “This is not just a lesson for individuals to unlearn, but one for society to unlearn, and we’ll be amazed at the energy that’s liberated when we do.”

“Not till we are lost, in other words, not till we have lost the world, do we begin to find ourselves, and realize where we are and the infinite extent of our relations.”

Enough is knowing that no amount in my bank account will ever satisfy my deepest fears. It’s knowing that I have enough friends that would gladly open their door and share a meal if I was ever in need. It’s the feeling that I’ve been able to spend my time over an extended stretch of time working on projects that are meaningful to me, helping people with a spirit of generosity, and having enough space and time in my life to stay energized to keep doing this over the long‑term. Enough is seeing a clear opportunity that will increase my earnings in the short‑term, but knowing that saying “no” will open me up to things that might be even more valuable in ways that are hard to understand. Enough is knowing that the clothes, fancy meal, or latest gadget will not make me happier, but also that buying such things won’t mean I’m going to end up broke. Enough is having meaningful conversations with people that inspire me, people that I love, or people that support me.

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

Introspection means talking to yourself, and one of the best ways of talking to yourself is by talking to another person. One other person you can trust, one other person to whom you can unfold your soul. One other person you feel safe enough with to allow you to acknowledge things—to acknowledge things to yourself—that you otherwise can’t. Doubts you aren’t supposed to have, questions you aren’t supposed to ask. Feelings or opinions that would get you laughed at by the group or reprimanded by the authorities.132

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. This is one of the most important secrets of the pathless path. With this approach, it doesn’t make sense to chase any financial opportunity if you can’t be sure that you will like the work. What does make sense is experimenting with different kinds of work, and once you find something worth doing, working backward to build a life around being able to keep doing it.

This book you are reading did not require anyone’s permission to be published. I just decided to do it. I wrote it myself, hired editors and designers to help me, and put my name on it as the publisher. You can do this too.

Thinking we have to serve a mass audience is default path thinking. An industrial, “bigger is better” mindset assumes that everyone is competing in a mass market. In the digital world, it’s easy to envision that this mass market is the only competition for the same audiences and attention. However, even if my podcast might sit right next to NPR’s This American Life in the podcast app, what I am doing is completely different.

Figuring out who you want to serve is an important element of the pathless path. On the default path, your job often provides recognition and praise. When you are on your own, without a specific job or colleagues, you may miss that kind of support. This is why it’s so important to know what kind of people you want to work with and who you want to serve. Finding the right people, those who might offer support and encouragement along the way can have an outsized effect on your confidence and courage to keep going. I have benefited from this sort of kindness on my journey, especially early on from my aunt Debbie, Noel, Cam, Jordan, and many others. Tyler Cowen has argued that one of “the most valuable things you can do with your time and with your life” is to believe in people.144 Being a recipient of this encouragement has inspired me to create a rule for myself: any time I consume something from an individual that inspires me, I have to send them a note to let them know. Creating and sharing in public takes an incredible amount of courage and I remember how awkward and scared I was at the beginning of my journey. It’s easy to tell people what they got wrong but much harder to say “I love what you are doing. I hope you keep going and let me know if I can help.”

The biggest challenge to creating your virtuous cycle and one of the most dangerous failure modes of the pathless path is cynicism. Many people who leave the default path do so because they’ve become cynical and are driven by a desire to escape. But escaping is only the first step of leaving a certain path behind. In order to create a sustainable journey and path, it requires finding ways of orienting to the world that leave space for hope. At the beginning of my journey, I wanted to prove people wrong and that my way of living life was good and right. My writing was cynical because I couldn’t express why I cared about those ideas. I was depending more on facts than the songs singing in my soul. When I was brave enough to open my heart, I got more support and that led not only to a better path but a more exciting future.

I encourage everyone to write a description of the person you don’t want to be, then brainstorm actions that might create that outcome. This exercise may be uncomfortable because undoubtedly you will see traces of the person you imagine in your present life. These traces are clues about what to change in your life right now.

In the paycheck world, there used to be a saying: dress for the job you want, not the job you have. The analogous idea in the free agent world is: learn to exercise the freedoms you might acquire, not just the freedoms you have. – Venkatesh Rao

In one significant quote, Morrie reflects on the difference between living and dying: “Dying,” Morrie suddenly said, “is only one thing to be sad over, Mitch. Living unhappily is something else. So many of the people who come to visit me are unhappy.” Why? “Well, for one thing, the culture we have does not make people feel good about themselves. We’re teaching the wrong things. And you have to be strong enough to say if the culture doesn’t work, don’t buy it. Create your own.”

During the Covid‑19 pandemic, many people around the world were forced to work remotely. Suddenly what I had been writing about for years became poignant for many people. Sitting at home, knocked out of their daily rhythms, people confessed to me that they were shocked at how much of their identity was wrapped up in work and how lost they had become in their own lives. They wanted to find a new way forward.

Second, reflect. When I started reflecting on my true self, I was able to start building a life around the things I valued. Most of us run on autopilot through life but we can break out of this mode by considering even the simplest reflection exercises.

Go and see what might happen if you dare to seek out, as the Poet Mary Oliver has called your “one wild and precious life.”