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

by Paul Millerd

It’s a state familiar to many. Study hard, get good grades, get a good job. Then put your head down and keep going, indefinitely. This is what I call the “default path.”

It didn’t take me long to realize I had been on a path that wasn’t mine and to find a new way forward, I would need to step into the unknown.

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.

As the world continues to change and technology reshapes our lives, the stories we use to navigate life become outdated and come up short. People are starting to feel the disconnect between what we’ve been told about how the world works and what they experience. 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.

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.

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 had been following a formula for life that was supposed to guarantee happiness. It didn’t. Confusion kept me on a path that wasn’t mine for more than ten years. Along the way, I learned how to play the game of success and achievement, but never paused to find out what I really wanted. I found myself in rooms surrounded by business leaders and didn’t quite fit in. I was in the wrong rooms, asking the wrong questions about how to live.

For most of my life, I’ve had the gift of seeing the greatness in others. It hurts when I see people stuck or unable to pursue their dreams, and I want to do anything I can to help them.

writer Leo Rosten once argued was the purpose of life: “to be useful, to be honorable, to be compassionate, to have it make some difference that you have lived and lived well.”

a hoop-jumper just like Deresiewicz’s students at Yale, 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.

shared that 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.”

prestige can be thought of as the attention you get when you do things that others see as impressive. Paul Graham, the founder of a startup incubator and mentor to thousands of young people, sees this attention as a trap. In his view, prestige is “a powerful magnet that warps even your beliefs about what you enjoy.”

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.

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 of life, if you lead it, will be the result of conscious and continuous effort.”

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.

Professors Richard Tedeschi and Lawrence Calhoun have suggested that many 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.

Contemplating one’s place in the universe was seen as one of the most worthwhile things to do and at minimum, more important than the “money-making life,” which Aristotle described as “something quite contrary to nature…for it is merely useful as a means to something else.”

People should be expected to work, but the reason is to meet the needs of our families and communities.

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.”

When I tried to talk about the incredible amount of time I was wasting on this project, people quickly redirected my inquiry, saying, “It may suck, but you’re getting something to put on your resume!” or “Everyone has to work, what are you supposed to do?” or “You should be grateful for being paid.” No one wanted to grapple with this fundamental question: “Why the hell are so many grown adults spending their time on obviously pointless tasks?”

The notion of spending the rest of my life doing mindless busywork horrified me and motivated me to keep searching for better options.

he walked away to find a new path. However, it took him a long time to make that decision. He reflected, “It definitely wasn’t a sudden realization. It’s a little bit like having a pebble in your shoe, where you’re walking and something is off, and it’s mildly uncomfortable.”

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.

I was physically present but detached. Rather than participating in meetings as a good team member, I observed them as a visiting anthropologist. I saw my colleagues with new eyes. Are they happy? What kind of pain or challenges are they dealing with? Is this how they want to be spending their time? Once you ask these questions there is no going back. Not because of the contradictions in other people’s lives, but because it makes it difficult to live in contradiction in your own life.

says that “creative work runs on uncertainty; it runs on not knowing what you’re doing.”46 The creative work of finding a new life path is similar.

My biggest barrier was my inability to imagine an alternative life. My creative experiments were exciting, but they didn’t suggest an obvious next step. It was easier to aim toward another raise or promotion than daring to ask myself deeper questions.

Your life is too short and too valuable to fritter away in work. If you don’t get out now, you may end up like the frog that is placed in a pot of fresh water on the stove. As the temperature is gradually increased, the frog feels restless and uncomfortable, but not uncomfortable enough to jump out. Without being aware that a chance is taking place, he is gradually lulled into unconsciousness. Much the same thing happens when you take a person and put him in a job which he does not like. He gets irritable in his groove. His duties soon become a monotonous routine that slowly dulls his senses. As I walk into offices, through factories and stores, I often find myself looking into the expressionless faces of people going through mechanical motions. They are people whose minds are stunned and slowly dying.

getting rejected from jobs repeatedly, never finding the right fit, facing health challenges and hard questions were all events that sent me in an inevitable direction that was only obvious upon reflection.

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.

We can explain this strategy with a simple equation: Uncertain Discomfort < Certain Discomfort + Coping Mechanism

In other words, given sufficient coping strategies, people will be willing to tolerate consistent levels of misery for long stretches of time. Is there anything that can override this? In my conversations with people who have made changes in their life, one thing seems to work reliably: wonder.

In thoughts about the future, worry is traded for wonder. People stop thinking about worst‑case scenarios and begin to imagine the benefits of following an uncertain path. They get curious about who they might become if they embrace discomfort and are filled with a sense of urgency that says, “if I don’t do this now, I might regret it.”

“Who I was before and after was best defined as I was uncertain before the trip and I was confident after the trip in terms of what the potential for life was.”

call our “‘ought to’ self.” This is the voice that helps us follow through on commitments but can also keep us from making changes in our lives. This is the voice that might convince you that leaving a job is an abdication of responsibility. We “ought to” keep working. This impulse is helpful most of the time, but compounded over one’s life it stops us from moving towards what Gilovich and Davidai call our “ideal self.” When people reflect on their lives, these are the things that people regret most – not moving towards their ideal selves.

Making life changes requires overcoming the discomfort of not knowing what will happen. Facing uncertainty, we make long mental lists of things that might go wrong and use these as the reasons why we must stay on our current path. Learning to have a healthy distrust of this impulse and knowing that even if things go wrong, we might discover things worth finding can help us open ourselves up to the potential for wonderful things to happen.

where people like Seth Godin, Derek Sivers, and Tim Ferriss exposed me to a broader set of ideas of how to live and work.

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.

I suggest people take a more active approach to find what I call “path experts.” These are people ahead of you on a path you might be interested in taking. It could be someone who left a job like yours or someone exploring a way of living that fascinates you.

When you meet others on a similar path, there is an instant bond and a deep sense of knowing about the challenges you are both going through. You can smile in a way that says, ”I know, I know,” skip the “what do you do?” question, and start a deeper conversation.

On the pathless path, people like this are essential. You might find them in your family like Chris, while traveling like Lydia, or at a conference like I did. These relationships offer a space where you don’t need to have good answers for what you are doing or what comes next.

On my previous path, there was a hidden cost to my success. The consistent financial rewards helped me live a smooth existence, needing to rely less on others the more I succeeded. In some circles, this is celebrated as the ultimate aim of life, but for me it led to a certain emptiness that I didn’t fully understand until I found myself on a path that forced me to find the others.

You can leave the default path before facing your fears, but the pathless path forces you to reckon with them no matter what.

Tim Ferriss’ “fear setting” reflection exercise helped me reframe them and see fear in a completely new way.74 The exercise has six steps. The first four are straightforward: Write down the change you are making. List the worst possible outcomes. Identify actions you could take to mitigate those outcomes. List some steps or actions you might take to get back to where you are today.

some fear‑related problems cannot be solved. The authors of Designing Your Life offer a helpful reframe, calling these issues “gravity problems” which are part of life “…but, like gravity, it’s not a problem that can be solved.”

In a blog post titled, “Five Regrets of The Dying,” one of the most viewed online posts, she shared her reflections. The most common regret? Not staying “true to themselves” in their lives and focusing too much on what others expected of them.

At the hotel, everyone started asking: Why was I moving to Taiwan? Wasn’t I worried about healthcare? Would I ever have a “real job” again? Didn’t I want a family at some point? Why was I doing this? What was my long‑term plan? I felt under attack and that I had disappointed the people that mattered most.

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.

This path offers profound personal growth, but its benefits often remain invisible to others. When you are on such a path, you are hyper‑aware of this disconnect, and this can cause a lot of distress.

the questions that raced through her mind at the time: “What will people think of me? I don’t even know what to think of me. Am I being completely irresponsible? Do my parents think I’m a failure? Are my friends as supportive as they seem, or do they think I’ve gone off the deep end?”