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

by Paul Millerd

Rebecca Solnit supplies the words I didn’t have at the time: That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.

There’s a phrase in Chinese, “wu wei,” that describes how I felt. In English, its translation is “non-doing,” but not in the sense of doing nothing. Non-doing is not about escaping anything or being lazy but instead refers to a deep level of connectedness with the world.

I had stripped down my life to the bare minimum. I had few possessions, was releasing my grip on the future, and was opening myself up to the unknown. I spent these days shifting back and forth between the dizziness of feeling lost and the certainty that I was exactly where I was supposed to be.

I discovered someone else who was asking the deeper questions and was willing to embrace uncertainty over doing what was expected. In other words, I had found someone fully embracing their own pathless path.

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.”

For most of my life, I had paired the idea of doing nothing with laziness. Living in another country enabled me to see that this was a very American way of seeing the world.

he shared with me, “I used to think ‘this job isn’t so bad, I make enough money to make it worth it.’ Then you get a breath of freedom and realize, no, it may have been worth it at one point, but not anymore.”

When people have time, they try new activities, revisit old hobbies, explore childhood curiosities, and start volunteering and connecting with people in their community.

reflected that “new ideas often pop up and old topics of interest float back into my consciousness. I find myself writing notes and thinking more freely. This is the creative process, liberated by the neocortex now that the mind isn’t wholly occupied by the strain of everyday sustenance, the rat race, and the grind.”

but by the end of the break, it was crystal clear to me that I was ready to move on to a new adventure.” Several weeks into his sabbatical, he stopped checking his email: “My heart was no longer in the work. I didn’t yet know what I wanted to do next, but I knew it was time to shake things up.”

Part of this is driven by financial firms, which spend millions on advertising campaigns showing happy elderly people smiling as they walk through beautiful meadows. The message? Work hard and invest until you reach the “magical number.” Then you can stop and smell the roses.

On the pathless path, retirement is neither a destination nor a financial calculation, but a continuation of a life well-lived. This shifts attention from focusing on saving for the future to understanding how you want to live in the present.

he designed his own mini‑retirements, trips of “one to six months” where he would test out living in different ways. He described these as an “anti‑vacation” and “though it can be relaxing, the mini‑retirement is not an escape from your life but a reexamination of it—the creation of a blank slate.”

I try to think about time in blocks of one to three months and within each block, I pick one or two things I want to prioritize and test. It might be living in a different type of place, working on new projects, traveling, or learning something new.

The spirit of the mini‑retirement is not about escaping work. It is about testing different circumstances to see if you want to double down on them or change directions.

testing out different ways of structuring my life now is a win‑win proposition. I’m lowering the odds that I’ll be unhappy in the future all while crafting a life I’m more and more excited to keep living.

While I’m still saving for retirement, I’m not putting all my faith in reaching certain financial milestones as the most important thing. I’m much more focused on spending time and money now to experiment with different modes of living such that when I reach the latter stages of my life, I won’t be making a dramatic shift in life priorities, but continuing on the pathless path.

John Stuart Mill was giving similar advice, arguing that societies need people to embrace their individuality and perform “experiments in living.” He argued that such experiments are vital to the pursuit of knowledge and that cultures only learn and evolve when original approaches to living are discovered. Mill wanted people to act on their inspiration because “the worth of different modes of life should be proved practically when anyone thinks fit to try them.”

if societal norms are too strong or rigid, original thinkers who would otherwise experiment will be stifled. He argues that trying to constrain these people is also not worth doing because they already struggle, “fitting themselves, without hurtful compression, into any of the small number of molds which society provides.”

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.”

When I became self‑employed, I was disoriented because the people paying me for the projects didn’t care when and how much I worked. They just wanted their problems solved. It was up to me to figure out how to spend my time.

Working on my own, I had infinite degrees of freedom to shape what I worked on, who I worked with, and how much I worked. When people on the pathless path first discover this possibility, it can be jarring. Opting out of work and opting in to other aspects of your life can create questions about who you used to be.

“money is something we choose to trade our life energy for,” it is nearly impossible to give up your time for money without thinking deeply about the trade-offs.

the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is. Money might help pay for therapy, time off, and healing retreats, but it won’t help you come to a place where you really trust and know that everything will be okay.

Having faith does not mean being worry‑free. I still worry about money, success, belonging, and whether I can keep this journey going. However, I’m able to recognize that the right response is not to restructure my life to make these worries disappear. It’s to develop a capacity to sit with those anxieties, focus on what I can control, and to open myself up to the world.

A person is successful if they have followed their own interests and talents to become the best they can be at what they care about most.

the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness.

we find ourselves feeling empty, and the easiest way to deal with this is to ignore the feeling and ratchet up the goal. More money, a bigger house, a new car, a higher salary, an executive position at a company, or a larger retirement nest egg.

“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.”

the “second chapter of success” in which you shift your mindset from what you lack to what you have to offer, from ambition to aspiration, and from hoping that joy will result from a specific outcome to experiencing it as a byproduct of your journey. People are reluctant to flip the page to the second chapter of success because it requires rejecting paths that are not only more accepted but also promise money, respect, and admiration.

defines prestige as “the kind of status we get from doing impressive things or having impressive traits or skills.”

far too many young people believe learning how to hack bad tests is a necessary part of success. In his work with entrepreneurs, he struggles to convince them that they don’t need to play these games.

When you’ve spent your entire life studying for the test and compiling long lists of achievements it can be hard to believe that true success is that simple.

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.

there are other good eggs, such as the ones from Hunt’s farm, which are often dirty, come in various shapes, and don’t need to be refrigerated. Many people see these as bad eggs, but Hunt knows the truth, that they are “one of the best things in life.”

On the default path, you are automatically a “good egg.” On the pathless path, people default to seeing you as a “bad egg.”

embracing the pathless path requires grappling with the feeling of being a “bad egg.” This often drives people who leave the default path to eagerly embrace new identities that are still recognizable as legible to the “traditional” economy. They gravitate to titles like a startup founder, entrepreneur, freelance consultant, or even the newly emerging “creator.”

The pathless path is about ignoring the pull of needing to be a “good egg” and learning what truly enables you to thrive. What this really means is developing an appreciation for discomfort.

The comfort we feel when we do what is expected keeps us from developing the skills we need to face uncertainty.

“losing things is about the familiar falling away,” but “getting lost is about the unfamiliar appearing.”

“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.”

If we don’t define “enough,” we default to more, which makes it impossible to understand when to say no.

What I’ve discovered in conversations is that no matter how much money people have, they will go to enormous lengths to avoid any discomfort related to their financial situation. This is what makes quitting full‑time employment seem terrifying and a steady paycheck so addictive.

He argues that “if everyone honestly admitted his urge to be a hero it would be a devastating release of truth.”129 What he means by heroic is less about saving the world and closer to the pathless path: a journey of finding yourself, grappling with your insecurities, and daring to seek out a life that is uniquely yours. Becker argues that prescribed paths of the modern world can trap people into conforming to the expectations of others instead of taking steps to create their own unique path.

Instead of playing to not lose, I’m playing to win. Behind our money fears are existential fears, like the fear of death or the fear of not being loved, respected, and admired. These fears are likely not solvable but we can learn to coexist with them.

There’s so much more to who you are than you know right now. You are, indeed, something mysterious and someone magnificent. You hold within you – secreted for safekeeping in your heart – a great gift for this world. Although you might sometimes feel like a cog in a huge machine, that you don’t really matter in the great scheme of things, the truth is that you are fully eligible for a meaningful life, a mystical life, a life of the greatest fulfillment and service. – Bill Plotkin

the “conversational nature of reality.” He believes all of us have an ongoing “conversation” with the world. While this may play in literal conversations with others or ourselves, it can also be metaphorical. What I’ve taken it to mean is that we all have things we are meant to find out about ourselves and the only way to discover them is to open ourselves up to the world.

the conversational nature of reality. It’s an acknowledgment that there are deeper forces at play in the world and we are a tiny little part of all that magic. It’s about existing within that magic and still daring to ask questions about what matters or where you fit in.

You may feel the urge to tell everyone about your new insights, questions, and curiosities, but this can be a mistake. Your ideas may make others uncomfortable and any doubt, skepticism, or criticism they express could convince you to run away from the frontier.

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.