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

by Paul Millerd

I read through feedback reports from people throughout the company and created summarized reports of each executive’s strengths and weaknesses. 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. 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.

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.

“I don’t know anyone who has done that.” Many people fall into this trap. We are convinced that the only way forward is the path we’ve been on or what we’ve seen people like us do. This is a silent conspiracy that constrains the possibilities of our lives.

“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?”

This phase of writing and creating was thrilling. It was a sharp contrast with my day job where I was working hard, but only in safe, predictable ways.

A passage from William Reilly’s book How To Avoid Work, published in 1949, captures my reality at the time: 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.⁠

In business school, I created a vision of the kind of leader and person I wanted to be, and five years later I realized I was headed in the wrong direction. When I wrote that paper, my model of the world was one in which my principles would triumph over my environment. If those principles still mattered to me, which they did, I needed to get more creative about how I could bring them forth in my life and career.

So much of life is like this. We are surprised at the moment something happens, but looking back, we realize that everything makes sense.

I slid my body into the masses of people and became part of a massive blob of workers making our way into the mecca of work. Each day I searched for signs of life. I would force a smile and look around to see if anyone noticed. No one ever did. So I gave up and adopted the neutral uninterested smirk that everyone seemed to understand was the proper way to be.

During the first few months of self-employment, I read an article that jolted my reality. Titled, “If work dominated your every moment, would life be worth living?” the philosopher Andrew Taggart offered a powerful question that spoke to the underlying tension I lived with for most of my adult life.

To Pieper, leisure was above work. It was “a condition of the soul,” and the “disposition of receptive understanding, of contemplative beholding, and immersion – in the real.”⁠

Similar to expectations around meaningful work, far too many people limit their imagination of work worth doing to things that either come with a paycheck, require qualifications, or have a socially accepted story of impact. If I limited myself in the same way I would have lost all energy to continue. 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.⁠

I knew what it felt like to work “differently” and make money on my own, and I learned to appreciate the “spirit of the fool” on an uncertain path. This was powerful because it helped me expand my perception of what I thought possible.

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. Play this game long enough without becoming too burned out and you might end up getting promoted.

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.

Aspirational pursuits go hand in hand with the pathless path because they can appear incomprehensible to others and even yourself, sometimes for years. Callard argues that the aspirant’s understanding of the value of their pursuits “is characterized by a distinctive kind of vagueness, one she experiences as defective and in need of remedy.”⁠

Learning to exist with this vagueness is vital, especially at the earliest stages of making a change. It’s worth it though, because as Callard says, what is really at stake is you are “learning to see the world in a new way.”

Due to lingering health issues, I sometimes go long stretches with very little energy. Reminding myself that this is a fact of life, like gravity, helps me accept the uncertainties of life and the pathless path.

What could be some benefits of an attempt or partial success? What is the cost of inaction in three months, 12 months, and in a few years?

People who value comfort and security often cannot understand why anyone would willingly pursue a path that increases discomfort and uncertainty.

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.⁠

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.”⁠4 So I might add to Steinbeck’s advice: nothing good gets away, as long as you create the space to let it emerge.

Often we don’t notice our drift into a state of low‑grade anxiety until we step away from what causes it, as I noticed the first day after I quit my job and realized I was burned out.

Mohit, Kevin, Jacqueline, Edward, Lenny, Alex, and I were all surprised by how different life feels when it is not structured around work. We also became aware that our previous paths had kept the possibilities for our lives hidden, and in a short time, we started to recapture a youthful energy, one that enabled us all to take bold steps towards different kinds of lives.

The more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we’re too poor to buy our freedom.

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. My goal is to test my beliefs to get a better understanding of what really makes my life better. Many people say things to me like “I could never live like you do!” All I can think, however, is “have you tested that?”

Rao argues that the answer is not to abandon goals altogether but to take them more seriously and to put more thought into identifying unique fixed points, ones that align with the things that bring us alive.

Mill argued that conventional ways of living tend to “degenerate into the mechanical’’ and that 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.”⁠

Technology and increased prosperity make this the best time in our history for our own “experiments in living.” Yet Mill, who was frustrated in his time with how many people seemed “satisfied with the ways of mankind as they now are,” might be surprised at how much shame is still associated with taking a different path.

When everyone you know builds their lives around a steady paycheck, it is easy to lose track of what we give up for that paycheck and forget that for most of history this was not a normal state of affairs.

No amount of money can buy the peace of mind that comes with finding a path that you want to stay on. Once we know, as Vicky Robin argues in her book Your Money or Your Life, that “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. As the spiritual teacher Sharon Salzberg has written, “whatever takes us to our edge, to our outer limits, leads us to the heart of life’s mystery, and there we find faith.”⁠23 This is the essence of the pathless path, and the only way to develop room for faith in your life is to do exactly as Salzberg says, explore the limits and step into the possibilities for our life. The fact that the next steps are unknown to us is exactly the point.

People have the notion of saving the world by shifting things around, changing the rules, and who’s on top, and so forth. No, no! Any world is a valid world if it’s alive. The thing to do is to bring life to it, and the only way to do that is to find in your own case where the life is and become alive yourself.

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.

Now it’s easier than ever to open your computer and opt-in to a community that defines prestige, status, and success in a way that matches how you want to design your life.

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.⁠14 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 longer I’ve stayed on this path and the more effort I’ve put into connecting with people heading in similar directions, the better my life has become.

Early on, it was clear that if I continued to share over a long enough period of time, it might radically improve my life. As I’m writing this book, I can say without a doubt that my hunch was correct.

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. Howard Gray, a consultant and storyteller, and veteran of the pathless path, sees the uncertainty of his path as a positive thing. When his life “stops moving and it calcifies or solidifies, that’s a bad thing” and he’s on the right track when it’s a “formless, evolving thing.”⁠

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

Because I work for myself, I spend zero minutes a year blaming other people for my circumstances. It forces me to take complete ownership of my life and continue to experiment, reflect, and try again. In six months I can experiment with my life in many more ways than I did in the ten years I spent on the default path, allowing me to learn much more quickly.

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

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

Behind my money fears was a longing to feel that my life mattered. I suspect this is the same for many, and money is one shortcut we use to “prove” our worth. Yet in my experience, no amount of money ever seems to satisfy. Becker argues that the only way to transcend these existential fears is to live a life that feels heroic. He argues that “if everyone honestly admitted his urge to be a hero it would be a devastating release of truth.”⁠

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.

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

The conversational nature of reality is most apparent when you are willing to exist at “the frontier” of your current reality. As Whyte reflects, “It’s astonishing how much time human beings spend away from that frontier.” The default path keeps people from this frontier but the pathless path pushes you towards it. To Whyte, the cost of not moving towards the frontier is profound, as we often risk missing out on a “deeper, broader, and wider possible future that’s waiting.”⁠

Being at the frontier of your current reality is disorienting. Deep down you might have a sense that you should keep going in a certain direction, but you never know why.

This is what Whyte means when he writes about 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. Much of my previous life had been scripted into a routine and I spent almost all my time knowing where I was supposed to be. This short‑circuited my curiosity for years and kept me from seeing that there was a “conversation” with the world to be had at all.