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.

I listed a few other paths that he conceded were possible, but he added, “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.

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.

Peter Thiel, born right after the baby boom generation, reflected on this mentality in his book Zero to One, saying, “Since tracked careers worked for them [the baby boomers], they can’t imagine that they won’t work for their kids, too.”

The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything. – David Foster Wallace

If there are clear boundaries to behavior within a given field of endeavor, then there is also great freedom to adapt and imagine within those lines. These boundaries, however, should always be tested to see if they are actually still real. It takes conscious acts by individuals to test these edges. – David Whyte

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.

“How are you complicit in creating the conditions you say you don’t want?”

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

arriving each morning at the 7 train subway platform. I boarded the train for the single-stop journey from Queens to Manhattan. Then 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.

The idea of total work was inspired by the German philosopher Josef Pieper, who first wrote about it in his book Leisure, The Basis of Culture. Writing in Germany after World War II, Pieper was shocked at how people were eager to throw themselves into work without pausing to reflect on what kind of world they wanted to build.

We work to earn time off and see leisure as a break from work. Pieper pointed out that people “mistake leisure for idleness, and work for creativity.” 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.”

“If work dominated your every moment, would life be worth living?”

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

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.62 I would have thought this completely absurd if I had not felt the depths of my connection to the world in those months.

For most people, life is not based on all‑or‑nothing leaps of faith. That’s a lie we tell ourselves so that we can remain comfortable in our current state. We simplify life transitions down to single moments because the real stories are more complex, harder to tell and attract less attention.

Uncertain Discomfort + Wonder > Certain Discomfort

When people reflect on their lives, these are the things that people regret most – not moving towards their ideal selves.

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.

Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.”69 This is in contrast to an ambitious journey where we already know what we value. For example, someone who wants to make a lot of money already values money. They don’t need to learn why they want it along the way. An aspirational journey is more ambiguous, and it is harder to predict what sort of values we will adopt along the way.

During my first few years of self‑employment, these fears overwhelmed me, but 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.

nothing good gets away, as long as you create the space to let it emerge.

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. – Rolf Potts

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.

the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is.

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.”

Many people realize they are on the wrong path after achieving impressive milestones.

Being a ‘millionaire’…nothing. It’s a trick of evolution that drives us, and no one is immune from making this mistake.”103 This is what Harvard professor Dr. Ben‑Shahar calls the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness.

“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.

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.

However, he continues, over the last 50 years the need for people to be “legible” and fit into a standard model of work has merely become “industrially preferable.” This puts government and institutional leaders in a position where they are incentivized to convince people that following rigid paths in their institutions is the correct path for everyone. Hunt uses the example of the “industrially necessary egg,” to make his point. “Good” eggs are those that meet specifications, are perfectly clean, and can legally be sold in a supermarket. Any farmer knows, however, 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.”

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.”

very few people would ever consider walking into their manager’s office in September and declaring, “I’ve made enough money for this year. See you in January!” Instead, it is easier to accept the economic logic of profit‑seeking organizations, that “more is better,” and apply it to our own lives.

American anthropologist Ernest Becker was convinced that most of our actions in life are driven by a fear of death. 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.”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.

We are always falling in love or quarreling, looking for jobs or fearing to lose them, getting ill and recovering, following public affairs. If we let ourselves, we shall always be waiting for some distraction or other to end before we can really get down to our work. The only people who achieve much are those who want knowledge so badly that they seek it while the conditions are still unfavorable. Favorable conditions never come. – C.S. Lewis

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.

According to Robert Kegan, a psychologist at Harvard, we are shifting away from a world where we need to fit in towards one where we must develop the skill of “self‑authoring.”137 Instead of looking to external cues to learn how to live, we need to have a coherent internal narrative about why we are living a certain way. This is the ethos of the pathless path and if you don’t know or understand your own story, you will struggle.

She defines shame as “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging.” She believes that most people give too much power to this emotion when making life choices.”138 She doesn’t think we can “solve” shame and suggest that people pay attention to a slightly different emotion, guilt. She defines guilt as “holding something we’ve done or failed to do up against our values and feeling psychological discomfort.”139 In contrast to shame, guilt is actionable. The disconnect between what we claim to care about and what we do (or don’t do) points out what matters to us. Guilt drives many people to work, and this is a normal reaction to this uncomfortable emotion. Most people want to contribute, help, and engage with the world. However, sometimes this impulse gets hacked by our shame and we follow paths that aren’t ours because we feel like the world’s love depends on us doing a certain thing. We are afraid that if we step away or make a change, we might be cast out of our family or community. This is one of life’s most terrifying feelings and keeps many from making changes. Yet if we learn to recognize this reaction, we can quiet the voice of shame and use our guilt in a healthy manner to guide us towards things we claim to care about.

“humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.”

To thrive on the pathless path, we must ignore the shiny objects and distractions and strip away the stories that are not our own to remember who we are.

On the default path, promotions, job changes, and raises serve as visible markers of success. However, my proof of success is hidden, coming in the form of messages I receive in my email or conversations with people who are inspired by my work.

if your success is not on your own terms, if it looks good to the world but does not feel good in your heart, it is not success at all.

Instead of embarking on an endless search, I’ve taken a different approach: working backward. Instead of thinking about what I want to do and how I want to live, I start instead with what I don’t want to be doing and what failure looks like.

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 a world where we are pushed to “regard our personal qualities and the result of our efforts as commodities that can be sold for money, prestige, and power,” engaging in a creative endeavor allows us to find value in the act itself.157

Before I left my job, I was exploring my creativity but did not feel the deeper connectedness that Fromm wrote about. I was convinced that escaping my job was the most important thing I had to do. However, soon after achieving the “freedom from” traditional employment, I discovered the vastness and challenge of developing a positive side of freedom.

Ultimately, figuring out what to do with freedom once we have it is one of the biggest challenges of the pathless path. Writer Simon Sarris argues that we can only do this by increasing our capacity for agency, or our ability to take deliberate action in the world. He argues, “the secret of the world is that it is a very malleable place, we must be sure that people learn this, and never forget the order: Learning is naturally the consequence of doing.”158 In other words, only by taking action do we learn and only by learning do we discover what we want. Without this, we will struggle to take advantage of the freedom that the pathless path offers.

The pathless path is the deliberate pursuit of a positive version of freedom. Revisiting Fromm’s definition, “the full realization of the individual’s potential, together with his ability to live actively and spontaneously,”

I’ve found no better advice than the following from Dolly Parton: “Find out who you are and do it on

Researchers call this the “end of history illusion.” Across all age groups, people indicate that they have experienced profound change in the past but when they forecast their future, they don’t see the trend continuing.