Notes on Pathless Path

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My Introduction

First, a look at the description of Paul Millerd’s book Pathless Path:

The Pathless Path is about finding yourself in the wrong life, and the real work of figuring out how to live. Through painstaking experiments, living in different countries and the goodwill of people from around the world, Paul Millerd pieces together a set of ideas and principles that guide him from unfulfilled and burned out to the good life and all of the existential crises in between. This book is a personal journey of awakening and is an ideal companion for people considering leaving their jobs, embarking on a new path, dealing with the uncertainty of an unconventional path, or searching for better models for thinking about work in a fast-changing world.

Heavy stuff. Especially if you find yourself gazing at your shoes at work. Or if you are a student who doesn’t know what they want to do. This book is excellent. You can find my praise in the Amazon review:

My Amazon review

This book is about designing an embodied life. A life that embraces calculated chances because that is what living is. You get one life. You can order off the menu. By facing your fears and being honest with yourself, you can start to say no. You can reject, what Ramit Sethi has called “invisible scripts” and write your own.

If any of this sounds cliché, it’s because the question of how to live a life is as old as philosophy. And yet, Paul Millerd, in 2022, has published the sum of his story in such a way that it adds to the conversation. More than ever, its message is relevant and practical.

Paul writes a deeply personal narrative that takes him from the familiar to the “pathless path”. There are waypoints where Paul weaves his feelings to those of prior thinkers, artists, and rogues who came to the same broken bridge where most will not pass but for those who stir from within there was no choice. They had to leap.

If you have questioned your own path, or a nagging lack of intention in your choices you need this book. If you have felt a gradual loss of agency in your direction you need this book. You are in the grip of an invisible script that was not written for you.

Paul shines a blacklight on the script. And shows you how to find your own.

I have had the privilege of speaking with Paul over the years at an opportune time. I left my career after 21 years and more soul-searching than I’m fully comfortable admitting. This book is the result of the hundreds of conversations Paul has had across the world. He’s sharp, well-researched, and deeply compassionate.

This book does not beat you over the head. It invites you to rediscover what you’ve lost. The feelings you sacrificed in pursuit of...well, whatever it is you are chasing. It exposes miswanting. The things we think we want that are just proxies for what we truly want. We have lost the ability to tell the difference. This book is a reminder.

Perhaps after reading it, you will feel more dedicated to your current path. If your current path survives the book’s inquiry, then you will have attained a valuable victory — reassurance and red-hot conviction.

But if you find yourself nodding along with Paul’s journey then you will find the book invaluable. It holds a roadmap to a path that itself has no map. It will show you how to embrace your instincts again. Re-connect with who you are. Your family, friends, and community need you fully here. You need you fully here.

Paul has amassed a collection of beautiful quotes but my favorite comes from none other than Dolly Parton and captures the essence of what Paul will teach you:

“Find out who you are and do it on purpose”

I’ve sent the book to several people. I marked up my hardcopy and then decided to get a Kindle copy to make it easier to copy and past excerpts. This document is a collection of excerpts re-factored by topic and interspersed with my commentary.

This document is meant to memorialize my takeaways but is not a substitute for reading what is a profoundly personal story. A story that vibrates with personal agony.

Please consider buying a copy.

I’ll even buy you a copy if you promise to tell me what you learned from it :-)

Invisible Scripts

Author Ramit Sethi describes “invisible scripts” as:

truths so ubiquitous and deeply embedded in society that we don’t even realize they’re guiding our attitudes and behavior. Like water to a fish, they surround us even if we don’t know it. This is a topic that doesn’t get discussed often. Mostly because invisible scripts are revealing. And the things they reveal might be some tough pills to swallow.

Paul’s use of the term “script” is effective. It’s a not-so-subtle reminder that we should wonder if we are living our lives or are we actors playing the role of someone else’s life. A role that was not written for us. I’m old enough to remember that questions like that comprise a good portion of 80’s arena rock lyrics.

If rebellion is a hallmark of youth and hair bands, then when do we become our parents? At some point, we start taking our cues from the societal reinforced by what Holly Mandel calls the “should computer”. You should do this. You should do that.

This excerpt pulled from the book’s conclusion shows how Paul is helping you re-widen your values:

Here are some of my assumptions, many of which have been sprinkled throughout this book: Many people are capable of more than they believe. Creativity is a real path to optimism, meaning, and connection. We don’t need permission to engage with the world and people around us. We are all creative, and it takes some people longer to figure that out. Leisure, or active contemplation, is one of the most important things in life, There are many ways to make money, and when an obvious path emerges, there is often a more interesting path not showing itself. Finding the work that matters to us is the real work of our lives. The pathless path is about opening yourself up to this emergence. It’s about growing up and letting go. It’s about realizing that if I claim to care about something, I need to be willing to act, and also be willing to be wrong. I must let go of my ego and my need to be seen as a “successful” person. After reading this book, you should no longer be able to look at your current path and think, “this is definitely the only way.”

While the book is properly organized as a flowing narrative, I’ve assembled this reference around the idea of scripts.

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Moontower Reference To Paul Millerd’s The Pathless Path

Are These Scripts Unnatural?

In Mexico, I overheard a conversation about hiring locals: “You can’t pay people too much because they’ll stop working!” The idea that people might decide to work less is hard for some people to imagine.

[Me: This reminds me of an Egyptian-American friend’s experience when he tried to build a business in Egypt.]

So where do our modern notions of work come from?

A brief history of work beliefs

We see this articulated by 13th-century Catholic priest Thomas Aquinas, as he argues “labor is only necessary ‘naturali ratione’ [by natural reason] for the maintenance of individual and community.” People should be expected to work, but the reason is to meet the needs of our families and communities. In the 1500s, Martin Luther and John Calvin expanded this definition as part of what is now known as the Protestant Reformation. They had grown disappointed in religious leaders and attacked them for living idly in monasteries. Their angle of attack was one’s relationship to work. Max Weber summarizes the shift, saying that the way to honor God, “was not to surpass worldly morality in monastic asceticism, but solely through the fulfillment of the obligations imposed upon the individual by his position in the world. That was his calling.” With the introduction of a “calling,” Luther and then Calvin both wanted to undermine the authority of the Catholic Church to govern an individual’s relationship with God.

Calvin paired Luther’s increase in individual freedom with the idea that everyone is predestined to serve God through a specific calling. Working hard in the area of one’s calling determines the status of a person’s relationship with God.

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.

When entrepreneur Gary Vaynerchuk tells us in his book Crush It to “wake up before everybody else and work into the night. Hustle,” he accepts both the duty of work and absolute commitment to work as integral to life. Oprah Winfrey channels a modern spin on Calvin’s calling, arguing that “each of us has a personal calling.” To her, the “best way to succeed is to discover what you love and then find a way to offer it to others in the form of service, working hard, and also allowing the energy of the universe to lead you.” These Catholic and Protestant perspectives on work are deeply embedded in the modern default path view of work that spans the globe but has become detached from the time periods and traditions from which they emerged.

Religious scholars point out that the Protestant “work ethic” is more than a blind obsession with work. It is paired with thrift, self-discipline, and humility. Yet as fewer people look to religion for wisdom on how to navigate life, they are only left with the watered‑down version of these views.

The 20th Century Anomaly

Professor Raj Chetty at Harvard found that nine out of ten people born right after World War II did better economically than their parents. Over time people came to expect constant advancement in their lives. John Steinbeck captured the sentiment in his book America and Americans in 1966: No longer was it even acceptable that the child should be like his parents and live as they did; he must be better, live better, know more, dress more richly, and if possible, change from father’s trade to a profession. This dream became touchingly national. The baby boomer generation was born in the middle of this period, came of age at the tail end of it, and rose to leadership in global institutions by the end of the 20th century. By the time I graduated from college in 2007, the idea that life should be built around a good corporate job was so sacred that almost everyone had forgotten that only 100 years earlier most people worked on farms.

Asset manager, writer, and baby boomer Jim O’Shaughnessy argues that this approach to life is flawed and his generation’s mistake was to assume that the path’s that worked for them would work forever:

We made a mistake and by that, I mean my generation and my parents’ generation. The mistake we made was thinking that the period from 1946 to 1980 was the norm. No, it was not! It was the anomaly! We had just wiped out the manufacturing capabilities of anyone who could challenge us. So, the idea that you had that job with the gold watch, and you could work there for your entire career and raise a family of four and all of that, that was an anomaly.

During that stretch of time, it would have been a mistake to opt-out of the default path because as Thiel points out, “whether you were born in 1945 or 1950 or 1955, things got better every year for the first 18 years of your life, and it had nothing to do with you.”

How do these beliefs manifest today?

As I was growing up, work was such an obvious goal of life that I never paused for a moment to question it. Adults talked about work all the time and constantly asked me what I wanted to do when I grew up. Schools reinforced this perspective and we learned to study hard to earn good grades to get a good job. As I grew older, I was convinced that a good career was the most important thing in life. Later, I was shocked to learn that for most of human history, this was not the case.

It wasn’t until my early 30s that I started to suspect something was amiss. Like many of the people I knew, I was single, renting, and living and working in a city away from my hometown. Those who were starting families were overwhelmed with the costs of daycare, healthcare, and housing. We entered adulthood thinking we could copy‑and‑paste what our parents had done, but it was more complicated than that. Factors that support meaningful lives, like economic growth across all sectors, a young population, two‑parent households, generous pensions, and company loyalty were anomalies of the past, as O’Shaughnessy points out.

Sociologist André Gorz spent the latter half of the 20th writing about the role of work in society. He argued that many countries had evolved into places where the primary way one gained “membership” in society was through formal work. He called these places “wage-based societies” where the central ethic was, “never mind what work you do, what counts is having a job.“

Seeing the job as a central element of a good life and employment rates as a metric of a successful society was not a common assumption until after World War II. In 1946, the United States formalized this by passing the Full Employment Act “to promote maximum employment.”

One striking example is from 2009 when U.S. President Barack Obama explicitly mentioned jobs as the reason why he did not want to pursue a more ambitious healthcare policy: Everybody who supports single‑payer healthcare says, ‘Look at all this money we would be saving from insurance and paperwork.’ That represents 1 million, 2 million, 3 million jobs of people who are working at Blue Cross Blue Shield or Kaiser or other places. What are we doing with them? Where are we employing them?40 Regardless of whether single‑payer healthcare would have improved lives or not, this decision shows that, at least in the United States, government leaders prefer to create or save jobs rather than doing anything that risks losing them.

For most people, having a job is better than not having a job, and the costs of unemployment are well documented in academic studies.

From my perspective now, I had no future at the company, and by the time I had that conversation about my performance with my manager, things were already headed south. Yet I was still working hard on my proposal for promotion, outlining a multi‑year career path for my position. Based on the experiences of others who leave the default path, this stage of contradiction is common. You take a last stand, doubling down on the existing path despite all evidence that it is no longer working. 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.

Why The Scripts Are Hard To Escape

The ease of having an ambition is that it can be explained to others; the very disease of ambition is that it can be so easily explained to others. – David Whyte

Zen philosopher Alan Watts argued that “the desire for security and the feeling of insecurity are the same thing,” and that “we look for this security by fortifying and enclosing ourselves in innumerable ways. We want the protection of being ‘exclusive’ and ‘special.’ This was exactly what I was looking for.

[Me: I have felt that idleness or rest can counterintuitively induce anxiety and restlessness. My sense is that as time passes from our most recent wins or accolades, our insecurity creeps in. It tells us, “go out there and be significant”]

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.”

[Me: This is a great essay. I’ve written about it before:

My mother was very big on the lesson of not caring what other people think. We try to seed an inner compass in our children before the peer pressure years arrive. The winds of influence will inevitably spin them around, and hopefully, they stagger out of those years facing North. This classic essay by C.S. Lewis is an articulate exposition of the psychology, danger, and futility of chasing the “inner ring.

I’ve highlighted my favorite excerpts here. ]

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.”

Burnout

Professor Cary Cherniss’ definition of burnout as “the bureaucratic infringement on a professional’s autonomy” and thought that the right way to think about burnout was to focus on the disconnect between an individual and the culture of the company in which they worked.

[Me: best definition of burnout I’ve ever seen...replace “company” with “industry”]

What if the individual professional seeks to live up to the external, organizationally imposed criteria of what constitutes success and achievement, but is unable to do so?

People dedicate themselves to being “good workers,” and being successful means keeping clients, customers, and managers happy while fitting into a company’s cultural norms. Unfortunately, success for the company does not always align with what is best for the person, and over time, a disconnect can emerge. This is what happened to me. At that last job, I wasn’t a team player and I could have tried harder to say the right things, dress the right way, or spend more time pleasing my manager. But I couldn’t do it. The norms of the organization were pulling me too far away from the person I wanted to be and the energy I used to manage this disconnect undermined anything good I had to offer.

A German report on burnout found that when burned out, people “may start being cynical about their working conditions and their colleagues…” and may “…distance themselves emotionally and start feeling numb about their work.” This is the tricky thing about burnout. If you are suffering from burnout, you are likely not thriving at work, and over time it’s easy to see yourself as the cause. Add to this the common assumption that you should never leave a job too soon and you get a world in which millions of people are experiencing the slow, marginal creep of burnout and have no way out.

Why You Must Follow Your Own Script

"To venture causes anxiety, but not to venture is to lose one’s self... And to venture in the highest sense is precisely to become conscious of one’s self." —Kierkegaard (via @visakanv)

The author Gretchen Rubin decided to override her “ought to” self when she said, “I’ve come to a point where I’d rather fail as a writer than succeed as a lawyer, and I need to try and fail or try and succeed, but I need to do it.” Rubin attended Yale Law School, clerked for Sandra Day O’Connor on the Supreme Court, and was at the start of a high‑paying and promising law career. Yet, she understood that if she kept going and never took a chance on becoming a writer, she would regret it.

Aspiration

Agnes Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.” 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.

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.”

It Can Be Lonely

The pathless path, however, offers a unique invitation to grapple with our insecurities. If we can accept the invitation, we can continue to ask and then hopefully answer questions about what we really want.

Will They Still Love You?

I felt under attack and that I had disappointed the people that mattered most. My parents had sacrificed so much for me and I felt selfish. Now I know they were coming from a place of love and concern and didn’t want to see me suffer. But then, instead of sharing my own fear and uncertainty, I tried to convince them that my evolving vision of the pathless path was the best approach to life. 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.

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.

[Me: Before I left my career, I expressed unease about the change to a friend. He asked me, “Are you afraid it’s the wrong choice, or are you afraid of how others will think of you?” I replied, “I’m certain this is what I need. That’s easy. I’m concerned about what I tell others.”]

The Weight Of Baggage

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. When I arrived in Taipei, I was lost in both the story of my life and in this new place where I couldn’t read the signs or speak the language. Yet I also felt I was exactly where I was supposed to be, my days filled with lightness and ease. This feeling contrasted with the daily tension and low‑grade anxiety that I had experienced in New York and Boston over the previous ten years.

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. The Chinese philosopher Lao Tzu wrote about this more than 2,500 years ago in the Tao Te Ching: “Less and less do you need to force things until finally you arrive at non‑action. When nothing is done, nothing is left undone. True mastery can be gained by letting things go their own way. It can’t be gained by interfering.”

John Steinbeck channeled this sentiment in a letter to his son, telling him, “If it is right, it happens—The main thing is not to hurry. Nothing good gets away.”

[Me: What a beautiful statement of faith]

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

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. In Taiwan, I was able to embrace a state of doing nothing that was not filled with anxiety and tension, but reflective and open. The possibilities that started to emerge at this time have changed my life. After more than three decades of constantly planning for the future, I was able to start living in the present.

First, people become aware of their own suffering. 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.

Rediscover Your Intentions

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

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 is not an indulgence or a luxury. It’s required in a changing world.

Here’s a question for you: do you think the next forty years will see more or less change? When we think about the future, we tend to underestimate how much things will change, especially for ourselves. 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. People believe that “the pace of personal change has slowed to a crawl and that they have recently become the people they will remain.”

The pathless path is an alternative to how many people deal with change: by denying, delaying, or rejecting it. As we age we do become more mentally rigid and minor challenges to our routines can be landmines threatening to blow up our weeks, and suggestions that we live in new ways are treated as acts of war.

Moving abroad, running my own business, and living in more than 20 places in only a few years have made me much more resilient to change and more aware of my own default to become rigid in my thinking.

I’ve come to see reinvention as one of the most valuable meta‑skills worth developing, and on the other side of these experiments, I am often much more relaxed and confident than before.

Yuval Harari argued that “in order to keep up with the world of 2050, you will need not merely to invent new ideas and products, but above all to reinvent yourself again and again.”

In the 1970s, academic turned farmer Wendell Berry wrote about how economic success includes the hidden cost of depriving people “of any independent access to the staples of life: clothing, shelter, food, even water.” What was once the riches of self‑reliance have become things with a price.

Tim Wu made this point in a widely read essay titled “The Tyranny of Convenience,” where he argues that convenience, “with its promise of smooth, effortless efficiency…threatens to erase the sort of struggles and challenges that help give meaning to life.” Wu argues that many see convenience as a form of liberation. People aim for “financial independence” only to realize when they achieve it that they’re only independent in the narrow sense of being able to pay for everything.

[Me : We have anxiety about our distance from self-reliance. When our prosperity depends on a whimsical system. The sense that if we were born in another era or another place we might have had no chance at advancement. I often think about this interview response by hedge fund manager and one of the greatest Magic The Gathering players of all-time, Jon Finkel:

I think I’m a bright guy, but I’m also aware of how much of my success has been luck. I was born a white man to upper middle class parents in the wealthiest country the world has ever known. I had a very specific set of skills that are easily translatable into money in our current society, but would have been far less useful for most of human history. The game I got obsessed with happened to grow and expand into the enormous thing magic has become, and it just so happens that I was actually good at it. So basically, I don’t think I have an edge in everything at all. I think I had a couple specific intellectual skills and it just so happens that they’re most obvious in the games that all the smart people I know also play, so it makes me look more talented than I really am.

In no era in history has brawn mattered so little as it does today. This should humble most of us desk jockeys.]

Wisdom From The Classic Tuesdays With Morrie:

In one significant quote, Morrie reflects on the difference between living and dying:

“Dying 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.”

If the culture doesn’t work, don’t buy it. Create your own. This is what the pathless path is all about. It’s having the courage to walk away from an identity that seems to make sense in the context of the default path in order to aspire towards things you don’t understand.

[Me: In my own family we are deliberate about creating a culture centered around 3 values. They are like a coat of arms without a shield: kindness, gratitude, curiosity]

How To Follow Your Own Script

Find out who you are and do it on purpose. — Dolly Parton
“Critical thinking without hope is cynicism. But hope without critical thinking is naïveté.” — Krista Tippet

With these quotes in mind, let’s see how we find our own scripts.

Acknowledge your waypoint

Carl Jacobi. He told his students to “invert, always invert,” encouraging them to approach difficult problems by inverting the equation to gain a new perspective. We can also apply this principle to our lives. For example, instead of asking what makes up an amazing life, we first define the worst‑case scenario and then work backward. What does a miserable life entail? What actions would make achieving such a life more likely? Then figure out how you can avoid these things from becoming true.

During my time on the default path, I often imagined a future version of myself that I knew I didn’t want to be: an overweight guy in his 50s who barely tolerates the people in his life, hates his job, spends his days in a windowless cubicle farm, and isn’t very happy. If you had known me then, you would have said I would never have ended up like that. However, by the time I left my job I was much closer to that person than when I started.

On the pathless path, I take this exercise much more seriously. While the grumpy guy in the cubicle is even harder to imagine now, there are still aspects of him that I want to avoid. Here is my current sketch of the person I don’t want to be ten years from now: Paul is still committed to the pathless path, a fact that still draws skepticism from other people. He has a couple of kids, but is barely making ends meet and is ashamed of this fact. He goes a few months every year without income and is filled with insecurity about his finances almost all the time. He’s too stubborn to take a full‑time job and instead of admitting he might be wrong about his approach to life, he angrily tweets about how stupid everyone is working in traditional jobs. This is all complicated by ongoing health issues which limit his energy and sometimes leave him semi‑bedridden for weeks at a time. The negative future version of me is financially insecure, does not have a predictable income, and is cynical and stubborn.

[Me: I did a similar exercise before taking the leap. It is deeply uncomfortable and I don’t think I’d be ok writing it down for the world to see. I give Paul tons of credit for his vulnerability]

I could become “negative me” by doing the following: spending time with negative and cynical people, not finding supportive friends, not staying open to all kinds of paid work (including full‑time employment), obsessing over divisive media and politics, working on things I resent, and not being honest about my own motivations. Inverting helps you identify traps that could derail your efforts to keep your journey alive.

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.

[Me: Take this seriously]

Trail magic — find your fellow travelers

You need models, inspiration and friends for this journey

The person I was most drawn to, Seth Godin, had built a life around creativity, generosity, and helping others. I didn’t know if I could be like Godin, but knowing that someone like him existed made me believe that kind of path was possible. 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.

It’s no surprise then that many people who take unconventional paths often grew up surrounded by people in their families who also took unconventional paths.

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. Nine times out of ten these people will be enthusiastic about connecting with you because they are still searching for people to learn from on their own journey.

[Me: This person for me was Paul and my mutual friend Khe Hy. Khe is also referenced in the book and I encourage fellow travelers to read his writing about transitions and what to expect.]

However, this kind of digital inspiration is often only helpful at the beginning of the journey. Ultimately, you need to find people who are open to a deeper friendship and willing to spend meaningful time together.

Some seemed to know everything about me without needing to ask. 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.

[Me: I’ve had this experience as well and hope I can be that person for 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. 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.”

[Me: That Cowen quote is pinned to my Notion dashboard. It is a core value in what I try to do. I see education as an enabler. There’s nothing like the excitement when a kid discovers they can do something they never have before. The 3 examples that stand out in my experience is seeing my eldest son’s reaction when he discovered he can swim, when he first rode a bike, and when he recovered from being stranded on a zipline without panicking. You could split an atom with the energy released from this empowerment. Once you see it, you just want to keep unlocking it. Self-belief is the cheapest source of capital on the planet]

You are creative

In the early 1900s, professor and writer Bertrand Russell noted that “any person who visits the Universities of the Western world is liable to be struck by the fact that the intelligent young of the present day are cynical to a far greater extent than was the case formerly.” He argued that developing a cynical stance was necessary in a world in which much of what authorities and leaders claim directly contrasts with what is true. The cure for such cynicism, he said, would “only come when intellectuals can find a career that embodies their creative impulses.”

Take A Step

So maybe I’ve convinced you that it’s worth sharing, but you don’t want to launch a social media brand, start writing online, or publish a book. That’s fine too. You can start small or do something in your local community. Host a dinner party in your city or town, start a book club, share a poem or essay you’ve written with a couple of close friends, or even join a local art class. It doesn’t matter how you start but that you start. Once people enter this new, creative mode, they realize that they’ve been holding back a part of themselves for most of their lives. Deep inside, we all have a desire to engage with the world in creative ways and don’t worry, I’m here to cheer you on.

You have to take actions

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.”

[Me: It’s a good time to remember — the rules are all made up. Nobody is in charge]

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. We are ultimately the ones that determine our fate, and without expressing agency, we struggle to be free.

[Me: Are you truly exercising this alleged freedom that you have?]

A Roadmap

Reflect

For me creating a daily reminder of four priorities that mattered to me and revisiting the leadership principles I aspired to in grad school helped me see that the gap between what I claimed to care about and how I was living was larger than I wanted.

Figure out what you have to offer

In our desire to be successful, we forget to notice how we are having an impact on others. One of the easiest ways to begin this exploration is to send a message to a few close friends, asking them, “when have you seen me at my best self?” Their responses may surprise you and, perhaps, delight you. We all have stories about who we think we are and why we must be that way but often, others have a better perspective on what makes us stand out.

Go Make A Friend Venture out of your existing bubble and reach out to someone who has taken an interesting path. Ask them how they got started, what motivates them, and how they think about navigating their life. Most people are much more enthusiastic about sharing what they’ve learned in their lives than we expect. To embrace the pathless path, you need friends and all you need at the start is one person. Over time, designing your work in a way that will help you naturally “find the others,” can be one of the most rewarding things of being on the pathless path and one of the most valuable things you can do in life.

[Me: This advice is something both me and my wife advocate to people who feel stuck. Get connected. Lead by sharing first.]

Go Make Something Paint a picture, or host a cooking class for your friends. It doesn’t matter what you do, but the sooner you figure out a way to create and share with the world, the faster you’ll be able to move closer to finding the activities you want to continue doing.

Give generously Generosity is not only an amount of money, it is a skill we need to practice. It is a way of orienting towards the world that will help you start to understand your own definition of “enough,” grapple with your hidden money scripts, and enable you to decouple your belief that security and money are perfectly linked.

[Me: Beautifully said]

Grappling With Retirement and Money Scripts

It would be unnatural to read this book and not think about the role money plays on the Pathless Path. Ways about thinking about money and retirement are stretched throughout the book since it’s an ever-present constraint on any journey. There are specific headings devoted to the topic towards the end of the book as well.

This section captures Paul’s reflections that stood out for me. Let’s start with retirement.

Waiting for Retirement

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

While the traditional idea of retirement is motivating for many, others might benefit from thinking about it from the perspective of the pathless path. 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.

Why mini-retirements are important

The best approach I’ve found for figuring out how I want to live is Tim Ferriss’ idea of “mini‑retirements”.

He designed his own mini‑retirements, trips of “one to six months” where he would test out living in different ways.

While designing these breaks into his life he asked himself three questions: How do your decisions change if retirement isn’t an option? What if you could use a mini‑retirement to sample your future plans now? Is it really necessary to commit fully to work to live like a millionaire?

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.

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?”

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.

For me, 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.

[Me: The idea of mini-retirements sounds risky until you recognize that their purpose is actually to use experiments to test what you really want. Again, without using the word “miswanting”, Paul hones in on a pervasive theme. Many people’s desires are not their own, but they think they are. It’s difficult to tell the difference if your environment doesn’t change. When your routines don’t change. When you don’t meet new people. Mini-retirements are actually just an example of “take the effort to discover what your true must-haves and nice-to-haves are”.]

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.

Links to My Retirement posts

I’ve written about retirement stuff in:

The “R” Word

Follow Up To The “R” Word

Let’s widen the scope from retirement to money in general.

Reimagine Money

The secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours. — Amos Tversky

[Me: This quote is resonant and is a reason I advocate for living below your means. An idea I’m into is how having slack in your system is the antidote to “Moloch” (the god of unhealthy competition — see: Putting Moloch To Rest) But this quote also reminds me of a lesson I learned early in my trading career: “If you win every day you’re not maximizing”. In the context of investing, this quote addresses the tension between increasing your expected value and cutting risk which is costly. A simple example, would be a poorly capitalized trader buying something that's worth $5 for $4 but then selling it for $4.25. I’d say they made a $1 winning trade, followed by a $.75 cent losing trade. Yes they earned $.25 profit but they didn’t maximize.

There can be good reasons for this. Like I said, they were poorly capitalized so survival might require them to effectively “spend $.75” to cut risk. But the analogy is useful. How does your own risk-aversion cost you? Is the cost in proportion to the benefit?

A personal example: My scarcity mindset, which was an adaptive mindset when I was younger and broke and had no connections was a useful tool to protect my downside, while likely costing me some upside. As your downside (basic material needs) become more assured the scarcity mindset becomes an overly expensive hedge. To be all option trader about it, the mindset used to be a 25 delta put but it’s now a 5 delta put. It’s just that I’m still paying the price of a 25 delta put.]

Back to Paul...

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.

William Whyte, wrote about this shift in his book The Organization Man, published in 1956. He shared a snippet of writing from a young man typical of the era:

“What distinguishes the comfortable young men of today from the uncomfortable young men of the last hundred years…is that for once the younger generation is not in revolt against anything…We don’t want to rebel against our elders. The organizations that these young people joined offered predictable incomes and, most of all, predictable lives. Whyte saw this as a dramatic shift from the past because these organizations offered something that previous generations did not have, a safe haven from the real world, noting that “come graduation, they do not go outside to a hostile world; they transfer.”

Because I belong to the third generation of this tradition, I didn’t have people around me to tell me how life without a paycheck would feel. When I left my job, I expected that working on my own would be challenging, but I did not expect my entire relationship to money and its role in my life to change.

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.” 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.

With money coming in and a lower cost of living, my financial insecurity decreased, leading to a chain reaction in my understanding of work. If I wasn’t working for money, why was I working? When we work full‑time, employers are paying for our dedication and commitment to the job as a central part of our life. 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.

Many people I talk to are convinced that the formula for living on their own terms is saving up enough money. I wish they knew what I know: 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.” 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.

[Me: These bold sections remind us that life is risk. Are you really living? The pathless path is like a workout for your living muscles which have atrophied]

Combining What We’ve Learned

A Better Way of Defining Success

The better way is what I call 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.

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

If we can learn to coexist with our financial insecurities, we can turn them into a secondary concern. This opens you up to the real secret: the opportunities of the pathless path are infinite too.

[Me: The upside of improving our relationship with money is enormous because of all the secondary and downstream effects! So important.

It reminds me of a conversation I had with a friend recently. He also lives in the exceedingly expensive Bay Area. He said when he used to meet a teacher he would think: “oh you made a bad choice”. But now, with the benefit of maturity, he thinks “oh you have a healthy relationship with money”. I burst out into desperate and overwhelming laughter. It was a lightning bolt.]

Permission To Take A Step

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

It’s a shift from the mindset that work sucks towards the idea that you can design a life around liking work. I didn’t realize how profound this shift is until I sat down to write this book.

If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you. — Gospel of Thomas

Quote I’ll wrap with:

Nothing has been more consistent than the reality that most people want to engage with the world and to be useful. Despite many people thinking that their ideal life would be living out the rest of their life on a beach, when given the option of following that path, few people take it. Author Sebastian Junger, in his book about soldiers who had returned from war, found a similar thing. Despite dealing with post‑traumatic stress disorder, many of the soldiers wanted to return to dangerous warzones. Why? Because at war, they felt part of something, deeply connected to the men and women they were serving with. Junger reflected, “humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.” Junger argues that “modern society has perfected the art of making people not feel necessary.” The need to feel useful is a powerful one. This is the hidden upside of the pathless path and a reason why finding work that aligns with what matters to you and makes you feel useful is so important. When you find the conversations you want to take part in and the work you want to keep doing, you start to feel necessary and the whole world opens up.

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