The Pathless Path | Alessandro Desantis

At its core, The Pathless Path is the journey of Paul Millerd as he quits his dreadful job as a McKinsey consultant in New York, turns into a content creator, starts traveling around the world, and eventually moves to Taipei with his wife.

Paul uses his story to make an argument for stepping off the “default path” (the one that requires people to go to school, get a degree, get a boring corporate job, get married, buy a house, etc.) and embracing the “pathless path” (which, to sum it up, is the one where you only do things that make you feel alive).

I’ve been curious about this book for a while, but I’ve avoided it because I’m immediately skeptical of anyone who goes on some life-changing journey and then turns around and starts making a living by telling others how to take that same journey. It’s just a much more sophisticated form of the Ponzi scheme (cue course creators selling courses about how to become a course creator selling courses about how to become a course creator).

With this book specifically, I was terrified to open it and find some sort of get-rich-while-working-from-the-beach checklist, which would have left me screaming to get my money back. Luckily, that’s not the case—in fact, Paul acknowledges that there’s no defined process for walking the pathless path (it wouldn’t be pathless otherwise, would it?), and that it often goes up and down and sideways and round and round and down some more. Life is seasonal, after all.

Still, I found myself rolling my eyes constantly while reading it.

My main issue with Paul’s point is that, even though he acknowledges the non-linearity of the pathless path, he still seems to have a very fixed perspective on what the result of walking the path should look like. The fundamental notion of the book is that, if you are not obscenely in love with your job, you are wasting your life, and you should redirect your energies toward finding and doing a job you love.

I find this problematic for two reasons.

The first reason is that this is a very privileged point of view. Paul is extremely lucky to make a living out of his passion for writing, a profession very well known for exhibiting winner-take-most characteristics. Research suggests that this is true in most creative fields: even when skill differences are relatively small, a tiny portion of creators reaps up the majority of the rewards. In other words, “making the jump” requires significant skill, good timing, extreme financial discipline, a decent dose of luck, and ideally plenty of savings so you have time to figure it all out before going broke.

Instead, The Pathless Path is filled with the pervasive notion that all it takes is enough willpower, and you, too, can move to a tropical country and live the life of your dreams. Unfortunately, this is simply not true. You may very well starve yourself by doing the work of your life, at which point it doesn’t matter how much you love writing or painting or whatever it is you like spending your days doing. No one escapes Maslow.

To some, this might feel inspirational and empowering. To me, it’s just one more way of shifting responsibility from the system to the individual, and making people feel inadequate for not living up to a very subjective standard—so much for the “pathless” path.

This brings me to the second problem I found in Paul’s argument.

I find the entire idea that you have to love your job to be extremely reductive of the richness of human experience. In fact, while it’s hard to trace it back to its roots, I suspect that the idea that you have to love your job was born from the same mind that came up with the idea that your company is a big family: it’s the card your boss pulls when they want you to feel really warm and fuzzy about putting in 60-hour/weeks without paying you for it.

While it’s certainly nice when you can make it happen, loving your job is not nearly as important as not hating your job. In this sense, work is like money: being rich doesn’t make you happy, but being poor will definitely make you miserable. Once you reach the point of diminishing returns, you’re more than welcome to keep exploring your options, but you should also consider that maybe, just maybe, you should start giving your fucks to something or someone else.

While these are my objections to the book’s arguments, I also found it to be lacking in structure. Throughout the book, Paul keeps jumping from one story to another, sometimes struggling to make a clear point. When he does make a point, he repeats it ad nauseam, and his typical argument goes “I did X, therefore Y” or “Person X that I admire did/says Y, therefore Z”, with very little analytical rigor.

Don’t get me wrong—it’s a fun, inspirational read, but that’s all there is to it. Once you strip it of the anecdotes, the quotes, and the repetition, I would put this squarely in the “could have been a blog post” category. It’s a leaf book, not a branch book.

Truth be told, reading The Pathless Path made me a little angry, and I want to apologize because anger is never a good place to write from.

It made me angry because, while I am incredibly lucky to be doing (mostly) what I love and getting (mostly) paid good money for it, I have several people in my life for whom that is not the case. People who would love nothing more than to live through their favorite form of art or science, and yet exist in a market that cannot support them—not because they lack skill or conviction or willpower, but because our dreams are our own and the economy is everyone’s.

Most of these people haven’t given up, but they have made a responsible, grown-up decision to keep doing what they love without expecting it to turn into a full-time profession. To go to these people and tell them that they’re doing some kind of disservice to themselves and to the world would be cruel, unfair, and false, because they live lives made of loving friends and bad jokes and immense generosity and all other manners of important things, and what else is there to living?

Conversely, I’ve also had people in my life who were adamant on walking the pathless path, all consequences be damned, and all they did was cause a lot of pain to the people they loved and who loved them back. They were so focused on the destination that they forgot about all the people they abandoned along the way.

Despite all of the above, I would still recommend reading The Pathless Path, especially if you’re unfamiliar with some of the concepts. It will broaden your ideas about how life can be lived, and help you understand which path is the right one.

Just make sure you’re not swapping one path for another.

Highlights

Researchers Dorthe Berntsen and David Rubin study what they call “life scripts,” which they describe as “culturally shared expectations as to the order and timing of life events in a prototypical life course.”⁠
prestige is “a powerful magnet that warps even your beliefs about what you enjoy.”⁠6
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.
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.
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.”⁠
In Aristotle’s own words, “we are not-at-leisure in order to be-at-leisure.”
According to Taggart, living in a world dominated by total work undermines the “playful contemplation concerned with our asking, pondering and answering the most basic questions of existence.”⁠
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.⁠
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.
With wonder, the need to cope becomes less important and the discomfort on the current path becomes more noticeable.
“If it is right, it happens—The main thing is not to hurry. Nothing good gets away.”⁠
Often we don’t notice our drift into a state of low‑grade anxiety until we step away from what causes it,
We all have fixed points that we aim toward in our lives. Homeownership is one of the most popular, but others include paying for children’s college expenses, becoming an executive or partner, founding a company, or reaching a certain net worth.
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.
If the default path is the story of the industrial world, then the pathless path is the natural story for a digital‑native world in which nothing can stop us from finding others who share our desires, ideas, and questions.
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.
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.
No money is worth it if it undermines your desire to stay on the journey.
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.
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.
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.⁠
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.
Ultimately, figuring out what to do with freedom once we have it is one of the biggest challenges of the pathless path.
“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.”⁠
We are ultimately the ones who determine our fate, and without expressing agency, we struggle to be free.
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.”