The Pathless Path (Part I)

*People who are experiencing a nagging, persistent sense of lack or dissatisfaction with the current trajectory of their lives, and who want to take a peek at the map of someone who's traveled just a little bit further ahead.

*Corporate wage slaves who want to make a change in their lives, but are unsure of what that might look like, what to expect if they do, their chances of success after they take the leap, and how the important people in their lives might feel about it.

*Artists and professionals in all fields who have ever been through a crisis of meaning and who consistently struggle to separate their sense of self-worth from what they "do" or what they produce.

*Literally anyone and everyone who believes that reality is negotiable and that the future doesn't necessarily have to look like the present.

"I want to see people live the lives they are capable of, not just the ones they think they are allowed to live."

-Paul Millerd, The Pathless Path

The chances of a perfect life path being successfully scripted for you by someone else are precisely zero. We exist in a community of others, but individually, we are completely alone and our lives are up to us.

More than that, we have the opportunity - the ability - to curate our own reality every moment, and by definition, no one can do this for us. We think that the meaning of life is "out there" and that we have to find out what it is. When in reality, it is Life that asks us the questions, and how we live is our answer.

In the same way, Paul Millerd doesn't have any answers. There are no hacks or step-by-step formulas in this book, no mandatory reading lists, and no milestones you have to hit in order to live a meaningful life.

Instead, The Pathless Path is about the invisible scripts that shepherd us into prescribed modes of living and being in the world; it's about freedom and creativity; it's about money, meaning, and work; and it's about being fearlessly, unapologetically yourself, in a world that shouts back, "You can't do that!"

It's also about going somewhere, but not following anything. Getting lost, and finding yourself. Leaving, but never arriving.

The book itself kind of meanders between Paul's personal story of leaving his high-profile career in search of work that matters, the history of work in our society, the meaning of money, entrepreneurship, alternative careers and lifestyles, and more. There's a Table of Contents, sure, but it doesn't tell you any more about the experience of reading the book than a map of Athens would tell you about ambling through the ruins of the Acropolis.

Mostly, though, it's about looking at the ladder you're climbing right now and asking yourself whether it's actually leaning against the right building. So if you've ever woken up in the wrong life (and who hasn't?), this is one of the books you may want to read next.

The default path - doing what everyone is doing, living the same day, week, month, and year that everyone else is living over and over again - used to work for most people. But this future that we're building together is not a default future. We have so many more options and opportunities - possibilities for our lives that we can explore and take to their logical conclusions. The default path is dying away, and we have to come to terms with our own freedom and what we want to do with it.

You might ask why, if the default path is so horrible, so many people choose to walk along it. The answer is that it's not so bad. It's actually pretty comfortable, it doesn't come with a whole lot of surprises, and you may even find moments of happiness - or something close to it - that allows you to shut out the awareness that there's so much more of you being left unexpressed.

I mean, here you are, the universe's most spectacular creation, and you're just kinda getting by. Living a "good enough" life, surviving day to day, coasting through a default world you never made.

The Pathless Path is Paul Millerd's answer to the question of what makes meaningful work and what we might aspire to in our lives. But you and I can never be Paul Millerd. His life is taken. You can only be yourself, and I can only be myself. The pathless path is narrow, wide enough for only one person. You.

#1: Heed the Call to Adventure

“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 trust that an uncertain future is not a problem to be solved."

Milan Kundera said that we live everything as it comes, without warning, like an actor going on cold. Life is fired at us point-blank, and we feel that this is true, so we tend to fall into comfortable, "safe" patterns of living because the uncertainty of life is, by definition, unsafe.

What Paul Millerd calls the default path is the "safest" route through life. It might get you to the end of your life without any major turbulence - less danger, less social disapproval, less financial insecurity, etc. - but it's no way to live. Not for a significant number of us, anyway.

The default path is synonymous with the "script" that society tries to convince us is the only way in which we can allow our lives to play out. It's just "what's done" by respectable people, and it involves such relatively uncontroversial things as pleasing your teachers and your parents all the way through school, jamming your days and evenings with extracurriculars and resume stuffers that look good on a university application, making it into that prestigious college and getting your $200,000 degree (that you'll be paying for until you're 40), getting an "okay" job, putting your head down for the next 40 years, and then dying with that gold watch they slap on you in honor of all your years of "faithful service."

Before I go on, I should clear something up: There's nothing necessarily "wrong" with the default path. Not everyone who travels along that road is a mindless sheep, forfeiting their existence for the false freedom of a 2-day weekend and a 401K. For some perfectly fulfilling, profitable careers, you need to go to college. I went to university for philosophy, and I don't regret it one bit. In fact, I'm using my degree right now as I'm writing this breakdown!

But there's more to life than internal memos, meetings, and team-building exercises. Such things may populate the "real world" you've been living in until now, but you don't have to live in it. You can embrace the pathless path and live consciously, and intentionally, like an actor who has read further ahead in the script than the other players and who's ready to give the greatest performance of their life.

The writer and mythologist Joseph Campbell has done a great deal to shape my thinking about the pathless path as well. The default path may have worked for Paul Millerd's parents (and mine too), but we're living in the future now, and 'we must be willing to let go of the life we planned so as to have the life that is waiting for us,' as Campbell has written. He also said the following, which idea will become even more clear in Key Idea #3 below:

“If you can see your path laid out in front of you step by step, you know it's not your path. Your own path you make with every step you take. That's why it's your path.”

Joseph Campbell is also largely responsible for moving the concept of the "hero's journey" into the public consciousness. Famously, George Lucas read Campbell's book, The Hero with a Thousand Faces more than 100 times, and you can see elements of the hero's journey all throughout Star Wars - and throughout virtually every other great story ever told.

The Hero starts off in what's called the Ordinary World, where he lives relatively unconsciously in a world he never made. In Star Wars, this would be Luke Skywalker living a normal life on his home planet. For the rest of us, it's the default path where we're told to quiet down, conform, and not make any sudden moves.

But then comes the Call to Adventure - usually in the form of a crisis - that shocks the hero into full wakefulness and makes him conscious of the existence of the Extraordinary World, beyond the confines of his original existence. I won't rehash the entire plot of Star Wars, but all the elements of the hero's journey are present there, as they are in our own lives as well.

Right now, most people are living in the Ordinary World. The default path is the water that they're swimming in, and they can't see a better way to live, because everyone around them is swimming in the same water.

Suddenly, however, a Mentor appears and shows us the way to the brighter, more vivid, more meaningful life that's available to us if we would only break free from the Ordinary World and step out into the Extraordinary World. For Luke Skywalker, that Mentor was Obi-Wan Kenobi, but in The Pathless Path, it's Paul Millerd.

Now, obviously, the Extraordinary World is not a safe place. You will run into Enemies; you will experience Trials; you may even face your own All is Lost Moment when the extreme challenges and difficulties of your new life make you long to return to the comforts of the Ordinary World.

This is normal. It's also one of the only guarantees you will ever receive along the pathless path. Literally by definition, the route is uncertain, your chances of success variable, and subject to the vicissitudes of fortune. But is the purpose of your one and only life just to coast by? Just to arrive at the moment of your death completely unscathed? Or is the purpose of your life to be fully alive?

The default path will almost always be there for you to return to if you wish (more on this later), but right now, today, the pathless path is calling. Our destination is uncertain, and even our direction can change dramatically, but we make the path by walking. And as Nietzsche advised, do not ask whither it leads; go along it.

#2: A Healthy Beggar is Happier Than an Ailing King

“So much of my identity had been connected with being a high achiever. Straight A's. Dean's List. McKinsey. MIT. When I was sick, I would have traded every last credential for a single day of feeling okay."

The world will ask you who you are. And if you don't know, the world will tell you. That was actually Carl Jung - I'm not quite as wise as he was - but what he said is painfully true. I've seen it happen too many times to mention, and it never hurts me any less.

I look around and I see people shortchanging themselves in all kinds of ways, abdicating their power to form their own identities, and compressing themselves to fit inside the predetermined molds that society says are the only ones available. This is the default path. In Paul's case, it's part of what made him physically ill, and he's not alone. You are not alone.

The fact is that it feels good to tell people that you're in the Honors program at such and such big-name college. People treat you differently when you walk around in corporate prison clothes (ties have always looked like nooses to me), and most people know about the addictive social approval found in the smiles and visible satisfaction of strangers when they learn that you've accomplished some impressive...thing. Most people would do anything to avoid the "other" look. You know the look I mean.

I've been on the receiving end of both: the looks of admiration and approval when I step out of my sports car holding a thick book in my hands, the looks of derision when I used to show up to work as a nighttime security guard at a city hospital. But the funny thing is that in that both situations and at all times in my life, I was always just...me!

The parts of me that made me a valuable person, someone entitled to a feeling of self-worth and positive regard, were with me the whole time, no matter what job I had or what kind of car I drove.

Every single person in the world is infinitely deserving of basic human dignity and respect, and that is your inalienable right so long as you exist on this great green earth. The default path, however, conspires to make you forget that fact, and it literally made Paul Millerd sick.

The philosopher Arthur Schopenhauer said that "a happy beggar is happier than an ailing king," and that's certainly been the experience of people like Paul and myself. He and I would likely give up everything we have just to hold onto our health and vitality, and the tradeoffs that the default path asks us to make in this area are tradeoffs we're not willing to make. The downside is just too horrible, and the "upside" is hardly worth having.

Again, there's nothing wrong with driving a fancy car or being a CEO. Just like there's nothing wrong with spending the day pursuing your artistic ambitions, or working a decent, honorable job, even one that pays $10/hour or less. There are as many good lives available as there are people to live them.

In his book, Die With Zero, investor Bill Perkins discusses the delicate balance between three of your most important resources in life: your time, your money, and your health. His observation is that all three resources rarely show up in one person's life all at the same time.

When you're young, you may have to give up some time (and even some health) in order to have more money later. It's just that it makes zero sense to spend all your time, and deplete all your health, just to buy it all back in the future when you find yourself at death's door.

Any kind of health challenge is typically accompanied by a radical refocusing on what's really important in life. When you're sick, the only thing you want is to get better, and there's no compensation package or investment plan that can make you forget that you used to be young, healthy, and free.

The sooner you realize this the better: the healthy person wants ten thousand things; the sick person wants just one.

#3: The Adjacent Possible

“‘Are those the only two options?’ I asked. 'Yes,' he replied. 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."

Picture everyone you know, all standing together inside the same room. They don't seem too uncomfortable - they're even making light conversation, and some even look like they're enjoying themselves - but you start to notice that they all kind of look the same, talk in the same way, believe the same things, etc.

After a while, you realize that you're the only person in that whole room who actually notices a door leading somewhere else.

In fact, now you begin to think that it's strange that no one else is even looking for a way out. They're just kind of there, existing. The fact is that they have either never wondered about the possibility of any other kind of existence, or they do in fact know that there's a door that leads to a different room (or to places unknown) but they're afraid to make their exit.

Now imagine that somehow, you manage to overcome any anxiety you may feel about leaving that room with everyone you know inside and you actually do push through that door. What's on the other side?

You have just stepped into the adjacent possible and taken your first step along the pathless path. That second room you've entered will look completely different from any second room that I would enter, or Paul Millerd would enter, or virtually anyone else on the planet. But, in all cases, there exist a multitude of different doors, each leading out into a series of different rooms - different lives - and you know what?

The whole world is like that. We live in a universe of infinite possibilities, and almost like a video game, when you make one choice, open one door, the room you've just left fades into nothingness again and you must confront the newest set of choices you've just made possible for your life. We are always collapsing our own wave functions with each and every choice we make.

If you think that's a terrifying prospect, well that's because it absolutely is! The existentialist philosopher Jean-Paul Sartre said that human beings are condemned to be free, and the "terror of freedom" is kind of what he meant.

In life, so many of the doors we've just closed will be locked behind us. We move forward into our uncertain futures, with no guarantee that we can ever return to where we started from. And it's so much easier to just stay in that first room, to say, "You know what, this is good enough. It's easier. I think I'll just stay here with everyone else."

Worse still, we learn from the people around us that the first room "isn't so bad." We learn that it's easier not to have a deeper conversation with oneself. Paul Millerd felt the same way, of course. He started off in that first room with the rest of us! And he overstayed his welcome there because:

“I was too afraid to have a deeper conversation with myself. The kind that might pull me towards a different kind of life."

#4: Does It Hurt Enough?

“Given sufficient coping strategies, people will be willing to tolerate consistent levels of misery for long stretches of time. Is there anything that can override this?

In my conversations with people who have made changes in their life, one thing seems to work reliably: wonder. Wonder is the state of being open to the world, its beauty, and potential possibilities. With wonder, the need to cope becomes less important and the discomfort on the current path becomes more noticeable."

There's an old story about a dog that was sitting on a nail but refused to move. Visitors to the house would ask the owner why the dog never made any attempt to move, and he would just shrug his shoulders and say, "I guess it just doesn't hurt enough to move."

In the same way, it's because of their various coping strategies that people can stay on the default path for as long as they often do. It just doesn't hurt enough to move, not when they can self-medicate with alcohol, Netflix, and social media. With drugs and the daily news. Or worse.

Compensatory strategies can even include numbing ourselves with things like high salaries and attractive benefits packages. It's like Nassim Taleb says: the three most addictive things in the world are heroin, carbohydrates, and a monthly salary. Different prisons look wildly different to different people, and we submit to varied punishments by staying on the default path, but it's all the same.

Now, is escape possible? I'm sincerely asking the question. I don't have a ready-made answer prepared for you. No one does.

But like Millerd says in the quote above, one thing works reliably well to induce people to make changes in their lives, and that one thing is wonder.

Wonder goes by many different names. Jiddu Krishnamurti calls it the immeasurable. Joseph Campbell says that it's found in the Extraordinary World. Colin Wilson believes that the Outsiders of society are able to access it more easily than most people.

But what all these experiences have in common is the deep, visceral recognition that the Real World is right here, that Life is now, and that the Future will not wait.

Wonder - Reality, Awe, Paradise, Essence - is the true nature of the universe, and its purpose is to shock you into full wakefulness and to wake you up to the actual possibilities for your one and only life.

Like many people before me, I've had this experience literally thousands of times, and often, it was because of one particular sentence in a great book. I could choose any number of a hundred of the best examples, but I'll pick this line from Fahrenheit 451, by Ray Bradbury, and shake you by the shoulders with it:

“Stuff your eyes with wonder, he said, live as if you'd drop dead in ten seconds. See the world. It's more fantastic than any dream made or paid for in factories.”

#5: Conduct Mini-Experiments

“As I’ve lived in different places around the world and focused on different kinds of work, I've created mini-experiments that help me learn more about how I want to live my life.

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?'"

The life you're living now is a rough draft. It's an experiment, a hypothesis, an unfinished screenplay you're in the process of revising over time.

In the end, your daily existence could look wildly different than it does now - and you simply don't know the exact shape your life could take in the future if you tried on more different lives.

In the extremely influential book, The Four-Hour Workweek, lifestyle experimenter Tim Ferriss asks why we postpone retirement, putting it off until the end of our lives instead of more evenly distributing it throughout our lives while we still have an improved capacity to enjoy it. Why indeed?

One of the most dangerous elements of the default path is that it obscures the potential reality of our unlived lives. We imagine that our current path is the only one that's possible, so we never even think to try anything else. Or even imagine that we could try anything else!

I know of virtually no more efficient path to painful, devastating regret than never trying to punch through your own prison walls every so often and see whether or not they are, in fact, made of paper instead of stone.

Try new things! Experiment! Test! Test! Test!

Paul Millerd has the right idea here. While there's some value in "burning the boats" and going all-in on your creative passions, you can help make experimentation feel a lot less scary by formulating an exit strategy. Or rather, a return strategy. Save up some living expenses. Keep in touch with former clients and business associates. Stay up to date on the knowledge and best practices of your current field. But try something else too.

To avoid going broke at the casino, only bet what you can afford to lose. The same applies when it comes to running lifestyle experiments, so it's important to survive to test again.

Define what the "worst case scenario" means for you in terms of your experiment, and do everything possible to prevent that. As long as you gain something from your experiment, and you live to tell the tale, there's likely no irreversible downside to you taking that leap.

The way I always try to set up my own life is to give myself many ways to win and no way to lose. For example, building a personal brand online. Most of the tools I use are free, and there are no gatekeepers in my way telling me that I can't write book breakdowns or tweets, or LinkedIn posts.

Writing on Medium.com is free, I get paid for it, people sign up to my email list after reading my articles, I become a better writer by writing every day, and I make connections with other writers...where's the downside? There is none! I literally cannot lose. The time I spend writing is enjoyable, too, so nothing is wasted. Many ways to win, and no way to lose.

The only way I can lose is by doing nothing. By not experimenting. Because regret is real. Crushing dissatisfaction with the way you've spent your one chance at life is one of the most horrible punishments imaginable, and it's self-inflicted. So take a page or two from Paul's playbook and start running some lifestyle experiments:

“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."

I’ve been taking detailed notes from every single book I’ve ever read since 2014, and they’re all here on my Patreon for just $1.

They’re updated monthly (sometimes twice a month), and by supporting me on Patreon you’ll also be able to keep up with everything I’m reading and learning, and get my best notes, takeaways, and summaries from every book that I finish.

More Patreon rewards are available as well, like being mentioned by name in all my YouTube videos, Patron-only discounts, special offers, and more.

Reply

or to participate.