This Book is For:

*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.

Key Ideas:

#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!

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 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."

Book Notes:

“This is the pathless path. Where the journey leads is to the deepest truth in you.”

-Ram Dass

“My restlessness was easy to hide because my path was filled with impressive names and achievements, and when you're on such a path, no one asks, 'Why are you doing this?'"

“I was able to shift away from a life built on getting ahead and towards one focused on coming alive.”

“The hardest questions often don’t have answers.”

“The best option available for my parents was the default path. This worked remarkably well for them, which is what made leaving it so damn hard. I know how much they sacrificed so that I would have better career opportunities.

However, what they really gave me was so much more than the ability to succeed in school and work. It was space to dream, take risks, and be able to explore more possibilities for my life."

"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

“The modern world offers an abundance of paths. In one sense this is great. It's the result of an industrial system and resulting prosperity that has created opportunities for people around the world.

However, the proliferation of paths presents a challenge. With so many options it can be tempting to pick a path that offers certainty rather than doing the harder work of figuring out what we really want."

“The desire for security and the feeling of insecurity are the same thing.”

-Alan Watts

“The house became not only a second home, but a gathering space for friends, family, and acquaintances. The door was open to everyone as long as they agreed to eat my grandfather's food. He never talked about his childhood, but according to his siblings, after their mother died, he was sent to live on a farm with his uncle.

Sometime around fourth grade, he stopped going to school so that he could start working with his uncle. He didn't have a childhood filled with love and support. He chose to deal with it by trying to do better for his children and grandchildren and he succeeded.

Like many of my cousins, we feel like we won the lottery growing up with a family like ours, where thanks to my grandfather we had access to a magical world filled with love, laughter, and possibility.

Sitting in the house in Arizona, I knew I was about to lose him, one of the most important people in my life. Those few days were filled with tears and overwhelming emotion, but also with beauty and a profound sense of meaning. The proof of his life's work was in front of us. He had succeeded in creating a world better than the one he had grown up in. It was clear to me in those moments that family, love, and relationships were the most important things in the world.

Despite this clarity, I struggled to remain present in the days before he passed. I couldn't stop thinking about work. What if my colleagues needed me? To settle my anxiety, I drove to a local cafe and checked my email. Everything was fine. A colleague messaged me, 'What are you doing!? Go back with your family, we got you!' I smiled and closed my laptop.

Driving back from the cafe, I was angry at myself. Why had I been so worried about work, something that was clearly not important? As I walked back into my grandfather's house, the house was silent. He was taking his final breaths. Had I nearly missed this moment because of some silly emails? I joined hands with my family, said a prayer, and left my worries aside for the next few days."

“Many self-employed people are surprised to find that once they no longer have to work for anyone else, they still have a manager in their head."

“The Ancient Greek translation for 'work' was literally 'not-at-leisure.' In Aristotle's own words, 'we are not-at-leisure' in order to be-at-leisure.' Now, this is flipped. 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.'"

"In stepping away from my temporary identity as a freelance consultant, I let myself fully lean into what I would later call the pathless path. As I wandered Asia, my mind exploded with possibility. If it was possible to work from a laptop in Bali, what else had I not yet considered? My imagination was open, and I was ready to see where it might take me."

“We must let go of the life we have planned, so as to accept the one that is waiting for us."

-Joseph Campbell

"The incommunicable trees begin to persuade us to live with them, and quit our life of solemn trifles."

-Ralph Waldo Emerson

"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

“Why not take the usual 20-30-year retirement and redistribute it throughout life instead of saving it all for the end?"

-Tim Ferriss

“No amount of money can buy the peace of mind that comes with finding a path that you want to stay on.”

“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.”

“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.”

"Whatever takes us to our edge, to our outer limits, leads us to the heart of life's mystery, and there we find faith."

-Sharon Salzberg

“The fact that our next steps are unknown to us is exactly the point.”

“This is not just a lesson for individuals to unlearn, but one for society to unlearn, and we'll be amazed at the energy that's liberated when we do."

-Paul Graham

"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."

-The Gospel of Thomas

"Whereas money today embodies the principle, 'More for me is less for you,' in a gift economy, more for you is also more for me because those who have, give to those who need it. Gifts cement the mystical realization of participation in something greater than oneself which, yet, is not separate from oneself. The axioms of rational self-interest change because the self has expanded to include something of the other."

-Charles Eisenstein

“It’s the generous person who is the wealthiest.”

-Charles Eisenstein

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.

The headline, “Quits to Live on a Sailboat” seems more impressive and is easier to talk about than “Couple Slowly and Purposefully Tests Out a Life Transition while Aggressively Saving Money Over Five Years.” As a result, we hear fewer of the real stories, most of which include some kind of prototyping.

“There are many ways to make money, and when an obvious path emerges, there is often a more interesting path not showing itself."

“After reading this book, you should no longer be able to look at your current path and think, 'This is definitely the only way.' Instead, I hope you are able to shift to a place where you know that you have more freedom than you think, and your path can become something you choose again every day."

Excellent Sheep, by William Deresiewicz:

If you left university with just a degree and a pile of debt, you were robbed. Somewhere along the way, colleges and universities drifted away from being centers of higher learning and loci of self-discovery, into being commercialized profit centers, and students themselves became "customers," or, worst of all, commodities.

William Deresiewicz is a former Yale professor with a deep, infectious passion for higher education, which is self-evident throughout Excellent Sheep and which leaps from every paragraph. He cares; he cares so much, and his distress at the decline of educational standards in the United States and elsewhere is shared by myself and a multitude of other educators who know what school can really do.

Universities today often force students to choose between learning and success; the straight path to riches and prestige is prized above real education, real introspection, real meaning, and the creation of one's own real life.

Higher education should be about the cultivation of our highest potentialities as individuals, and it should prepare us to meet life with optimism, intelligence, dignity, and care. In the final analysis, whether our educational system helps or hinders this process is up to us.

Sample Quotes from the Book:

“The purpose of college, to put all this another way, is to turn adolescents into adults. You needn’t go to school for that, but if you’re going to be there anyway, then that’s the most important thing to get accomplished. That is the true education: accept no substitutes.

The idea that we should take the first four years of young adulthood and devote them to career preparation alone, neglecting every other part of life, is nothing short of an obscenity.

If that’s what people had you do, then you were robbed. And if you find yourself to be the same person at the end of college as you were at the beginning – the same beliefs, the same values, the same desires, the same goals for the same reasons – then you did it wrong. Go back and do it again.”

“The system manufactures students who are smart and talented and driven, yes, but also anxious, timid, and lost, with little intellectual curiosity and a stunted sense of purpose: trapped in a bubble of privilege, heading meekly in the same direction, great at what they’re doing but with no idea why they’re doing it.”

“This is your shot. This is your chance to become, not the person that you want to be, not the person you’ve decided that you’re going to be, but the person that you never could have dreamed of being.”

Read the Full Breakdown: Excellent Sheep, by William Deresiewicz

The Outsider, by Colin Wilson:

If ordinary life usually seems a bit...well, may be because the way most human beings live their lives can be compared to an extraordinarily powerful jet airplane flying on only one engine. That's Colin Wilson's basic contention in The Outsider, where he outlines his fundamentally optimistic philosophy of New Existentialism.

Wilson exploded onto the literary scene with this book, which came out in 1956 to massive acclaim. It's never been out of print since then, and it's been translated into more than thirty languages. What's more, is that he was only 24 years old when he wrote it! After publishing The Outsider, he went on to write more than 100 books, including six others which, along with The Outsider, comprise the "Outsider Cycle," a fuller representation of the ideas first proposed here.

I just happened upon this book one time – I had never heard of it before – and thought it looked interesting, given that he references philosophers and writers I enjoyed reading, such as Kierkegaard, Camus, Dostoyevsky, etc. I had no idea that it would completely change my life forever after and would radically alter how I lived out each day of my one and only life.

Sample Quotes from the Book:

“Normally man’s mind is composed only of a consciousness of his immediate needs, which is to say that this consciousness at any moment can be defined as his awareness of his own power to satisfy those needs. He thinks in terms of what he intends to do in half an hour's time, a day's time, a month's time, and no more.

He never asks himself: What are the limits of my powers? In a sense, he is like a man who has a fortune in the bank, who never asks himself, How much money have I got?, but only, Have I enough for a pound of cheese, for a new tie? etc."

“Man’s moments of freedom tend to come under crisis or challenge, and when things are going well, he tends to allow his grip on life to slacken.”

“Let us summarize our conclusions briefly: The Outsider wants to cease to be an Outsider. He wants to be 'balanced.' He would like to achieve a vividness of sense-perception (Lawrence, Van Gogh, Hemingway). He would also like to understand the human soul and its workings (Barbusse and Mitya Karamazov). He would like to escape triviality forever, and be 'possessed' by a Will to Power, to more life.

Above all, he would like to know how to express himself, because that is the means by which he can get to know himself and his unknown possibilities. Every Outsider tragedy we have studied so far has been a tragedy of self-expression."

Read the Full Breakdown: The Outsider, by Colin Wilson

The Second Mountain, by David Brooks:

What if you spent your whole life climbing the ladder to success, only to find that it was leaning against the wrong building?

In this spectacular and damn-near urgent book, political and cultural commentator David Brooks uses a different vertical metaphor - two mountains and a valley - to explore the devastating effects of our culture's unrestrained individualism, the dark night of the soul that's waiting for us when we discover that we've been sold a bill of goods, and what a full life of what he calls "moral joy" might look like.

The "first mountain" represents the relentless pursuit of success and achievement that's possessed the mind of the Western world for so long.

When you climb the first mountain, what you're really cultivating are the "résumé virtues" - the skills and talents you bring to the marketplace. On the second mountain, it's all about the "eulogy virtues" - what they talk about at your funeral.

The Second Mountain is an intensely personal book and one that will stop you cold in dozens of places as you pause to ponder the profundity of what others have discovered about the true aims of life. It can't just be about the self.

A real human life - a committed, relational life - is lived on the second mountain, with others. For others. Brooks explains how we got this all mixed up, and he also offers numerous practical and lofty ideas about how we can restore balance to our inner lives.

He's also fond of quoting George Eliot, author of Middlemarch, although my favorite quote of hers doesn't appear in The Second Mountain. It, however, nicely summarizes Brooks's central idea, and it goes something like this:

"What are we here for if not to make life a little less difficult for one another?"

Sample Quotes from the Book:

“The lesson is that the things we had thought were most important - achievement, affirmation, intelligence - are actually less important, and the things we had undervalued - heart and soul - are actually most important."

"It turns out that freedom isn't an ocean you want to spend your life in. Freedom is a river you want to get across so you can plant yourself on the other side - and fully commit to something."

“Life is not a solitary journey. It is building a home together. It is a process of being formed by attachments and then forming attachments in turn. It is a great chain of generations passing down gifts to one another."

Read the Full Breakdown: The Second Mountain, by David Brooks

Put Your Ass Where Your Heart Wants to Be, by Steven Pressfield:

“When we say, ‘Put your ass where your heart wants to be,’ we mean station your physical body in the spot where your dream-work will and must happen. Want to write? Sit down at the keyboard. Wanna paint? Step up before the easel. Dance? Get your butt into the rehearsal studio. Dumb and obvious as it sounds, tremendous power lies in this simple physical action.

-Steven Pressfield, Put Your Ass Where Your Heart Wants to Be

Steven Pressfield is essentially the patron saint of artists and creatives everywhere, and this book is a wonderful exhortation toward greater commitment to one’s chosen craft, and a call to go “all-in” on your creative endeavors.

Pressfield just gets it; he’s been there, and after one hell of his own hero’s journey, he’s returned to show us how to “make it” as well. If you're still stuck in the depths of fear, self-doubt, procrastination, and perfectionism, however, then this book could really help you.

At the core level, it’s a book about giving up everything for a dream, and about why doing something “crazy” like that can make life worth living, at least for a certain type of person. You might be that type of person, and if you are, you’re going to feel seen while reading this book as well.

Throughout the book, he blends the practical and the metaphysical in a way that’s just…awesome…and if you believe that you have something great inside of you but aren’t sure how to access it, then you need to read this book.

Sample Quotes from the Book:

“You too have a body of work. It exists inside you, on the Plane of Potentiality. Are you a writer? This body of work exists, like books on a bookshelf. Close your eyes. You can see them.

Are you a musician? These works exist like albums, like concerts, like performances. Listen with your inner ear. You can hear them.

These bodies of work exist as alternative futures. They are that which can be…and should be…and want to be. But they are not that which is guaranteed to be.”

“Can we put our ass where our heart wants to be if we’ve got a family, a job, a mortgage? Yes. The Muse does not count hours. She counts commitment. It is possible to be one hundred percent committed ten percent of the time. The goddess understands.”

“What would it be like to train as a quarterback beside Tom Brady? How hard would we have to work to practice alongside Steph Curry? How would we feel submitting our manuscript to Maxwell Perkins, who edited Hemingway and Scott Fitzgerald? When we say, ‘Put your ass,’ we mean put it at the highest possible level.”

Read the Full Breakdown: Put Your Ass Where Your Heart Wants to Be, by Steven Pressfield

The View from the Opposition:

No one's ideas are beyond questioning. In this section, I argue the case for the opposition and raise some points you might wish to evaluate for yourself while reading this book.

#1: If You Don't Have Money, You're Not Allowed to Have an Opinion

The world is rapidly being separated into the have-nots and the have-yachts, and money is an important element of power in today's world. Not just political power, but personal power as well, not to mention personal safety.

Getting as rich as possible and increasing your spending power is one of the best ways I know of to protect yourself from abuses of power, random life events, and even the necessity of following the default path at all. Having FU money is the best defense against the default path, and if you don't have it, you're in danger of having a boss for the rest of your life.

Obviously, money isn't everything. Having money isn't even necessarily in direct opposition to walking the pathless path - the internet has made it so much easier and more possible to make a fantastic living by doing what you love. But don't run away from money. Don't think that money is somehow "evil" or that being poor makes you a good person. Money is a mirror that can show you who you are, and it's actually the lack of money that is the root of all evil.

The fact is that if you have more, you can give more, and I honestly don't believe you can help very many people if you're poor yourself. You may be a wonderful person at heart, but millions of children under the age of 5 starve to death each year because you and I don't have the money to help feed them.

#2: It Would Never Work in a Hinge Bio

I can only speak for men, but I think you'll find that most women don't want to date a man who's less successful than they are, and it's the roughly 2% of men who are both over six feet tall and earn more than $100,000 a year that have access to most of the dating opportunities.

This is the real world we live in, and although it would be great if women could see "the real you" or know that you're a "good guy" who just wants to make her happy, the reality is that she will probably leave you for the 6"4 investment banker with the Porsche and the seaside villa.  

To be clear, I'm absolutely not saying that all women are like this, or even that most women are like this, but a large number of them are, and I'd just like to see most men put "pathless wanderer" in their dating profiles and watch how many matches they get. Probably not that many.

This is obviously fairly controversial - and hey, if you do find someone who's willing to take the $75,000 a year reduction in household income while you go out and "find your passion," I'll be the first to congratulate you - but your dating life will almost literally always be easier if you have money and maintain some sort of higher status in society.  

Full Disclosure: I may also be doing that thing people do where they know that they aren't motivated by money but believe that everyone else is (while everyone else is thinking the exact same thing), but I don't think so.

Go out and make some money. Gain a few hundred thousand followers. Lease a McClaren. Then report back and tell me if you're still single by this time next year.

"The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time and still retain the ability to function.”
-F. Scott Fitzgerald

Questions to Stimulate Your Thinking:

The quality of your questions determines the quality of your life. That's also how you get the absolute most out of any book that you decide to read:

You ask great questions the whole time - as though the book was on trial for its life.

Here in this section are a few questions that can help guide and stimulate your thinking, but try to come up with your own additional questions, especially if you decide to read this book the whole way through...

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

#2: "Are you on the default path now? How comfortable are you? Are you tempted to leave? Motivated to make a change? What might that look like?"

#3: "When was the last time you heeded a Call to Adventure - some event, conversation with a friend, or inner stirring that caused you to reevaluate your current path?"

#4: "How much money do you need to maintain your current lifestyle? Can that be reduced? By how much? By reducing your fixed expenses, can you open some space for greater freedom and possibility in your life?"

#5: "Of all the things you currently spend money on, how many of those things did you buy in order to show other people how successful you are? Did they even notice? And if they did notice, do you think they're still thinking about you when you're not there?"

#6: "Have you ever tried eliminating something from your life that you believed you could never live without? What would that be? Can you experiment with eliminating it from your life for 30 days?"

#7: "If you embarked on the pathless path tomorrow, what could be some benefits of doing so? What would success, or even a partially successful attempt look like for you?"

#8: "If you don't make a change, what might be the cost of inaction? In 3 months? In 3 years? At the end of your life?"

#9: "Who are you? No really, who are you? If you asked yourself this question five times in a row and kept asking 'Who are you beneath that?' who would you be then?"

#10: "Are you willing to let go of the life you have planned in order to make room for the life that's waiting for you?"

"Judge a man by his questions, rather than by his answers."

Action Steps:

So you've finished reading. What do you do now?

Reading for pleasure is great, and I wholeheartedly support it. However, I am intensely practical when I'm reading for a particular purpose. I want a result. I want to take what I've learned and apply it to my one and only life to make it better!

Because that's really what the Great Books all say. They all say: "You must change your life!" So here, below, are some suggestions for how you can apply the wisdom found in this breakdown to improve your actual life.

Please commit to taking massive action on this immediately! Acting on what you've learned here today will also help you solidify it in your long-term memory. So there's a double benefit! Let's begin...

#1: Make the Path by Walking

I recognize the absurdity of outlining Action Steps for following the pathless path, but bear with me here.

In fact, I'm going to direct you to Kyle Kowalski's excellent book summary of The Pathless Path, where he takes Paul's suggestions from Chapter 10 about how you can embrace the spirit of the pathless path and puts them into this handy infographic:

"The path to success is to take massive, determined action."
-Tony Robbins

About the Author:

Paul is a self-described "curious human" who spent more than fifteen years trying to play a game that he wasn't designed to win. Walking away from the "default path" of success, including a good paycheck, impressive credentials, and unlimited career options, he starts from scratch, creating space in his life.  Over a number of years, he discovers a different way of thinking about the role of work in our lives, which he calls The Pathless Path.  This path doesn't make him rich with money but does make him wildly rich in time, connections, and meaning.

Additional Resources: | Main Website

Boundless by Paul Millerd | Newsletter

Boundless Reads | Suggested Reading

The Pathless Path Podcast | Listen Now

Book Summary: The Pathless Path | Sloww

Making, Not Finding, Your Way | Charlie Becker

This Book on Amazon:

The Pathless Path, by Paul Millerd

If You Liked This Book:

The Second Mountain, by David Brooks

Excellent Sheep, by William Deresiewicz

Put Your Ass Where Your Heart Wants to Be, by Steven Pressfield

The Outsider, by Colin Wilson

The Psychology of Money, by Morgan Housel

Die With Zero, by Bill Perkins

Bullshit Jobs, by David Graeber

Hell Yeah or No, by Derek Sivers

The Four-Hour Workweek, by Tim Ferriss

Vagabonding, by Rolf Potts