Making, Not Finding, Your Way: Review of The Pathless Path by Paul Millerd

Castles in the Sky #4

Last month on Twitter, several people I consider smart, unconventional thinkers recommended a new book by an author I had never heard of.

The descriptions and blurbs I could find were somewhat vague, like this one from Amazon, “The Pathless Path is about finding yourself in the wrong life, and the real work of figuring out how to live.” It seemed like the book was about picking the right career, a topic about which my own job search and years of teaching at a university have made me an armchair expert. 

The vagueness of the marketing materials, uniform positivity of the reviews, and my familiarity with the subject matter made me explicitly skeptical that I would enjoy the book, and subtly skeptical that I could learn anything from the book at all.

Luckily, I was completely wrong. The author pulls a lovely bait and switch: it’s not really a book about careers at all. 

Through summary, review, context, and memoir, I want to make the case that the book, The Pathless Path by Paul Millerd, is immensely important because of both its content and its context. On its own, the book has a wide range of interesting and useful ideas to offer concerning careers, the nature of work, leisure, society, and how we measure our lives. Beyond that, the book serves as the most recent interest development in a centuries long debate about how to decide what to do with your life.

Approaching the Pathless Path

This is from the Amazon blurb: "The Pathless Path is about finding yourself in the wrong life, and the real work of figuring out how to live." As I mentioned before, the blurb and reviews made it difficult to discern exactly what the book is about, or at least what you would walk away with. 

I was pretty prejudiced going into reading the book. I lived in Beijing from 2010-2013. Already back then, there was an explosion of people, mostly millennials, who had what I called lemonade lifestyles. An implosion in the job market, a dearth of affordable credit for houses, and an average student loan debt higher than ever before meant that the safe, cushy, lifelong jobs people had expected to come after college since the baby boom just did not exist any more. 

Many smart, capable young people felt they had been sold a bill of goods about what college would get them. College graduates raised on the internet looked around, collectively said, "fuck this," and got jobs they could work from anywhere. They had taken the lemons handed to them by the 2008 financial crisis, inescapable student debt, and inevitability of boomeranging back to mom and dad's house, and turned it into the lemonade of digital nomadhood. They then lived off their laptops doing online or gig work, usually in places their western currency went really far, like South America, East Asia, or Eastern Europe. 

Automation, remote work, consistent travel, entrepreneurship, being a brand, prioritizing experiences over possessions, grinding (sometimes), prioritizing mental health over the grind (other times). There were a lot of trends that emerged form this movement which persist to today. Tim Ferriss, with his book The Four Hour Work-Week, was one of the first high profile people to advocate for a lot of the things digital nomads aimed for. The tagline for that book was, "The 4-Hour Workweek is a new way of solving a very old problem: just how can we work to live and prevent our lives from being all about work?" (Sound familiar?) 

The 4-Hour Workweek was a great book, and Tim Ferriss is someone I still follow and look up to. On his podcast, his most ubiquitous media property, Tim Ferriss starts most (or maybe all episodes) by saying something close to, "welcome to the Tim Ferriss show, where it is my job to deconstruct world class performers to tease out the routines, habits etc. that you can apply to your own life." 

From his podcast and some parts of his books, I think that Tim Ferriss is a rather deep thinker and thoughtful person generally. However, I do begrudge Tim Ferriss one thing: he is arguably one of the most famous and successful proponents of "hacks." In the purest sense, a hack is a way of being more efficient, but what it usually comes across as is a shortcut. (For example, Tim Ferriss famously became a world champion kickboxer, despite not knowing how to kickbox, because he exploited a loophole in the rules.) 

He is one of the leaders of a subculture--emblematic of our larger culture--where people are obsessed with hacks in the name of productivity. If you are not sure what I mean, take a look at his book Tools of Titans, a great book to be sure, but it is primarily a list of lists. First, it is a list of the names of over 100 people he has interviewed, and for each person he has a short list of takeaways from that interview. Don't get me wrong, this book is excellent, probably the best of it's kind. However, it distills lifetimes of often pathologically intense focus into a list of “tricks” someone might try out. This excessive, cut-and-dry focus on hacks bothers me for two reasons. 

The first reason this bothers me is that books like this, which promise to share the hacks of the very most successful people, usually focus on the top 1%, or rather the top .001% most successful people in their given field, and what they do differently from others. (For example, a sampling of names from Tools of Titans: Brene Brown, Jack Dorsey, Malcolm Gladwell, Arnold Schwarzenegger.) There is a lot of important context and cumulative growth missing from these accounts. 

The vast majority of people would do much better to copy the habits that the top 10% most successful people have in common with each other, rather than the habits that the top .01% of people do differently than everyone else. Analogously, it would be like people obsessing over the fact that Michael Jordan used to stick his tongue out when he dunked, rather than the prodigious amount of hours he spent practicing or his inhuman will to win, both traits he shared with an enormous number of his contemporary NBA athletes. 

The second reason that the focus on hacks bothers me is that it has shown how lucrative teaching hacks is, and therefore created a tremendous number of copycats. In the last 15 years or so, there has been an explosion in the number of people writing about productivity. Books, videos, and podcasts abound with hacks specifically and with habits and routines more broadly, which are lesser offenders although a similar crime. 

Many of these books are great, but many are also artless: lacking grace, meaning, or depth. They are essentially selling shortcuts. A huge number of people are spending a lot of time thinking about "how" to do the things that make up life more efficiently or quickly, because that sells better than people talking about "what" to with one's life or, even more profoundly, "why" to do it. 

The saddest part is that some of the most famous people for whom hacks are just part of their repertoire, like Tim Ferriss or people similar to him, have extremely nuanced takes on other topics, and a whole lot of depth. Using Tim Ferriss as an example, I found his TED talk about suicide and his fear-setting exercise tremendously moving. 

That being said, the people want hacks! When you search "Tim Ferriss" on YouTube and order the results by most views, the TED talk is the fifth most popular video. The first is a clip from his old TV show where a chess grandmaster hustles a chess hustler, but the second most watched video is, "How To Peel Hard-Boiled Eggs Without Peeling." Peeling eggs! 

Bemoaning our hack-happy society may seem quixotic. However, I'm not the only person who has noticed it. Who’s to blame? Tim Ferriss? Not really. Society at large? Maybe, but that seems lazy are not particularly useful. The main point of this detour is to inventory the baggage with which I arrived at The Pathless Path. 

I have an unconventional career. Even within my career, my success and work is measured in unconventional ways. Being a millennial, I am the age where I and everyone I know have spent the last 15 years finding and building careers. Beyond that, I often work with people trying to find a job or start a business. I have read a lot in the last decade about career paths, nontraditional career paths, and making the most out of life. Trust me when I say that there is a lot more media out there of the "list of hacks" than there is about thoughtful re-examination of the ideas you hold closest. 

The Anti-Hack

Because of the baggage I brought to the book, I anticipated a cheap list of hacks. I held disdain for the shape which I assumed this book would take, full of straightforward, gimmicky productivity shortcuts. Paradoxically, as I skimmed the book and began reading, I could feel myself judging the book precisely because the opposite was happening: I was getting drawn into the story and as I became more engrossed, it was getting harder to figure out what the hacks would be, and when the actionable takeaways would start. 

Over the course of reading the book, Paul Millerd won me over. The Pathless Path is actually a mindset book. Many books claim to be mindset books which can show you how to think in new ways, but they are really just name drops and hacks, or worse, memoirs. Using a mountain climbing metaphor, many books that try to position themselves similarly to the Pathless Path merely talk about how to plant a flag at the summit, and very few ever talk about how to climb the mountain. Almost nobody talks about how to find the right gear and guide. They are usually journey retrospectives, where they try to fit everything into a neat, linear narrative. This technique might make the story inspiring, but it almost guarantees the lessons are not useful. 

Extending the metaphor of the mountain climbing memoir, Millerd touches on planting the flag, explains some of his climb, and gives a good accounting of gear and guide. But most importantly, he zooms out and writes about the macro forces which pulled his gaze across the horizon to the mountain looming in the distance, and how he methodically and incrementally made his way toward and up it. He does not just tell you what his mindset is at the time of climbing, but how he evolved from someone who never looked up from his path, to someone who daydreamed of hills, to someone who climbs mountains. 

What I really liked about this book is that it is the opposite of what I anticipated: it has zero hacks or to-do lists. Paradoxically, it has a more methodical, applied method toward reinventing yourself and your career than I have read about anywhere else. On the one hand, reading the book is a somewhat circuitous, wandering experience. It's hard to get exactly at what this book is about, even well over halfway through it. 

That's not to say that epiphanies do not abound throughout the book, they do. It's just not clear until late in the book how everything comes together. On the other hand, once it does come together, it's a revelation: so obvious that you wonder how you looked at it differently before. In this way, the book is an anti-hack. 

Something that made me laugh is that, well into writing this essay about the book, I still thought The Pathless Path was a stupid title. But again, Millerd has lead me on a journey, where through writing about the book, I get it. The Pathless Path is about going somewhere, but not following anything. This is how the book is an “anti-hack” book. 

A hack promises a straightforward shortcut, where you can omit some work on the way to achieving some goal, saving you time and challenging nothing. This book does the opposite. You wander along through the author's life story, then some anecdotes, quotes, and syntheses of other people's ideas, unsure of where exactly you are going. Then suddenly (for me at least), you "get it." You have grown. Your worldview has changed. Something has been illuminated, but not because someone gave it to you in a straightforward, easy-to-digest way. You have been lead on a journey. 

As opposed to a hack, where you take a shortcut to get something you knew you wanted, you finish this book and you have taken the long way to a completely new place. After three paragraphs of explaining how this book is the anti-hack, I still have a nagging voice that says, "bring this idea together, synthesize it in a concrete way." The people who would wait for that concrete synthesis to decide whether or not to read this book are probably the people who should read the book the most, so I resist the urge. 

Prototyping Your Passion

In addition to The Pathless Path being an antidote to hacks, an anti-hack if you will, there is another important piece of context. The Pathless Path adds a lot to the decades-long debate between those that say, “follow your passion,” and those who advise to be more practical and just find something that pays well. There are a range of disparate ideas I want to draw on to make this point.

In the year 1645, Japanese swordsman Miyamoto Musashi wrote in The Book of Five Rings, “from one thing, know ten thousand.” Ostensibly, he meant that deep study of a particular discipline would give you insight into many other disciplines. This quote is appropriate because The Book of Five Rings was written specifically about how one might be an effective swordsman in post-feudal Japan (400 years ago), but The Book of Five Rings is still read in hundreds of languages around the world for its lessons on conflict, strategy, deliberate practice, and many more currently relevant topics.  

Important to the idea of deep study Musashi advocated was practice. Someone engaged in deep study had both the knowledge and hands-on experience to become a master of a topic. Often, the combination of deep knowledge and practice evokes thoughts of an expert or master, someone who “practices one kick ten thousand times” as Bruce Lee once said. However, the key point is not that you have to do something ten thousand times to be good at it or understand it, but rather that doing something at all gives you real-time feedback for your theoretical knowledge. The more time you spend testing the theoretical knowledge, the more data you are collecting. 

Expanding this idea, there is an argument to be made that if you are not trying to develop deep, narrow expertise, that you can still accumulate an immense amount of practical wisdom by learning about a range of theoretical frameworks and routinely testing that knowledge in the real world. This is often referred to as first principles thinking. It is an old idea that remains popular, and while there are drawbacks to thinking this way exclusively (which I hope to write about later), it is a good idea to think this way more often than not. 

First principles thinking and deliberate practice are central to The Pathless Path. 

As I alluded to earlier, I'm a millennial. I do not know what career advice has been like for most of time, but for most of my time on Earth in the Western world, conventional advice has been to "follow your passion." One thing I heard a lot as a kid was, "find a job you love, and you'll never work a day in your life." Teachers, guidance counselors, parents and others pay a lot of lip service to sorting children into the activities and subjects that they most enjoy, and what is lucrative or practical is usually not addressed until adulthood (if ever at all). 

As they often do, these ideas have degenerated into memes. The idea of following your passion has lost a lot of context, and in the last five years or so there has been a lot of pushback against it. The first I remember seeing pushback was around 2013-2014 when I saw Mike Rowe's video, "Why You Should Never Follow Your Passion." Mike Rowe is advocating people find high-paying blue collar trades, but this idea has made its way into universities and corporate spaces too, as when Scott Galloway said in 2020, "follow your passion, what utter bullshit." 

Part of the reason that these critiques are spreading and gaining popularity is that the advice to “follow your passion” so devoid of context that it is almost always impractical. It seems "woo woo." It seems reckless and unserious. Mostly, it seems cavalier and naive. What The Pathless Path does extremely well is take "follow your passion" and reframe it from something reckless, unserious, cavalier, and naive into something careful, thoughtful, methodical, and contemplative. 

The way that Millerd does this is by advocating first principles thinking and deliberate practice. 

The way that Millerd uses first principles thinking is really exquisite. He draws on history, philosophy, and sociology, quoting many great thinkers of history in their own voice. The main takeaway is that our current conception of work and its place in our life is not only not the way it’s always been, but is relatively new on the scale of human history, and even now there are many different ways to think about work. 

(Trying to -re-synthesize the way he synthesizes it would only lead to a poor imitation, but a few of the ideas he touches on that I found particularly salient are Max Weber’s idea of traditionalist work, Erich Fromm’s idea of positive freedom, Dr. Tal Ben-shahar’s idea of the arrival fallacy, and finally Thomas J. Bevan’s Misery Tax. Of particular interest to me was the fact that the Greek translation of work is “not-at-leisure,” and that Aristotle once described work by saying that “we are not-at-leisure in order to be at-leisure,” meaning leisure was apparently a really important part of one’s life at that time.) 

Often there is an assumption that "follow your passion," should end with "to a lucrative career," insinuating that the only place worth following your passion would be to a new job. The Pathless Path challenges this assumption through first principles thinking about what a job or career is and how it fits into your life. Then, after a fundamental reframe of where a passion might lead, and why we might want or not want that, The Pathless Path goes on to detail a methodical means of finding out what your passion is, and whether or not you actually want to follow it. 

Millerd suggests not to up-and-leave leave your current job to follow your passion. Unsteady, you prototype what your life might be like after following your passion. Do small test runs of what might happen after you make the big change. I have shortened this idea to prototype your passion to get the point across. 

In Chapter 6, First Steps, the first section is “Prototype Your Leap.” Millerd says:

“My story is not one of courage, but of pragmatic and safe experiments, experiences, and questioning over several years. This approach, one of prototyping a change, is not only a better way to think about taking bold leaps but is quote common across many people’s stories [of doing so included in the book].”

I will guess–based on the Twitter users I saw endorsing The Pathless Path–that most readers of Millerd envisioned would know the term prototype from entrepreneurship. Inc.com defines prototypes as “working models of entrepreneurial ideas for new products.” This is particularly popular in the tech world as outlined in books like The Lean Startup by Eric Ries. 

By advocating people to prototype their passion, Millerd is practicing both first principles thinking and deliberate practice. Millerd is advocating using first principles thinking by taking this business idea and applying it to potential lifestyles. Going back one step further, this idea is actually another application of first principles thinking: someone got the idea to use the scientific method in generating new products and business lines. 

Millerd is advocating deliberate practice by not just taking a “leap of faith,” but prototyping your lifestyle and actually practicing what you want to do before you make any massive and possibly irrevocable changes to your current lifestyle. Earlier in the discussion of success literature and hacks I wrote, “The vast majority of people would do much better to copy the habits that the top 10% most successful people have in common with each other, rather than the habits that the top .01% of people do differently than everyone else.”

This is essentially why I think this book is so valuable. I imagined Millerd would agree based on what he says about prototyping in one of my favorite paragraphs in the book: 

“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.” 

The real stories he writes about being those which contain the commonalities between the top 10% of people who have effectively made the life change most successfully, rather than those focusing on the most outrageous and inspiring outliers of the top 0.01%. 

Final Thoughts and Recommendation

Clearly, I’m a fan of the book and I recommend it unambiguously. It’s hard to say that “everyone should read” any book, but when I start to narrow down who the ideal audience would be for The Pathless Path, it’s a pretty wide net. Anyone who has any lingering or persistent dissatisfaction with their career should read this book. Anyone who is not sure about what to do next should read this book. If you have people in your life in the previous two categories, you should read this book. 

It’s a rare book in that it is tangentially about careers and being more focused and productive, but unlike almost every other book I have read about these topics, I finished this one and felt better about myself and my career. That’s not to say there are not areas of dissatisfaction or things  I would change, but The Pathless Path gave me a new lens with which to view my work and life, rather than similarly marketed books which give a set of principles or a to-do lists which are invariably unattainable. 

I generally consider books on three criteria, being how I felt when reading them, how I felt when finished, and what I take away from the book. For the first and third, I give the book top marks. 

The book’s style conversational and very engaging. Millerd is accomplished in a conventional sense but also has had some difficulties. Even when talking about his accomplishments however, he does not do so in a way that feels like he is bragging. He also excellently balances personal stories, synthesizing others’ ideas, and the connective tissue. 

There are a lot of takeaways from the book; the lessons I’ve outlined here are just a start. 

The Pathless Path was a cerebral and thought-provoking book. As I got closer and closer to the end, I took longer and longer breaks in reading to daydream and think about my work and life. At the end of the book, there is a short summary of the main points, but I was so thoroughly on my journey of implementing what I learned that I almost did not read the summary because I did not feel I needed it. 

The fact that I had been so thoroughly impacted during the course of reading meant that by the end of the book, I had already crossed the major threshold of change that usually comes with finishing the book. So even though the “completion” of the book did not really impact me, I feel like this is not something I would hold against it. 

In conclusion, I would like to share one of my favorite quotes by Dolly Parton: “Find out who you are and do it on purpose.” Millerd also uses this quote in the book. If you are also someone for whom Dolly’s advice seems like a good idea, then you should probably pick up or download a copy of The Pathless Path.