PART ONE: THE DEFAULT PATH
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 trusting that an uncertain future is not a problem to be solved. Ultimately, it’s a new story for thinking about finding a path in life.
By default path, I mean a series of decisions and accomplishments needed to be seen as a successful adult. These vary by country, but in the United States, we refer to this as the “American Dream,” which means a life centered around a good job, owning a home, and having a family. Researchers Dorthe Berntsen and David Rubin study what they call “life scripts,” which they describe as “culturally shared expectations as to the order and timing of life events in a prototypical life course.” Their research found remarkable consistency across countries with regard to the events that people expect to occur in their lives. Most of these moments occur before the age of 35: graduating from school, getting a job, falling in love, and getting married. This means that for many people, expectations of life are centered around a small number of positive events that occur while we are young. Much of the rest of our lives remains unscripted and when people face inevitable setbacks, they are left without instructions on how to think or feel. While very few young people expect to have one job or career, most still rely on the logic of the default path and assume they need to have everything sorted out before the age of 25. This limits the ideas of what we see as possible and many, including me, internalize the “worldly wisdom” that John Maynard Keynes once pointed out, “that it is better for reputation to fail conventionally than to succeed unconventionally.
I was physically present but detached. Rather than participating in meetings as a good team member, I observed them as a visiting anthropologist. I saw my colleagues with new eyes. Are they happy? What kind of pain or challenges are they dealing with? Is this how they want to be spending their time? Once you ask these questions there is no going back. Not because of the contradictions in other people’s lives, but because it makes it di"cult to live in contradiction in your own life.
Our tendency to glorify and simplify stories of people quitting their jobs convinces far too many people that this move is only possible for uniquely courageous people. 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 quite common across many people’s stories.
By experimenting with different ways of showing up in the world and making small, deliberate changes, we can open ourselves up to the unexpected opportunities, possibilities, and connections that might tell us what comes next.
I suggest people take a more active approach to find what I call “path experts.” These are people ahead of you on a path you might be interested in taking. It could be someone who left a job like yours or someone exploring a way of living that fascinates you. Nine times out of ten these people will be enthusiastic about connecting with you because they are still searching for people to learn from on their own journey.
Although people considering the option of leaving the default path can list hundreds of things that might go wrong, they struggle to talk about the fears behind those risks. In hundreds of conversations with people, I’ve found that these fears fall into one of the following five areas:
Success: “What if I’m not good enough?”
Money: “What happens if I go broke?”
Health: “What if I get sick?”
Belonging: “Will I still be loved?”
Happiness: “What if I am not happy?”
During my first few years of self‑employment, these fears overwhelmed me, but Tim Ferriss’ “fear setting” reflection exercise helped me reframe them and see fear in a completely new way. The exercise has six steps. The first four are straightforward:
Write down the change you are making.
List the worst possible outcomes.
Identify actions you could take to mitigate those outcomes.
List some steps or actions you might take to get back to where you are today.
However, some fear‑related problems cannot be solved. The authors of Designing Your Life offer a helpful reframe, calling these issues “gravity problems” which are part of life “…but, like gravity, it’s not a problem that can be solved.” This phrase helps me sit with my discomfort when I worry about my health. Due to lingering health issues, I sometimes go long stretches with very little energy. Reminding myself that this is a fact of life, like gravity, helps me accept the uncertainties of life and the pathless path. The final two questions of Ferriss’ exercise are the most powerful:
What could be some benefits of an attempt or partial success?
What is the cost of inaction in three months, 12 months, and in a few years?
This shifts the focus from the future, which is inherently uncertain, to the present, which helps us see our tendency to overestimate future costs and underestimate costs related to the status quo.
PART TWO: THE PATHLESS PATH
I started to wonder if taking a break from work and embracing states of non‑doing were e#ective ways to improve life satisfaction. I was starting to realize a profound and positive shift in how I was thinking about my life and wondered if others had similar results. I reached out to people who had taken such breaks and found that most people credited these breaks from work as one of the most important things in helping them see the possibilities in their life. I also started to notice that many of the shifts that people experienced were somewhat predictable. Four stand out: First, people become aware of their own suffering. Often we don’t notice our drift into a state of low‑grade anxiety until we step away from what causes it, as I noticed the first day after I quit my job and realized I was burned out.
Second, curiosity re‑emerges. When people have time, they try new activities, revisit old hobbies, explore childhood curiosities, and start volunteering and connecting with people in their community. Edward, a friend and a doctor who has taken several sabbaticals, reflected that “new ideas often pop up and old topics of interest float back into my consciousness. I fond myself writing notes and thinking more freely. This is the creative process, liberated by the neocortex now that the mind isn’t wholly occupied by the strain of everyday sustenance, the rat race, and the grind.
Third, people often desire to continue their “non‑work” journey.
Fourth, people write.
While the traditional idea of retirement is motivating for many, others might benefit from thinking about it from the perspective of the pathless path. On the pathless path, retirement is neither a destination nor a financial calculation, but a continuation of a life well-lived. This shifts attention from focusing on saving for the future to understanding how you want to live in the present. The best approach I’ve found for figuring out how I want to live is Tim Ferriss’ idea of “mini‑retirements,” which he introduced in his book, The Four‑Hour Workweek. He got the idea after realizing that he disliked typical vacations where you pack as much as possible into one or two weeks. After getting burned out on a short trip, he asked himself the question, “Why not take the usual 20–30‑year retirement and redistribute it throughout life instead of saving it all for the end?” With this mindset, he designed his own mini‑retirements, trips of “one to six months” where he would test out living in different ways. He described these as an “anti‑vacation” and “though it can be relaxing, the mini‑retirement is not an escape from your life but a reexamination of it—the creation of a blank slate.” While designing these breaks into his life he asked himself three questions:
How do your decisions change if retirement isn’t an option?
What if you could use a mini‑retirement to sample your future plans now?
Is it really necessary to commit fully to work to live like a millionaire?
The power of these questions is that they force you to be creative and experimental. For me, I’ve found that this makes life more fun. 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 spirit of the mini‑retirement is not about escaping work. It is about testing different circumstances to see if you want to double down on them or change directions.
It was incredibly painful for me to realize that if I truly cared about living in a di#erent way, I might need to leave the business world. The journey towards the pathless path often starts at this moment, with a willingness to investigate your disappointment and to wonder if there is a better way of defining success. The better way is what I call the “second chapter of success” in which you shift your mindset from what you lack to what you have to o#er, from ambition to aspiration, and from hoping that joy will result from a specific outcome to experiencing it as a byproduct of your journey.
The concept of prestige is shifting quickly. As our connections to local communities have broken down, we are paying more attention than ever to people who are successful in the traditional sense, through money, status, or fame. But below this %ashy surface, many people are seeking out smaller and quieter communities where they can earn prestige in a way that suits their lives.
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. It’s a shift from the mindset that work sucks towards the idea that you can design a life around liking work.
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.
My friend Jonny Miller argues that “human existence is an infinitely unfolding process of remembering, forgetting, and remembering again.” To thrive on the pathless path, we must ignore the shiny objects and distractions and strip away the stories that are not our own to remember who we are. One of the biggest concerns people have when they talk to me about quitting their job is how to make money. That is certainly important, but a more interesting path is possible if you start with what brought you alive in the past. Injecting the energy from these pursuits can lead you in a different direction and can help you figure out what to work on while taking the first steps toward creating a life you truly enjoy.
Figuring out who you want to serve is an important element of the pathless path. On the default path, your job often provides recognition and praise. When you are on your own, without a specific job or colleagues, you may miss that kind of support. This is why it’s so important to know what kind of people you want to work with and who you want to serve.
Maybe I’ve convinced you that you are creative and that you should ignore the voices that tell you that you should not create. However, you still have some concerns, especially if you are thinking about sharing online. Isn’t the internet just filled with scammers or people that want attention? The fact that those people make you feel uneasy is a good sign. Because the people creating those posts probably don’t feel uneasy at all. And this is why I want to urge you to consider sharing with the world. You care. You want to do things in good faith. You want to help people, to listen, and connect with others who share your passions. This doesn’t mean you need to build an audience or a business, but what might emerge if you dare to share your writing, painting, dancing, crafts, or other acts of creativity with others? What friends might you meet? What opportunities could you pursue? What communities could you join?
Even if you do decide that sharing your real work with the world is worthwhile, it’s nearly impossible to overcome the sense that you may embarrass yourself. Here it’s helpful to remember the “spirit of the fool” and also consider that many people around the world might be waiting for what you have to share.
This desire for intellectual exploration with others has been a big theme on my journey. But not until I added hope to my critical thinking and embraced a more expansive view of the world did I attract the kind of people I wanted to welcome into my conversation.
One of the goals of the pathless path is to make commitments: to a type of work, ways of living, creative projects, or a “conversation” with the world. A challenge here, however, is that the possibilities are so vast. Which raises a question: how do you begin to figure out what you want to do when there are not many limits?
Embracing the pathless path enabled me to see the possibilities for my life. This was exciting but also overwhelming. I often have the sense that I’d need multiple lifetimes to truly test and explore my options. Instead of embarking on an endless search, I’ve taken a different approach: working backward. Instead of thinking about what I want to do and how I want to live, I start instead with what I don’t want to be doing and what failure looks like. By looking at what might go wrong with our lives, we can avoid obvious traps, creating more space for things to go right. One useful mental model for thinking about this is the principle of inversion, popularized by German mathematician Carl Jacobi. He told his students to “invert, always invert,” encouraging them to approach difficult problems by inverting the equation to gain a new perspective. We can also apply this principle to our lives. For example, instead of asking what makes up an amazing life, we first define the worst‑case scenario and then work backward. What does a miserable life entail? What actions would make achieving such a life more likely? Then figure out how you can avoid these things from becoming true.
I encourage everyone to write a description of the person you don’t want to be, then brainstorm actions that might create that outcome. This exercise may be uncomfortable because undoubtedly you will see traces of the person you imagine in your present life. These traces are clues about what to change in your life right now.
Early on in my journey, I realized that my entire goal was to stay on the pathless path indefinitely. This is what author James Carse calls the “infinite game”: “A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.” By working backward, I realized that the biggest risks for me are spending my time doing things that undermine my ability to stay optimistic and energized, and obviously, running out of money. This is why I’ve spent so much time focusing on creating the conditions for success and lowering my risk of failure, rather than aiming at success itself.
Ultimately, figuring out what to do with freedom once we have it is one of the biggest challenges of the pathless path. Writer Simon Sarris argues that we can only do this by increasing our capacity for agency, or our ability to take deliberate action in the world. He argues, “the secret of the world is that it is a very malleable place, we must be sure that people learn this, and never forget the order: Learning is naturally the consequence of doing.” In other words, only by taking action do we learn and only by learning do we discover what we want. Without this, we will struggle to take advantage of the freedom that the pathless path offers. We are ultimately the ones that determine our fate, and without expressing agency, we struggle to be free.
When we think about the future, we tend to underestimate how much things will change, especially for ourselves. Researchers call this the “end of history illusion.” Across all age groups, people indicate that they have experienced profound change in the past but when they forecast their future, they don’t see the trend continuing. People believe that “the pace of personal change has slowed to a crawl and that they have recently become the people they will remain.” What can we do with this knowledge? For me, it’s made me more enthusiastic about embracing the pathless path because if I’m going to change more than I can expect, I might as well attempt to shape those changes. This is an alternative to how many people deal with change: by denying, delaying, or rejecting it. As we age we do become more mentally rigid and minor challenges to our routines can be landmines threatening to blow up our weeks, and suggestions that we live in new ways are treated as acts of war.
People aim for “financial independence” only to realize when they achieve it that they’re only independent in the narrow sense of being able to pay for everything. Realizing the flaws in this kind of economic thinking and inspired by writers like Eisenstein and Berry, I decided to experiment with the gift economy in my work. Based on Eisenstein’s book, I embraced three guiding principles:
Find ways to give without expectation of anything in return.
Be willing to receive gifts in any form and on any timeline.
Be open to being wrong about all of this and adjust my approach as necessary.
Everyone on the pathless path eventually needs to develop a strategy for approaching their journey. On the pathless path, once you open yourself up to possibilities and start experimenting with different ways of working and living, the biggest problem is the paradox of choice. There are too many interesting things worth doing and too many places to visit. To prioritize, developing a set of principles to help you make decisions is essential.
One of my most important is the mantra “coming alive over getting ahead.” I embraced this fundamental shift when I left my previous path, and the mantra reminds me that I don’t want to create another job for myself. When I see an opportunity to make money, scale something, charge more money, or move faster, this phrase reminds me to explore all possibilities first, including doing nothing/
This is one thing I think people get wrong about keeping options open. On the default path, optionality can be a trap. This is because you are trapped within your own career narrative. On the pathless path, however, optionality can pay consistent dividends because you are not holding out for another job but leaving space for a little more life.
In sum, the goal of being on this path is: Being able to get to a state of being where I can spend almost all my time helping, supporting, and inspiring others to do great things with their lives.
If the culture doesn’t work, don’t buy it. Create your own. This is what the pathless path is all about. It’s having the courage to walk away from an identity that seems to make sense in the context of the default path in order to aspire towards things you don’t understand. It’s to experiment in new ways, to remix your own path, to develop your own personal definition of freedom, and to dare to have faith that it will be okay, no matter how much skepticism, insecurity, or fear you face.
This book is my proposal for a new way forward. Which means things are in your hands now. To help you on your journey, I’ve put together a list of ten things. This is both a summary of many of the lessons from this book as well as a challenge for you as you embrace the spirit of the pathless path.
First, question the default. For many years, I stuck with a story about how I thought my life should go. I assumed there was only one option for structuring my life, around full-time work. I tried to be a “good egg” but ultimately, found myself unhappy with the direction my life was headed. I stumbled into a pathless path and slowly realized that a rigid version of the default path that existed in my mind was only one option of many.
Second, reflect. When I started reflecting on my true self, I was able to start building a life around the things I valued. Most of us run on autopilot through life but we can break out of this mode by considering even the simplest re"ection exercises. For me creating a daily reminder of four priorities that mattered to me and revisiting the leadership principles I aspired to in grad school helped me see that the gap between what I claimed to care about and how I was living was larger than I wanted. Through reflection, I was able to see that there was a larger “conversation” I was meant to have with the world.
Third, figure out what you have to offer. In our desire to be successful, we forget to notice how we are having an impact on others. One of the easiest ways to begin this exploration is to send a message to a few close friends, asking them, “when have you seen me at my best self?” Their responses may surprise you and, perhaps, delight you. We all have stories about who we think we are and why we must be that way but often, others have a better perspective on what makes us stand out.
Fourth, pause and disconnect. To improve your relationship with work, I believe it is necessary to disconnect. Unfortunately, a typical one or two-week vacation isn’t going to cut it. I believe that the minimum effective dose is at least a month away from work. While this may seem impossible or terrifying, this intervention has a near-universal approval rating and can have a profound effect on your con#dence about the future. If a month is scary, I suggest blocking off a random Tuesday afternoon, or another day in the workweek. Don’t tell anyone what you are doing and go wander. Go for a long walk, a bike ride, or sit by a river. Pay attention to the feelings that come up and see what they are telling you.
Fifth, go make a friend. Venture out of your existing bubble and reach out to someone who has taken an interesting path. Ask them how they got started, what motivates them, and how they think about navigating their life. Most people are much more enthusiastic about sharing what they’ve learned in their lives than we expect. To embrace the pathless path, you need friends and all you need at the start is one person. Over time, designing your work in a way that will help you naturally “find the others,” can be one of the most rewarding things of being on the pathless path and one of the most valuable things you can do in life.
Sixth, go make something. Remember, you are creative! Almost everyone has a desire to create something and to put their energy into the world in a positive way. It’s just that the legacy of the default path has convinced people that they need permission. But you know this is not true anymore. Find a way to create. Host a dinner party, organize a volunteer event, write a blog post, start journaling in the morning, paint a picture, or host a cooking class for your friends. It doesn’t matter what you do, but the sooner you figure out a way to create and share with the world, the faster you’ll be able to move closer to finding the activities you want to continue doing throughout your life.
Seventh, give generously. Generosity is not only an amount of money, it is a skill we need to practice. It is a way of orienting towards the world that will help you start to understand your own definition of “enough,” grapple with your hidden money scripts, and enable you to decouple your belief that security and money are perfectly linked. You don’t need to embrace the gift economy completely. Instead, you just need to pay attention and start making offers to share or give when the opportunity emerges. Ultimately giving is a superpower on the pathless path and will enable you to transcend feelings of separateness and connect more deeply to the people around you.
Eighth, experiment. The default path does not leave much space for experimenting with different ways of structuring your life. On the pathless path, you can prototype a change, work in different ways, take extended breaks, live in different countries, test your money beliefs, embrace unique fixed-point goals, and create things you never thought were possible. Remember, the goal is not to get rich but always to figure out what to do next.
Ninth, commit. Many people falsely think that escaping work is something worth aiming towards. I thought this at first but realized I had only thought about work as the things you do within a job. What I really wanted was the opportunity to feel useful and to do things that challenged me to grow. This is why I believe that the “real work of your life” is searching for the things you want to commit to and that make your life meaningful. Once you find them, you can dedicate your time to creating the environment to make those things happen.
Finally, be patient. In a famous letter to his friend Hume, Hunter S. Thompson argued that searching for the right path in life was important, even if it required many attempts. He told Hume that if he tried eight different paths and failed, that he must keep searching: “you must find a ninth path.” Embracing the pathless path can be a slow and frustrating journey, one that happens at a different speed for everyone. It took me years to build up the courage to quit my job and then several more years to find a mix of work, people, and a way of orienting in the world that felt like it was a path I was meant to be on. Don’t rush things. Remember: nothing good gets away, as long as you create the space to let it emerge.
The only thing left to do? Go and see what might happen if you dare to seek out, as the Poet Mary Oliver has called your “one wild and precious life”.