The Pathless Path: Imagining a New Story For Work and Life (The Pathless Path Collection Book 1)

by Paul Millerd

Author Sebastian Junger, in his book about soldiers who had returned from war, found a similar thing. Despite dealing with post‑traumatic stress disorder, many of the soldiers wanted to return to dangerous warzones. Why? Because at war, they felt part of something, deeply connected to the men and women they were serving with. Junger reflected, “humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.”140 Junger argues that “modern society has perfected the art of making people not feel necessary.”

My friend Jonny Miller argues that “human existence is an infinitely unfolding process of remembering, forgetting, and remembering again.”141

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. Finding the right people, those who might offer support and encouragement along the way can have an outsized effect on your confidence and courage to keep going.

When I quit the New York Times to be a full-time mother, the voices of the world said that I was nuts. When I quit it again to be a full-time novelist, they said I was nuts again. But I am not nuts. I am happy. I am successful on my own terms. Because if your success is not on your own terms, if it looks good to the world but does not feel good in your heart, it is not success at all. – Anna Quindlen

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.151 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.

The default path has given us the freedom to earn money and spend it as we please, work in different fields, and have some control over our lives, but keeps many trapped in a pseudo‑freedom where one is free from absolute oppression but not free enough to act with a high degree of agency. The pathless path is the deliberate pursuit of a positive version of freedom. Revisiting Fromm’s definition, “the full realization of the individual’s potential, together with his ability to live actively and spontaneously,” we see that developing our own sense of agency is vital.159 Thus, figuring out what to do with your time is a real concern.

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.

To create your own culture on the pathless path you must identify the assumptions you make in your approach to life. Here are some of my assumptions, many of which have been sprinkled throughout this book: Many people are capable of more than they believe. Creativity is a real path to optimism, meaning, and connection. We don’t need permission to engage with the world and people around us. We are all creative, and it takes some people longer to figure that out. Leisure, or active contemplation, is one of the most important things in life, There are many ways to make money, and when an obvious path emerges, there is often a more interesting path not showing itself. Finding the work that matters to us is the real work of our lives.

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 confidence 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 othe...

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...

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.