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

by Paul Millerd

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.

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.

The pathless path has been my way to release myself from the achievement narrative that I had been unconsciously following. I was able to shift away from a life built on getting ahead and towards one focused on coming alive. I was able to grapple with the hard questions of life, the ones we try so hard to ignore. And I was able to keep moving when I realized that the hardest questions often don’t have answers.

The pathless path has been my way to release myself from the achievement narrative that I had been unconsciously following. I was able to shift away from a life built on getting ahead and towards one focused on coming alive. I was able to grapple with the hard questions of life, the ones we try so hard to ignore. And I was able to keep moving when I realized that the hardest questions often don’t have answers.

One of the biggest things the pathless path did for me was to help me reimagine my relationship with work. When I left my job, I had a narrow view of work and wanted to escape. On the pathless path, my conception expanded, and I was able to see the truth: that most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them. It is only when we cling to the logic of the default path that we fail to see the possibilities for making that happen.

One of the biggest things the pathless path did for me was to help me reimagine my relationship with work. When I left my job, I had a narrow view of work and wanted to escape. On the pathless path, my conception expanded, and I was able to see the truth: that most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them. It is only when we cling to the logic of the default path that we fail to see the possibilities for making that happen.

The philosopher Andrew Taggart believes that crisis moments lead to “existential openings” that force us to grapple with the deepest questions about life.16 He argues there are two typical ways this happens. One is the “way of loss,” when things that matter are taken from us, such as loved ones, our health, or a job. The other path is the “way of wonderment,” when we are faced with moments of undeniable awe and inspiration.

That experience sent me down the “way of loss,” opening me up to the questions I had ignored by orienting my life around my work. What was I living for? What did I really want? How did I want to look back on my life when it was my time to go? Difficult questions but ones that I was finally ready to contemplate.

While I was sick, I had contemplated the question, “what would people think if I couldn’t work again?” and had been surprised by my answer. I would be okay. 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.

Despite thinking I wanted fun and joy at work for most of my career, when I reflect on the most meaningful moments of my career, they involve overcoming obstacles, or getting through setbacks to complete something I didn’t think I could.

McKinsey & Company found similar trends across Europe and estimated that more than 100 million people across the United States and Europe are now “nontraditional” employees. McKinsey compared these workers to “traditional” employees and found that they were as satisfied or more satisfied across fifteen different work characteristics, such as income, independence, hours, flexibility, creativity, and even recognition.44 Though this group is quite large, it doesn’t have a cohesive voice, and people are often surprised to find that most of these “alternative” workers are quite happy.

The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything. – David Foster Wallace

I had no master plan to quit my job. Even now, several years after doing so, when people ask about my journey, I’m more confused than you might expect. Choosing to leave full‑time work was not a single bold decision but a slow and steady awakening that the path I was on was not my path.

“How do you design a life that doesn’t put work first?” The answer, my dear reader, is simple. You start underachieving at work. You stop setting an alarm and you cancel morning meetings because the energy gained is worth fighting for. You start working remotely on Fridays without asking because the extra 24 hours with your grandmother is worth it. You start taking naps at the office because there’s a nap room and someone has to use it, right? I felt like a rebel, like I was doing something wrong. At the same time, I had the sense that taking ownership of my life in this way, especially to prioritize my health, was something worth doing. Instead of being consumed with thoughts about work and my next step, I had time to continue to experiment, and in the space that emerged, a creative energy entered which started to become a central force in my life.

When we talk about our jobs we often say, “I’m learning a lot!” In the first few years working in consulting, this was true. I grew in so many areas: writing, giving better presentations, communication skills, and research. A few years into the path, however, the things I was incentivized to learn became specific to the organization, such as navigating political conflicts and adopting behaviors, dress, and attitudes that signaled I might be a future company leader. I sucked at these things and my motivation tanked.

A passage from William Reilly’s book How To Avoid Work, published in 1949, captures my reality at the time: Your life is too short and too valuable to fritter away in work. If you don’t get out now, you may end up like the frog that is placed in a pot of fresh water on the stove. As the temperature is gradually increased, the frog feels restless and uncomfortable, but not uncomfortable enough to jump out. Without being aware that a chance is taking place, he is gradually lulled into unconsciousness. Much the same thing happens when you take a person and put him in a job which he does not like. He gets irritable in his groove. His duties soon become a monotonous routine that slowly dulls his senses. As I walk into offices, through factories and stores, I often find myself looking into the expressionless faces of people going through mechanical motions. They are people whose minds are stunned and slowly dying.49

These questions inspired an idea: what if I paired making less with working less? I started to imagine a new path. Why not attempt to do the work I wanted to do as a freelancer while also having more flexibility and control over my life?

At that last job, I wasn’t a team player and I could have tried harder to say the right things, dress the right way, or spend more time pleasing my manager. But I couldn’t do it. The norms of the organization were pulling me too far away from the person I wanted to be and the energy I used to manage this disconnect undermined anything good I had to offer. A German report on burnout found that when burned out, people “may start being cynical about their working conditions and their colleagues…” and may “…distance themselves emotionally and start feeling numb about their work.”54 This is the tricky thing about burnout. If you are suffering from burnout, you are likely not thriving at work, and over time it’s easy to see yourself as the cause. Add to this the common assumption that you should never leave a job too soon and you get a world in which millions of people are experiencing the slow, marginal creep of burnout and have no way out.

Professor Freudenberger noted in his research that for some people, burnout involves the “dynamics of mourning” due to dealing with the “loss of something within yourself, something you treasured and valued, your ideals.”55 Freudenberger argued that recovering from burnout involves a grieving process to let go of those ideals. I had not factored this into my journey and did not expect how hard it would hit me in that first month. I settled into a slower pace as my trip through Europe shifted from a celebration to rest and recovery.

“If work dominated your every moment, would life be worth living?” the philosopher Andrew Taggart offered a powerful question that spoke to the underlying tension I lived with for most of my adult life. By my late 20s, I had oriented my entire life around work. I was always thinking about how I could get a better job or a higher salary. I had launched a side gig helping people navigate their careers and started writing about how the working world could be better. I could only afford my expensive New York City apartment because I was earning a high income, and my social life was spent with similarly high‑earning friends. At the time I could not imagine any other existence. Where I lived, what I did, how I thought about money, and the people I hung out with were all connected with my work identity.

Yet when I became self‑employed, I was surprised at how strongly I had internalized a worker identity. As I struggled to find my first project, I felt guilty when I wasn’t working during typical work hours Monday through Friday. When I started working remotely on my first project, I had 100% control over when and how I did the work, but quickly fell into a routine of going to a coworking office five days a week. 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.

Pieper argued that for most of history, leisure was one of the most important parts of life for people in many cultures. He noted that 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.”57

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.

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.

Many people dislike some parts of their jobs. But they stay in their jobs because their suffering is familiar. To change would be to trade the known for the unknown and change brings discomfort in hard to predict forms. So people avoid change and develop coping strategies. They learn to sidestep the manipulative manager, or like me, change jobs every couple of years, plan vacations, stay busy, and get drunk during the weekend. Play this game long enough without becoming too burned out and you might end up getting promoted.

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.

On my previous path, there was a hidden cost to my success. The consistent financial rewards helped me live a smooth existence, needing to rely less on others the more I succeeded. In some circles, this is celebrated as the ultimate aim of life, but for me it led to a certain emptiness that I didn’t fully understand until I found myself on a path that forced me to find the others.

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.74 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.

In seven days, I’ll be boarding a flight to Taipei to begin a chapter in my life of living and working nomadically. As I’ve simplified my life and embraced minimalism, I noticed that I have had more time and have been in less of a rush to “do things,” giving me the chance to take routes that don’t make sense, go for random walks through the city and make time to have conversations I wouldn’t otherwise have. I feel so lucky and as I make the shift to Taipei, it seems much less a “vacation” or “trip” and much more an extension of an increased appreciation for life and the people in it.

I now agree with Joseph Campbell, who through his study of the human experience through our ancestors’ stories, concluded that “We must let go of the life we have planned, so as to accept the one that is waiting for us.”80 So I might add to Steinbeck’s advice: nothing good gets away, as long as you create the space to let it emerge.

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. After my friend, Kevin Jurczyk, took a planned sabbatical, he shared with me, “I used to think ‘this job isn’t so bad, I make enough money to make it worth it.’ Then you get a breath of freedom and realize, no, it may have been worth it at one point, but not anymore.”

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 find 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.”84

surprised by how different life feels when it is not structured around work. We also became aware that our previous paths had kept the possibilities for our lives hidden, and in a short time, we started to recapture a youthful energy, one that enabled us all to take bold steps towards different kinds of lives.

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?”88 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.”89 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?

No underlying logic justified my spending and a lot of it could be classified under what writer Thomas J. Bevan calls a “misery tax.” This is the spending an unhappy worker allocates to things that “keep you going and keep you functioning in the job.”96 For me, it was a mixture of alcohol, expensive food, and vacations, and as the amount inched up during my career, I started to believe that my spending was the reason I was working.

With money coming in and a lower cost of living, my financial insecurity decreased, leading to a chain reaction in my understanding of work. If I wasn’t working for money, why was I working? When we work full‑time, employers are paying for our dedication and commitment to the job as a central part of our life. When I became self‑employed, I was disoriented because the people paying me for the projects didn’t care when and how much I worked. They just wanted their problems solved. It was up to me to figure out how to spend my time.

Working on my own, I had infinite degrees of freedom to shape what I worked on, who I worked with, and how much I worked. When people on the pathless path first discover this possibility, it can be jarring. Opting out of work and opting in to other aspects of your life can create questions about who you used to be. It feels weird at first, but over time, you start to change what you value. As I unlocked more time for creative projects, travel with my family, time with my grandmother, and time for learning, I was finally doing the things I claimed to care about. No amount of money can buy the peace of mind that comes with finding a path that you want to stay on. Once we know, as Vicky Robin argues in her book Your Money or Your Life, that “money is something we choose to trade our life energy for,” it is nearly impossible to give up your time for money without thinking deeply about the trade-offs.97

With freelancing, I was competing on the quality of my ideas and my ability to do good work for clients. A lot of former consultants who become freelancers are surprised at how much less time it takes to do the same work. This is not because it’s any easier. In fact, it’s a lot harder without the support of an entire firm’s resources. It’s just that there are no longer hundreds of different people you need to impress.

Coming to this understanding requires a lot of reflection and experimentation, but surprisingly, this is often much easier on the pathless path than the default path. Because I work for myself, I spend zero minutes a year blaming other people for my circumstances. It forces me to take complete ownership of my life and continue to experiment, reflect, and try again. In six months I can experiment with my life in many more ways than I did in the ten years I spent on the default path, allowing me to learn much more quickly.

Enough is the antithesis of unchecked growth because growth encourages mindless consumption and enough requires constant questioning and awareness. Enough is when we reach the upper bound of what’s required. Enough revenue means our business is profitable and can support however many employees/freelancers we have, even if it’s just one person. Enough income means we can live our lives with a bit of financial ease, and put something away for later. Enough means our families are fed, have roofs over their heads and their futures are considered. Enough stuff means we have what we need to live our lives without excess.125

Enough is knowing that no amount in my bank account will ever satisfy my deepest fears. It’s knowing that I have enough friends that would gladly open their door and share a meal if I was ever in need. It’s the feeling that I’ve been able to spend my time over an extended stretch of time working on projects that are meaningful to me, helping people with a spirit of generosity, and having enough space and time in my life to stay energized to keep doing this over the long‑term. Enough is seeing a clear opportunity that will increase my earnings in the short‑term, but knowing that saying “no” will open me up to things that might be even more valuable in ways that are hard to understand. Enough is knowing that the clothes, fancy meal, or latest gadget will not make me happier, but also that buying such things won’t mean I’m going to end up broke. Enough is having meaningful conversations with people that inspire me, people that I love, or people that support me.

On the pathless path, knowing you have enough is what gives you the freedom to say “no” to clear financial opportunities and say “yes” to something that might bring you alive and might even pay off much more over the long term.

If we don’t define “enough,” we default to more, which makes it impossible to understand when to say no.

What I’ve discovered in conversations is that no matter how much money people have, they will go to enormous lengths to avoid any discomfort related to their financial situation. This is what makes quitting full‑time employment seem terrifying and a steady paycheck so addictive.

Behind our money fears are existential fears, like the fear of death or the fear of not being loved, respected, and admired. These fears are likely not solvable but we can learn to coexist with them. This is also why financial worries can be infinite and people can chase more and more their entire lives. The flip side of this is that if we can learn to coexist with our financial insecurities, we can turn them into a secondary concern. This opens you up to the real secret: the opportunities of the pathless path are infinite too.

Introspection means talking to yourself, and one of the best ways of talking to yourself is by talking to another person. One other person you can trust, one other person to whom you can unfold your soul. One other person you feel safe enough with to allow you to acknowledge things—to acknowledge things to yourself—that you otherwise can’t. Doubts you aren’t supposed to have, questions you aren’t supposed to ask. Feelings or opinions that would get you laughed at by the group or reprimanded by the authorities.

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.

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 work I get paid for may shift over time, and it may or may not involve the things that I want to keep doing. But what I want to keep doing, such as mentoring young people, writing, teaching, sharing ideas, connecting people, and having meaningful conversations, is worth fighting for.