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

by Paul Millerd

The prime aim of life according to philosophers was “Eudaimonia,” which translates literally as “happiness,” but is better expressed as “flourishing.” In Aristotle’s words, “the more contemplation, the more happiness there is in a life.” Contemplating one’s place in the universe was seen as one of the most worthwhile things to do and at minimum, more important than the “money-making life,” which Aristotle described as “something quite contrary to nature…for it is merely useful as a means to something

Typically, I would be telling myself a story about how it was the perfect next step in my career.

In those first six months, I experienced a remarkable sense of freedom and ownership over my life.

As I embraced the freedom of self‑employment, I was opening up to this kind of leisure but was also still dealing with the lasting power of a world of total work that I had fully embraced, one where my perceived value was derived from my ability to keep working. Yet Taggart’s question remained a daily companion:

what it might feel like to live and work in a different way.

The more experiments I’ve done, the more comfortable I have become, and this gives me more freedom to try new things without being afraid.

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.

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.

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. The equation becomes: Uncertain Discomfort + Wonder > Certain Discomfort In thoughts about the future, worry is traded for wonder. People stop thinking about worst‑case scenarios and begin to imagine the benefits of following an uncertain path. They get curious about who they might become if they embrace discomfort and are filled with a sense of urgency that says, “if I don’t do this now, I might regret it.” Michael Ashcroft had worked as a consultant in the energy sector for almost ten years when he decided to quit and become self‑employed. An experience with burnout motivated him to prototype different kinds of work that might enable him to leave his job like teaching online

Facing uncertainty, we make long mental lists of things that might go wrong and use these as the reasons why we must stay on our current path. Learning to have a healthy distrust of this impulse and knowing that even if things go wrong, we might discover things worth finding can help us open ourselves up to the potential for wonderful things to happen. Only when you reach this state are you at the same point as Rubin was, with no questions left about taking the next step. And don’t worry, even if you do screw up a little, your “ought to” self is standing by, ready to help make things right. Seeing the World in a New Way Opening

putting in motion a plan to end my lease, sell most of my stuff, and return to Asia. In fact, they didn’t even find out from me, they heard it from my cousin. I was too scared of having the conversation.

“What will people think of me? I don’t even know what to think of me. Am I being

“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.

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.

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.”82 Similar frustrations with work inspired Jacqueline Jensen, a successful tech founder, to create a “structured sabbatical” to untangle her identity from her work. She asked herself, “What if I took work … working for a paycheck, what if I took that out of the center of my life, what would my life look like?” It was difficult, she says, “to untangle myself from all the things I get from work – the validation, the excitement.” 83 However, a month into her break she felt lighter and had a clearer view of what she wanted from work and life. 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 Third, people often desire to continue their “non‑work” journey. Lenny Rachitsky, who took a sabbatical after a long career in product management, thought he would return to work, “…but by the end of the break, it was crystal clear to me that I was ready to move on to a new adventure.” Several weeks into his sabbatical, he stopped checking his email: “My heart was no longer in the work. I didn’t yet know what I wanted to do next, but I knew it was time to shake things up.”85 Fourth, people write. When Alex Pang took a sabbatical after working in academia and the tech industry, he started to look at life differently, thinking, “maybe we had this idea about the relationship between working hours and productivity backward.”86 Based on that question alone, he spent the next several years writing and publishing several books about how rest and shorter workweeks might improve our lives.

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.

In his book, On Liberty, published in 1859, John Stuart Mill was giving similar advice, arguing that societies need people to embrace their individuality and perform “experiments in living.” He argued that such experiments are vital to the pursuit of knowledge and that cultures only learn and evolve when original approaches to living are discovered.

Mill argued that conventional ways of living tend to “degenerate into the mechanical’’ and that if societal norms are too strong or rigid, original thinkers who would otherwise experiment will be stifled.

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.

I’ve found a clear answer: having ownership of my time enriches my life.

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.

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.

Many people I talk to are convinced that the formula for living on their own terms is saving up enough money. I wish they knew what I know: the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is. Money might help pay for therapy, time off, and healing retreats, but it won’t help you come to a place where you really trust and know that everything will be okay.

Having faith does not mean being worry‑free. I still worry about money, success, belonging, and whether I can keep this journey going. However, I’m able to recognize that the right response is not to restructure my life to make these worries disappear. It’s to develop a capacity to sit with those anxieties, focus on what I can control, and to open myself up to the world. As the spiritual teacher Sharon Salzberg has written, “whatever takes us to our edge, to our outer limits, leads us to the heart of life’s mystery, and there we find faith.”

and the only way to develop room for faith in your life is to do exactly as Salzberg says, explore the limits and step into the possibilities for our life. The fact that the next steps are unknown to us is exactly the point.

It was incredibly painful for me to realize that if I truly cared about living in a different 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 offer, from ambition to aspiration, and from hoping that joy will result from a specific outcome to experiencing it as a byproduct of your journey.

I’m in an indie economy, where over the long‑term I’m competing on learning, developing skills, and my reputation. This is a lot harder but also a lot more rewarding. Despite this, it’s interesting to see how people map their own understanding of how they think the world works onto my current path.

The world is changing and the pathless path is just one way to exit the world of bad tests. As more and more people decide that these tests are silly, we can create new and better games.

This also exposed me to a new kind of prestige that I wasn’t allergic to – recognition

from other people who are passionate about ideas.

If the default path is the story of the industrial world, then the pathless path is the natural story for a digital‑native world in which nothing can stop us from finding others who share our desires, ideas, and questions.

little more suspicious of anyone who seems to think there is one true way of working.

As he reflected later, “it sounds so lame, but to me a big portion of success was other people thinking I was successful.”

Lowry had reached the heights of success in his field, but when that was taken away, he realized he did not have the skills needed to embark on a new path.

The only way forward is to eventually get to a point when you realize that, in fact, there are no good eggs or bad eggs at all. The pathless path is about releasing yourself from this way of seeing the world and realizing that the number of career paths worth following is infinite.

Find Your “Enough” Are you helping people? Are they happy? Are you happy? Are you profitable? Isn’t that enough? – Derek Sivers

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.

$7,500, which would fund my life for several months, but when I started working on the project, I realized I had talked myself into the project in order to calm my fears rather than as something I was excited to work on. I committed to not making the same mistake again.

Yet in my experience, no amount of money ever seems to satisfy. Becker argues that the only way to transcend these existential fears is to live a life that feels heroic. He argues that “if everyone honestly admitted his urge to

What he means by heroic is less about saving the world and closer to the pathless path: a journey of finding yourself, grappling with your insecurities, and daring to seek out a life that is uniquely yours. Becker argues that prescribed paths of the modern world can trap people into conforming to the expectations of others instead of taking steps to create their own unique path.

Do I still worry about money? Yes. But now I’m hyper‑aware of how my financial insecurities might distract me from efforts that will help me stay energized and motivated on this path. Instead of playing to not lose, I’m playing to win.

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 u...

real secret: the opportunities of the pathless path ...

One of the best ways to discover your conversation is to start asking questions driven by your curiosity. For me, some of my favorite questions include: What matters? Why do we work? What is the “good life”? What holds people back from change? How do we find work that brings us alive?