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

by Paul Millerd

the world continues to change and technology reshapes our lives, the stories we use to navigate life become outdated and come up short. People are starting to feel the disconnect between what we’ve been told about how the world works and what they experience. You work hard, but get laid off anyway. You have the perfect life on paper, but no time to enjoy it. You retire with millions in the bank, but no idea what to do with your time.

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.”2 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.3

The ease of having an ambition is that it can be explained to others; the very disease of ambition is that it can be so easily explained to others. – David Whyte

In Weber’s view, a “traditionalist” view of work is one where people work as much as they need to maintain their current lifestyle, and once that aim is achieved, they stop working.

Catholic and Protestant perspectives on work are deeply embedded in the modern default path view of work that spans the globe but has become detached from the time periods and traditions from which they emerged.

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

there are clear boundaries to behavior within a given field of endeavor, then there is also great freedom to adapt and imagine within those lines. These boundaries, however, should always be tested to see if they are actually still real. It takes conscious acts by individuals to test these edges. – David Whyte

“How do you design a life that doesn’t put work first?” The answer, my dear reader, is simple. You start underachieving at work.

Jerry Colonna, an investor turned executive coach, asks his clients this question, “How are you complicit in creating the conditions you say you don’t want?”

Pieper pointed out that people “mistake leisure for idleness, and work for creativity.”

Eventually, I reached out to Taggart directly and he proposed three more specific questions: Are you a worker? If you are not a worker, then who are you? Given who you are, what life is sufficient?

The one who wonders not only does not know, he is intimately sure that he does not know, and he understands himself as being in a position of not‑knowing. But this un‑knowing is not the kind that brings resignation. The one who wonders is one who sets out on a journey, and this journey goes along with the wonder: not only that he stops short for a moment, and is silent, but also that he persists in searching. – Joseph Pieper

This kind of approach, focused not on being brave, but instead on eliminating risk, is common for people who take unconventional paths.

Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.”69 This is in contrast to an ambitious journey where we already know what we value.

That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.

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.

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?

In my favorite essay, “Solitude and Leadership,” William Deresiewicz highlights the importance of searching for wisdom in real conversations with close friends: 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.

If we let ourselves, we shall always be waiting for some distraction or other to end before we can really get down to our work. The only people who achieve much are those who want knowledge so badly that they seek it while the conditions are still unfavorable. Favorable conditions never come. – C.S. Lewis

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.

If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you.

“critical thinking without hope is cynicism. But hope without critical thinking is naïveté.”

I read a book on writing by William Zinsser. He urged me to “believe in your own identity and your own opinions. Writing is an act of ego, and you might as well admit it. Use its energy to keep yourself going.”

The biggest challenge to creating your virtuous cycle and one of the most dangerous failure modes of the pathless path is cynicism. Many people who leave the default path do so because they’ve become cynical and are driven by a desire to escape. But escaping is only the first step of leaving a certain path behind. In order to create a sustainable journey and path, it requires finding ways of orienting to the world that leave space for hope.

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.

I’ve found no better advice than the following from Dolly Parton: “Find out who you are and do it on purpose.”160

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.”

Until the 1600s when clocks became ubiquitous, people rarely thought about time. English historian E.P. Thompson noted that instead, people thought in terms of activities. In Madagascar, a half-hour was a “rice cooking,” and a brief moment was “frying a locust.” When they had clocks, people increasingly thought about time as something related to money. Thompson noted that “time is now currency, it is not passed but spent.”

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.

“Dying,” Morrie suddenly said, “is only one thing to be sad over, Mitch. Living unhappily is something else. So many of the people who come to visit me are unhappy.” Why? “Well, for one thing, the culture we have does not make people feel good about themselves. We’re teaching the wrong things. And you have to be strong enough to say if the culture doesn’t work, don’t buy it. Create your own.”

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. Could I be wrong about these things? Definitely. But the pathless path is not about being right. It’s about finding ideas and principles worth committing to and seeing where you end up. Without doing this, you are accepting the logic of the default path.