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

by Paul Millerd

The conversational nature of reality is most apparent when you are willing to exist at “the frontier” of your current reality. As Whyte reflects, “It’s astonishing how much time human beings spend away from that frontier.” The default path keeps people from this frontier but the pathless path pushes you towards it. To Whyte, the cost of not moving towards the frontier is profound, as we often risk missing out on a “deeper, broader, and wider possible future that’s waiting.”

ambiguous questions ignited by losing my grandfather and losing my identity during my health crisis. This morphed into a more complex conversation over time, one that involved realizations from my life as well as from other people I was meeting through my writing. These connections were vital to staying at the frontier and exploring. In my favorite essay, “Solitude and Leadership,” William Deresiewicz highlights the importance of searching for wisdom in real conversations with close friends:

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.

the common trait they shared was seriously attempting to bring forth what was inside of them.

with him that the search for work worth doing is the real work and one of the most important pursuits in life.

More important is the realization that finding something worth doing indefinitely is more powerful and exciting than any type of security, comfort, stability, or respect a job might offer. Fighting for the opportunity to do this work is what matters, whether or not you make money from it in the short term.

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 co...

However, sometimes this impulse gets hacked by our shame and we follow paths that aren’t ours because we feel like the world’s love depends on us doing a certain thing. We are afraid that if we step away or make a change, we might be cast out of our family or community.

“humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.”

That is certainly important, but a more interesting path is possible if you start with what brought you alive in the past.

Many people struggle to start making a living from their creative endeavors because they are still operating within the logic of the default path.

And this group is diverse. As I’ve explored a broader range of topics such as self‑employment, freelancing, our relationship with work, and building an online business, I’ve met people from 13 to 75 years old, from the United States to New Zealand to Pakistan to China. As increasing numbers of people all around the world are tapping into the opportunities created by the internet, they are also looking for people like them. There has never been a better and easier time to find and connect with people in a positive

way.

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.”

we can avoid obvious traps, creating more space for things to go right.

Antifragility is a well‑documented natural phenomenon in which things gain strength through disorder.

Many believed that the end of World War I had concluded the struggle for freedom and the only problem left was what to do with it.

In his book The Art of Loving, he argued that the root of a positive version of freedom is a deep sense of connectedness with the world.

In addition to doing something challenging, “finding the others,” or discovering a different kind of work you enjoy, you might also find a mode of being that opens you up to a deeper relationship with the world and yourself.

without expressing agency, we struggle to be free.

People believe that “the pace of personal change has slowed to a crawl and that they have recently become the people they will remain.”161 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.

Professor and author Yuval Harari argued that “in order to keep up with the world of 2050, you will need not merely to invent new ideas and products, but above all to reinvent yourself again and again.”162 Nothing has helped me improve this skill more than living in other countries.

if coping with these challenges increased my confidence, is comfort overrated?

As more people invent new paths and enter new environments, communities, and online worlds, many will be forced out of their comfort zone. The sooner this happens the better because the era of living your entire life in a small, local, and familiar community is over. Whether we want to or not, we’ll have to keep reinventing ourselves.

I’ve done this over the past few years by looking at generosity as not merely a trait, but a skill that needs to be practiced. Practicing this skill has opened me up to a hidden side of life, filled not only with abundance, but also meaningful connection. I realized that this skill is worth practicing when I read a book called Sacred Economics by Charles Eisenstein. In it, he introduces the idea of a gift economy which he argues has been with humans for ages. He compares it to our default economic mindset:

Whereas money today embodies the principle, “More for me is less for you,” in a gift economy, more for you is also more for

me because those who have, give to those who need it. Gifts cement the mystical realization of participation in something greater than oneself which, yet, is not separate from oneself. The axioms of rational self-interest change beca...

If we had to form deep, meaningful relationships with everyone we interacted with within the economy, it would grind to a halt. However, the opposite is also true. When we look to the market to solve all our needs, it leaves us feeling empty. Professor

I sent her $100 via a payment app and walked away. When the thought first popped into my head, I noticed inner voices that told me it was a bad idea: “What if she wastes the money?” “Won’t this make her too lazy to take a job that might help her?” “She doesn’t deserve it.” Until that moment, I had always listened to those voices and leaned away from discomfort. However, this is the whole point of embracing the gift mindset and practicing generosity. It exposes our default scripts about how we think the world should work and opens us up to new possibilities.

I’m not in the business of being a business. I’m embracing the work of building a life and all of the connections that will make that meaningful.

When you find the work you want to keep doing, what makes it meaningful is that you are drawn to do it for its own sake. Seth Godin says that each of us carries an artist inside for whom it is imperative that we find the work we want to keep doing.

I agree with what Eisenstein noted in his study of gift economies “it’s the generous person who is the wealthiest.”170 The world may not fully agree, but at least

in my little corner of the

world, I can pretend it’s true and have a l...

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.

Coming alive over getting ahead.

resilient, and find a positive way to engage with my work and the world.

Why am I doing all this? Why does it matter so much?

I have bold aspirations. They may not be legible, measurable, or understandable to you, but they give my life a direction and a purpose. 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.

Create your own culture.

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.

“the world has become larger than your knowledge of it.”

After reading this book, you should no longer be able to look at your current path and think, “this is definitely the only way.” Instead, I hope you are able to shift to a place where you know that you have more freedom than you think, and your path can become something you choose again every day.

The answer, I realized, was a bit of both. You must be a little crazy to go against the grain of what most people think. Yet we should remind ourselves that these “experiments in living” as John Stuart Mill called them, are vital to pushing culture forward.

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 reflection 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 ...