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

by Paul Millerd

After spending the first 32 years of my life always having a plan, this kind of blind trust in the universe was new, scary, and exciting.

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.

it is better for reputation to fail conventionally than to succeed unconventionally.”

For my mother, it was being an active parent. Right from the start, she had an intuitive sense of my needs. She gave me space to make my own decisions and I learned how to take ownership of my life. She helped remove any obstacles in my way and helped me grow into a confident adult. At every step of my journey, the courage to take the next step was a direct result of her abundant love and compassion.

I know how much they sacrificed so that I would have better career opportunities. However, what they really gave me was so much more than the ability to succeed in school and work. It was space to dream, take risks, and be able to explore more possibilities for my life.

I am inspired by what the writer Leo Rosten once argued was the purpose of life: “to be useful, to be honorable, to be compassionate, to have it make some difference that you have lived and lived well.”

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

A career in the law signaled to others that he “was a serious and intelligent person.” But the longer he spent on the path, he realized that the real promise had been that “life’s existential fears are traded for certainty.”11

In describing the power of the inner ring, C.S. Lewis warns that, ”unless you take measures to prevent it, this desire is going to be one of the chief motives of your life, from the first day on which you enter your profession until the day when you are too old to care.”

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.

It was clear to me in those moments that family, love, and relationships were the most important things in the world.

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?

I had loosened my attachment to “Paul as a successful person,” but was still firmly located in that successful world.

When I come up for air, I realize how great things are, how lucky I am and that things aren’t so bad. I appreciate the friends and family that stick by me when things get ugly.

This is the hardest thing about being sick. It isn’t like a breakup when people tell you it will get better and you know they’re right. When you’re sick, you have to believe you will get better even though your body is telling you you’re crazy to think that.

It might surprise you that in Greece, during the time of Aristotle more than 2,000 years ago, work was simply considered a necessary evil. 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 else.”

In Anne Helen Peterson’s widely read essay “How Millennials Became the Burnout Generation,” she voiced her confusion with work as she wrote that she had “…internalized the idea that I should be working all the time. Why have I internalized that idea? Because everything and everyone in my life has reinforced it – explicitly and implicitly – since I was young.”

No one wanted to grapple with this fundamental question: “Why the hell are so many grown adults spending their time on obviously pointless tasks?”

I had studied advanced math and physics thinking I would apply those skills, but instead I spent my summers doing simple math on Excel spreadsheets. The notion of spending the rest of my life doing mindless busywork horrified me and motivated me to keep searching for better options.

My colleagues always laughed when I left the office at 5:30. “Paul can get away with it, he’s just different,” they would say. I thought I was simply more efficient and worried a little less. The reality was that I never bought into the wage‑based mentality and could never fully commit to placing work at the center of my life.

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

Austin Kleon, a prolific creator and writer, says that “creative work runs on uncertainty; it runs on not knowing what you’re doing.”

The only way through this kind of uncertainty is to embrace what author and educator George Leonard called “the spirit of the fool.” He argued that when you start learning anything new it will make you “feel clumsy, that you’ll take literal or figurative pratfalls. There’s no way around it.”48

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

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

Yet Taggart’s question remained a daily companion: “If work dominated your every moment, would life be worth living?”

In Winn’s version, finding your Ikigai means aligning what you love, what you are good at, what the world needs, and what can be paid for.

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.

Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.”

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.

However, some fear‑related problems cannot be solved. The authors of Designing Your Life offer a helpful reframe, calling these issues “gravity problems” which are part of life “…but, like gravity, it’s not a problem that can be solved.”

The final two questions of Ferriss’ exercise are the most powerful: What could be some benefits of an attempt or partial success? What is the cost of inaction in three months, 12 months, and in a few years?

Bronnie Ware has taken care of many elderly people in the final stages of their lives. In a blog post titled, “Five Regrets of The Dying,” one of the most viewed online posts, she shared her reflections. The most common regret? Not staying “true to themselves” in their lives and focusing too much on what others expected of them.

Will They Still Love You? I have talked with hundreds of people considering a change in their relationship to work or pursuing an alternative path, and one question consistently gets to the heart of their fears: “will the people in your life love you less if you do this?”

Are my friends as supportive as they seem, or do they think I’ve gone off the deep end?”

I’ve found the question, “will the people in your life love you less?” powerful because it addresses the scariest and deepest issues. I didn’t want to disappoint my parents. I desperately wanted to convince them that I was doing the right thing. However, had I understood that I feared losing their love, I would have realized that the wiser response would have been to open up my heart and be vulnerable.

Rebecca Solnit supplies the words I didn’t have at the time: 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 Chinese philosopher Lao Tzu wrote about this more than 2,500 years ago in the Tao Te Ching: “Less and less do you need to force things until finally you arrive at non‑action. When nothing is done, nothing is left undone. True mastery can be gained by letting things go their own way. It can’t be gained by interfering.”78 More recently, John Steinbeck channeled this sentiment in a letter to his son, telling him, “If it is right, it happens—The main thing is not to hurry. Nothing good gets away.”79

I discovered someone else who was asking the deeper questions and was willing to embrace uncertainty over doing what was expected. In other words, I had found someone fully embracing their own pathless path.

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.”

So I might add to Steinbeck’s advice: nothing good gets away, as long as you create the space to let it emerge.

After more than three decades of constantly planning for the future, I was able to start living in the present.

The incommunicable trees begin to persuade us to live with them, and quit our life of solemn trifles. – Ralph Waldo Emerson

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?”

The more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we’re too poor to buy our freedom. – Rolf Potts

the number of people who report being satisfied with retirement in an ongoing survey in the United States has been steadily falling for twenty years.87 Why might this be? Part of it is that when people stop working, they struggle to replace the meaning and joy they got from their work.

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.

Many people say things to me like “I could never live like you do!” All I can think, however, is “have you tested that?”