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Kindle Notes & Highlights
by
Paul Millerd
Read between
January 26 - January 29, 2023
Whyte says that when we first encounter the idea of a pathless path, “we are not meant to understand what it means.”
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.
that most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them.
I had been following a formula for life that was supposed to guarantee happiness. It didn’t. Confusion kept me on a path that wasn’t mine for more than ten years.
This means that for many people, expectations of life are centered around a small number of positive events that occur while we are young. Much of the rest of our lives remains unscripted and when people face inevitable setbacks, they are left without instructions on how to think or feel. While very few young people expect
have one job or career, most still rely on the logic of the default path and assume they need to have everything figured out before the age of 25. This limits the ideas of what we see as possible and many, including me, internalize the “worldly wisdom” that John Maynard Keynes once pointed out, “that it is better for reputation to fail conventionally than to succeed unconventionally.”
We are convinced that the only way forward is the path we’ve been on or what we’ve seen people like us do. This is a silent conspiracy that constrains the possibilities of our lives.
For most of my life, I’ve had the gift of seeing the greatness in others. It hurts when I see people stuck or unable to pursue their dreams, and I want to do anything I can to help them.
“to be useful, to be honorable, to be compassionate, to have it make some difference that you have lived and lived well.”
Helping people live courageously so that they can thrive is one of the most important things in the world. I want to see people live the lives they are
capable of, not just the ones they think they are allowed to live.
philosopher Andrew Taggart believes that crisis moments lead to “existential openings” that force us to grapple with the deepest questions about life.16
have suggested that many people who face crises often experience “post-traumatic growth” and that this manifests as an “appreciation for life in general, more meaningful interpersonal relationships, an increased sense of personal strength, changed priorities, and a richer existential and spiritual life.”17
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.”
Plus, I was too busy getting sucked into a new idea. That you didn’t simply work to live, but that it should be one of the most important things in your life.
The notion of spending the rest of my life doing mindless busywork horrified me and motivated me to keep searching for better options. It’s also what drove me to try to break into strategy consulting where I wouldn’t have to spend so much time proving I was willing to do things I didn’t believe in.
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.
People want to hear about bold acts of courage, not years of feeling lost. On my way toward leaving my job, I never had a clear picture of my next step.
he walked away to find a new
path. However, it took him a long time to make that decision. He reflected, “It definitely wasn’t a sudden realization. It’s a little bit like having a pebble in your shoe, where you’re walking and something is off, and it’s mildly uncomfortable.”45
new eyes. Are they happy? What kind of pain or challenges are they dealing with? Is this how they want to be spending their time?
My final list included four items: health, relationships, fun & creativity, and career.
Without knowing it, I had embraced a question that would shape my decisions: “How do you design a life that doesn’t put work first?” The answer, my dear reader, is simple. You start underachieving at work.
My view of the world was shifting and it was both exciting and disorienting. Austin Kleon, a prolific creator and writer, says that “creative work runs on uncertainty; it runs on not knowing what you’re doing.”46 The creative work of finding a new life path is similar. I acknowledged as much in that email announcing
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 I liked feeling like a fool and the excitement that comes with learning something new.
would have been shocked. But I also would have thought that was exactly what I wanted. As I sat there, I didn’t know how to want it anymore. I had been hired to help build a consulting division. The success I achieved
Unfortunately, success for the company does not always align with what is best for the person, and over time, a disconnect can emerge. This is what happened to me.
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
“If work dominated your every moment, would life be worth living?”
Are you a worker? If you are not a worker, then who are you? Given who you are, what life is sufficient?
For the first time, I was able to deeply know the type of leisure that Pieper wrote about. This was also confusing. When people asked how my work was going, I offered a hand‑wavey response, trying to hide my guilt of pursuing such a radical experiment. Yet my excitement for life grew and my curiosity soared. I felt drawn to creative projects again as I had been in New York. One was a blog.
around meaningful work, far too many people limit their imagination of work worth doing to things that either come with a paycheck, require qualifications, or have a socially accepted story of impact.
For me, I was finding that the act of creation was the reward itself. The philosopher Erich Fromm has argued that “creative union,” or when “man unites himself with the world in the process of creation,” is a way to experience love.62 I would have thought this completely absurd if I had not felt the depths of my connection to the world in those months. After a few months of this, I was completely open
As I wandered Asia, my mind exploded with possibility. If it was possible to work from a laptop in Bali, what else had I not yet considered?
EconoMe for people like her who were reimagining the American Dream, and she continued to engage in many other projects beyond her job.
“I’ve come to a point where I’d rather fail as a writer than succeed as a lawyer, and I need to try and fail or try and succeed, but I need to do it.”68 Rubin attended Yale
path, I had to find inspiration from podcasts and social media where people like Seth Godin, Derek Sivers, and Tim Ferriss exposed me to a broader set of ideas of how to live and work.
One of the ideas that Seth Godin is known for is his suggestion that people on unconventional paths seek to “find the others.” These are the people who give us inspiration that doing things differently is possible and who might even join us on our journey.
When you meet others on a similar path, there is an instant bond and a deep sense of knowing about the challenges you are both going through. You can smile in a way that says, ”I know, I know,” skip the “what do you do?” question, and start a deeper conversation.
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. Writing about fears has helped me transform abstract worries into concrete issues. When I wrote that I was afraid of going broke after I quit my job, I realized that there were fifty different things I could do to make money.
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?
The most common regret? Not staying “true to themselves” in their lives and focusing too much on what others expected of them.
Unfortunately, the pathless path is an aspirational path and can never be fully explained, as Callard tells us, so attempts to convince people that you are moving in the right direction can be futile. People who value comfort and security often cannot understand why anyone would willingly pursue a path that increases discomfort and uncertainty.
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.
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.77
I was lost in both the story of my life and in this new place where I couldn’t read the signs or speak the language. Yet I also felt I was exactly where I was supposed to be, my days filled with lightness and ease. This feeling contrasted with the daily tension and low‑grade anxiety that I had experienced in New York and Boston over the previous ten years. In Taipei, that feeling evaporated and I started to experience a lighthearted playfulness that had remained dormant since I had wandered in the woods as a kid.
“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
