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Kindle Notes & Highlights
by
Paul Millerd
Started reading
October 25, 2023
We like to think that once we “make it” we can finally be ourselves, but based on who the companies selected, it was clear that the longer people stay at a company, the higher odds that they would become what the company wanted. I realized I didn’t want that to happen to me.
I had been on a path that wasn’t mine and to find a new way forward, I would need to step into the unknown.
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.
And I was able to keep moving when I realized that the hardest questions often don’t have answers.
Many people fall into this trap. 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.
I was too afraid to have a deeper conversation with myself. The kind that might pull me towards a different kind of life.
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.
he was attracted to the law profession because “the steps are laid out for you.” 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
The paths that Ranjit and I were drawn to also offered something else: prestige. Though hard to define, prestige can be thought of as the attention you get when you do things that others see as impressive. Paul Graham, the founder of a startup incubator and mentor to thousands of young people, sees this attention as a trap. In his view, prestige is “a powerful magnet that warps even your beliefs about what you enjoy.”12
I wasn’t picky about the type of work I’d be doing, I just wanted it to be seen as impressive.
Out of all the jobs I could get from my school, this was one of the best and the magnet of prestige convinced me that was what I wanted.
This is the trap of prestigious career paths. Instead of thinking about what you want to do with your life, you default to the options most admired by your peers.
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.” He believed “any other kind of life, if you lead it, will be the result of conscious and continuous effort.”
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.
He didn’t have a childhood filled with love and support. He chose to deal with it by trying to do better for his children and grandchildren and he succeeded. Like many of my cousins, we feel like we won the lottery growing up with a family like ours, where thanks to my grandfather we had access to a magical world filled with love, laughter, and possibility.
Those few days were filled with tears and overwhelming emotion, but also with beauty and a profound sense of meaning. The proof of his life’s work was in front of us. He had succeeded in creating a world better than the one he had grown up in. It was clear to me in those moments that family, love, and relationships were the most important things in the world.
That experience sent me down the “way of loss,” opening me up to the questions I had ignored by orienting my life around my work. 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? Difficult questions but ones that I was finally ready to contemplate.
Professors Richard Tedeschi and Lawrence Calhoun 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
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.”19
The educated, hardworking masses are still doing what they’re told, but they’re no longer getting what they deserve. – Seth Godin
No one wanted to grapple with this fundamental question: “Why the hell are so many grown adults spending their time on obviously pointless tasks?”
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
I had discomfort that could only be described the way Khe put it, as a pebble in my shoe. It wasn’t enough of a feeling to make me do anything dramatic, but it threw me off just enough that I was forced to pay attention to my life in a different way.
Are they happy? What kind of pain or challenges are they dealing with? Is this how they want to be spending their time? Once you ask these questions there is no going back. Not because of the contradictions in other people’s lives, but because it makes it difficult to live in contradiction in your own life.
Austin Kleon, a prolific creator and writer, says that “creative work runs on uncertainty; it runs on not knowing what you’re doing.”46
He came to the conclusion that “only intrinsic motivation lasts” and decided to leave a comfortable six‑figure salary behind and create a life designed around flexible work, his interests, and his family.47
the first step toward letting go of my deep attachment to the default path.
I did what I always did when I felt frustrated. I started looking for another job. I still thought the perfect job was just around the corner.
what if I paired making less with working less? I started to imagine a new path. Why not attempt to do the work I wanted to do as a freelancer while also having more flexibility and control over my life?
asks his clients this question, “How are you complicit in creating the conditions you say you don’t want?”
Professor Cary Cherniss’ definition of burnout as “the bureaucratic infringement on a professional’s autonomy” and thought that the right way to think about burnout was to focus on the disconnect between an individual and the culture of the company in which they worked.53
People dedicate themselves to being “good workers,” and being successful means keeping clients, customers, and managers happy while fitting into a company’s cultural norms. 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.
for some people, burnout involves the “dynamics of mourning” due to dealing with the “loss of something within yourself, something you treasured and valued, your ideals.”55 Freudenberger argued that recovering from burnout involves a grieving process to let go of those ideals.
“If work dominated your every moment, would life be worth living?” the philosopher Andrew Taggart offered a powerful question that spoke to the underlying tension I lived with for most of my adult life.
Yet when I became self‑employed, I was surprised at how strongly I had internalized a worker identity. As I struggled to find my first project, I felt guilty when I wasn’t working during typical work hours Monday through Friday. When I started working remotely on my first project, I had 100% control over when and how I did the work, but quickly fell into a routine of going to a coworking office five days a week. Many self‑employed people are surprised to find that once they no longer have to work for anyone else, they still have a manager in their head.
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: “If work dominated your every moment, would life be worth living?
My answer was becoming a clear “no,” but I didn’t know what this meant for my life. 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?
According to Taggart, living in a world dominated by total work undermines the “playful contemplation concerned with our asking, pondering and answering the most basic questions of existence.”58
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
This kind of approach, focused not on being brave, but instead on eliminating risk, is common for people who take unconventional paths.
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
We “ought to” keep working. This impulse is helpful most of the time, but compounded over one’s life it stops us from moving towards what Gilovich and Davidai call our “ideal self.”
“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
Making life changes requires overcoming the discomfort of not knowing what will happen.
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.
good grades, which were proof to other people that I was succeeding at a certain kind of game.
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.
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?”
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.
