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by
Paul Millerd
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June 27 - August 20, 2022
I adopted this attitude and embraced a version of a career which philosopher Andrew Taggart, who writes about our modern relationship to work, describes as “a first-person work‑centric story of progress about an individual’s life course.”15
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.
As I started to feel better, a different kind of energy showed up in my life. 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.”
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.
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.”
Religious scholars point out that the Protestant “work ethic” is more than a blind obsession with work. It is paired with thrift, self-discipline, and humility. Yet as fewer people look to religion for wisdom on how to navigate life, they are only left with the watered‑down version of these views.
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.”
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
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 When he got raises or promotions the discomfort would subside but never disappear. Slowly, he became more curious about that feeling and realized that despite his external success, he had become a “passive participant” in his life. Eventually, this convinced him to embark on his own pathless path.
“How do you design a life that doesn’t put work first?”
Some people inherit values and practices as a house they inhabit; some of us have to burn down that house, find our own ground, build from scratch, even as a psychological metamorphosis. – Rebecca Solnit
“How are you complicit in creating the conditions you say you don’t want?”
The norms of the organization were pulling me too far away from the person I wanted to be and the energy I used to manage this disconnect undermined anything good I had to offer.
Many people dislike some parts of their jobs. But they stay in their jobs because their suffering is familiar. To change would be to trade the known for the unknown and change brings discomfort in hard to predict forms.
Before he left his job, he told me, “I have a suspicion that a whole bunch of energy will get unlocked. I’ll just start doing things, and creating things and talking to people, and going to places…that I cannot fundamentally imagine right now, and it will be that stuff that shapes my life going forward…I am curious what else will show up.”65 He was able to take the leap because he had tapped into the power of wonder, enabling him to be excited about an uncertain future.
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.
people on aspirational journeys, or what I call the pathless path, are “characteristically
needy people.” Because their worldviews are incomplete and evolving, they are dependent on the support of other people.
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.
“We must let go of the life we have planned, so as to accept the one that is waiting for us.”
“I used to think ‘this job isn’t so bad, I make enough money to make it worth it.’ Then you get a breath of freedom and realize, no, it may have been worth it at one point, but not anymore.”
the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is. Money might help pay for therapy, time off, and healing retreats, but it won’t help you come to a place where you really trust and know that everything will be okay.
Dr. Ben‑Shahar calls the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness.
How does one get lots of users? They had all kinds of ideas about that. They needed to do a big launch that would get them ’exposure.’ They needed influential people to talk about them. They even knew they needed to launch on a Tuesday, because that’s when one gets the most attention. No, I would explain, that is not how to get lots of users. The way you get lots of users is to make the product really great.
The internet does enable negative groups to form, but we pay far too much attention to these communities and not enough to the positive connections and life options made possible all over the world for people who are online.
This is why I’m fond of the advice angel investor Naval Ravikant offers, “play long‑term games with long‑term people.” Ever since making that first friend from
Enough is the antithesis of unchecked growth because growth encourages mindless consumption and enough requires constant questioning and awareness. Enough is when we reach the upper bound of what’s required. Enough revenue means our business is profitable and can support however many employees/freelancers we have, even if it’s just one person. Enough income means we can live our lives with a bit of financial ease, and put something away for later. Enough means our families are fed, have roofs over their heads and their futures are considered. Enough stuff means we have what we need to live our
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“if everyone honestly admitted his urge to be a hero it would be a devastating release of truth.”
In my favorite essay, “Solitude and Leadership,” William Deresiewicz highlights the importance of searching
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.132
John learned the same lesson I had in taking the client that had drained my energy. No money is worth it if it undermines your desire to stay on the journey.
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. This is one of the most important secrets of the pathless path. With this approach, it doesn’t make sense to chase any financial opportunity if you can’t be sure that you will like the work. What does make sense is experimenting with different kinds of work, and once you find something worth doing, working backward to build a life around being able to keep doing it.
The Great Work of Your Life
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.
Instead of looking to external cues to learn how to live, we need to have a coherent internal narrative about why we are living a certain way. This is the ethos of the pathless path and if you don’t know or understand your own story, you will struggle.
“The world just gave you control over the means of production. Not to master them is a sin.”
Tyler Cowen has argued that one of “the most valuable things you can do with your time and with your life” is to believe in people.
any time I consume something from an individual that inspires me, I have to send them a note to let them know.
backward. Instead of thinking about what I want to do and how I want to live, I start instead with what I don’t want to be doing and what failure looks like. By looking at what might go wrong with our lives, we can avoid obvious traps, creating more space for things to go right.
During my time on the default path, I often imagined a future version of myself that I knew I didn’t want to be: an overweight guy in his 50s who barely tolerates the people in his life, hates his job, spends his days in a windowless cubicle farm, and isn’t very happy. If you had known me then, you would have said I would never have ended up like that. However, by the time I left my job I was much closer to that person than when I started.
I submit that this is what the real, no‑bullshit value of your liberal arts education is supposed to be about: how to keep from going through your comfortable, prosperous, respectable adult life dead, unconscious, a slave to your head and to your natural default setting of being uniquely, completely, imperially alone day in and day out.
“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.”
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 because the self has expanded to include something of the other.
