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Kindle Notes & Highlights
by
Paul Millerd
Read between
January 29 - January 31, 2023
Making life changes requires overcoming the discomfort of not knowing what will happen.
In the months leading up to leaving my job and the year or two after quitting, I struggled to make sense of my journey. When others asked how I was doing, I felt compelled to give them proof that I had a plan and knew what I was doing.
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.
Aspirational pursuits go hand in hand with the pathless path because they can appear incomprehensible to others and even yourself, sometimes for years.
Learning to exist with this vagueness is vital, especially at the earliest stages of making a change. It’s worth it though, because as Callard says, what is really at stake is you are “learning to see the world in a new way.”
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.
However, this kind of digital inspiration is often only helpful at the beginning of the journey. Ultimately, you need to find people who are open to a deeper friendship and willing to spend meaningful time together.
On my previous path, there was a hidden cost to my success. The consistent financial rewards helped me live a smooth existence, needing to rely less on others the more I succeeded. In some circles, this is celebrated as the ultimate aim of life, but for me it led to a certain emptiness that I didn’t fully understand until I found myself on a path that forced me to find the others.
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?”
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.”75 This phrase helps me sit with my discomfort when I worry about my health.
To protect myself, I overcorrected and developed something my friend Visakan Veerasamy calls “preemptive defensiveness.” I saw myself in opposition to the world, seeing the simplest question as an attack on everything I stood for.
My parents had sacrificed so much for me and I felt selfish. Now
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.
This path offers profound personal growth, but its benefits often remain invisible to others.
“What will people think of me? I don’t even know what to think of me. Am I being completely irresponsible?
“will the people in your life love you less?” powerful because it addresses the scariest and deepest issues.
and had recently declared to my friends that I was giving up on dating and shifting to the “cool uncle” phase of my life.
Non-doing is not about escaping anything or being lazy but instead refers to a deep level of connectedness with the world.
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
“We must let go of the life we have planned, so as to accept the one that is waiting for us.”80
For most of my life, I had paired the idea of doing nothing with laziness.
I was able to embrace a state of doing nothing that was not filled with anxiety and tension, but reflective and open.
First, people become aware of their own suffering. Often we don’t notice our drift into a state of low‑grade anxiety until we step away from what causes it, as I noticed the first day after I quit my job and realized I was burned out.
‘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.”82
Second, curiosity re‑emerges. When people have time, they try new activities, revisit old hobbies, explore childhood curiosities, and start volunteering and connecting with people in their community.
Third, people often desire to continue their “non‑work” journey. Lenny Rachitsky, who took a sabbatical after a long career in product management, thought he would return to work,
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
Retirement was introduced in the late 1800s in Germany to provide support for the small number of people who survived to the age of 70 and could no longer work. Now people live longer and are healthier, so retirement is no longer rare, and in some countries, people are projected to spend up to one‑third of their life retired.
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. I’ve talked with many people in their 60s and 70s who actively reject the idea that they should stop working. While they often don’t have full‑time jobs, they enjoy working part‑time, volunteering, learning new things, or finding other ways to contribute.
The best approach I’ve found for figuring out how I want to live is Tim Ferriss’ idea of “mini‑retirements,” which he introduced in his book, The Four‑Hour Workweek.
After getting burned out on a short trip, he asked himself the question, “Why not take the usual 20–30‑year retirement and redistribute it throughout life instead of saving it all for the end?”88
How do your decisions change if retirement isn’t an option? What if you could use a mini‑retirement to sample your future plans now? Is it really necessary to commit fully to work to live like a millionaire?
I pick one or two things I want to prioritize and test. It might be living in a different type of place, working on new projects, traveling, or learning something new. My goal is to test my beliefs to get a better understanding of what really makes my life better.
The spirit of the mini‑retirement is not about escaping work. It is about testing different circumstances to see if you want to double down on them or change directions.
I was more than on my way to a magical retirement number but was also making great progress in undermining the spontaneity, creativity, and energy that would enable me to enjoy life once I got there. For me, testing out different ways of structuring my life now is a win‑win proposition. I’m lowering the odds that I’ll be unhappy in the future all while crafting a life I’m more and more excited to keep living.
cultures only learn and evolve when original approaches to living are discovered.
The secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours. — Amos Tversky
“What distinguishes the comfortable young men of today from the uncomfortable young men of the last hundred years…is that for once the younger generation is not in revolt against anything…We don’t want to rebel against our elders.94 The organizations that these young people joined offered predictable incomes and, most of all, predictable lives. Whyte saw this as a dramatic shift from the past because these organizations offered something that previous generations did not have, a safe haven from the real world, noting that “come graduation, they do not go outside to a hostile world; they
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No underlying logic justified my spending and a lot of it could be classified under what writer Thomas J. Bevan calls a “misery tax.” This is the spending an unhappy worker allocates to things that “keep you going and keep you functioning in the job.”96
Many people I talk to are convinced that the formula for living on their own terms is saving up enough money. I wish they knew what I know: the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is.
I still worry about money, success, belonging, and whether I can keep this journey going. However, I’m able to recognize that the right response is not to restructure my life to make these worries disappear. It’s to develop a capacity to sit with those anxieties, focus on what I can control, and to open myself up to the world.
about success. In response to the question, “How do you personally define success?”, 97% agreed with the following statement: A person is successful if they have followed their own interests and talents to become the best they can be at what they care about most. In response to the question, “How do you think others define success?”, only 8% gave the same answer. Instead, 92% felt that other people defined success as follows: A person is successful if they are rich, have a high-profile career, or are well‑known.100 Why the disconnect between how people define success and how we think others
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They default to “the heuristic of respecting the people who other people respect,”
Hitting #1 for the first time as an author felt like…nothing. Being a ‘millionaire’…nothing. It’s a trick of evolution that drives us, and no one is immune from making this mistake.”103 This is what Harvard professor Dr. Ben‑Shahar calls the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness.
The pathless path is a define-your-own-success adventure. In the first couple years, it felt silly to tell people how I defined success: feeling alive, helping people, and meeting my needs. Over time, I realized that the real benefit of this orientation towards success was that I wasn’t competing with anyone.
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.
I’m in an indie economy, where over the long‑term I’m competing on learning, developing skills, and my reputation. This is a lot harder but also a lot more rewarding.
I read William Deresiewicz’s essay, “The Disadvantages of An Elite Education.’’ His argument that elite schools often incentivize behaviors that undermine living a meaningful life
Nat Eliason, Anne-Laure Le Cunff, Pieter Levels, and Tiago Forte
This is why I’m fond of the advice angel investor Naval Ravikant offers, “play long‑term games with long‑term people.”
