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The Pathless Path

The Pathless Path

Metadata

  • Author: Paul Millerd
  • Full Title: The Pathless Path
  • Category: #books

Highlights

  • 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. (Location 97)
  • My restlessness was easy to hide because my path was filled with impressive names and achievements, and when you’re on such a path, no one asks “Why are you doing this?” (Location 100)
  • About a year into this journey, I stumbled upon a phrase which helped me take a deep breath. It was the idea of a “pathless path,” something I found in David Whyte’s book The Three Marriages. To Whyte, a pathless path is a paradox: “we cannot even see it is there, and we do not recognize it.”1 To me, the pathless path was a mantra to reassure myself I would be okay. (Location 106)
  • 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. (Location 112)
  • 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. Along the way, I learned how to play the game of success and achievement, but never paused to find out what I really wanted. (Location 125)
  • Researchers Dorthe Berntsen and David Rubin study what they call “life scripts,” which they describe as “culturally shared expectations as to the order and timing of life events in a prototypical life course.” (Location 132)
    • Note: Look into
  • 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. (Location 137)
  • the particular path they think they are supposed to follow. On top of that, people are ashamed to talk about these things with the people in their lives. (Location 146)
  • 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. (Location 159)
  • With every new job, I convinced myself I was thriving. But what I was really doing was trying to escape feeling stuck. (Location 163)
  • 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 (Location 199)
  • They embodied a success ethic that focused on maximizing achievements in the present to create better options in the future. I started to resent the high school I had attended, where the guidance counselor suggested I try a major other than engineering because “it was hard.” Why hadn’t people pushed me harder? Should I have applied to better schools? (Location 215)
  • “the desire for security and the feeling of insecurity are the same thing,” (Location 265)
  • I wasn’t picky about the type of work I’d be doing, I just wanted it to be seen as impressive. (Location 275)
  • My unease quickly morphed into a desire to escape. When I joined, GE was a 100‑year‑old company with a great reputation but was starting to show its age. I couldn’t imagine spending the rest of my career there, let alone two years. No one seemed to care about anything. (Location 309)
  • 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.” (Location 331)
  • 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. (Location 339)
  • 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.” (Location 340)
  • 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. (Location 347)
  • 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. (Location 372)
  • The truth was that my experience of the illness was changing me and there would be no going back. (Location 454)
  • 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.”17 (Location 461)
  • 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. (Location 476)
  • 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.”26 (Location 526)
  • The mistake we made was thinking that the period from 1946 to 1980 was the norm. No, it was not! It was the anomaly! We had just wiped out the manufacturing capabilities of anyone who could challenge us. So, the idea that you had that job with the gold watch, and you could work there for your entire career and raise a family of four and all of that, that was an anomaly.30 (Location 555)
  • The notion of spending the rest of my life doing mindless busywork horrified me and motivated me to keep searching for better options. (Location 671)
  • 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. (Location 682)
  • 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.” (Location 693)
  • My final list included four items: health, relationships, fun & creativity, and career. Since 2013, this list pops up on my phone at 8:30 a.m. each morning. (Location 715)
  • The answer, my dear reader, is simple. You start underachieving at work. (Location 718)
  • You stop setting an alarm and you cancel morning meetings because the energy gained is worth fighting for. You start working remotely on Fridays without asking because the extra 24 hours with your grandmother is worth it. You start taking naps at the office because there’s a nap room and someone has to use it, right? (Location 719)
  • From my perspective now, I had no future at the company, and by the time I had that conversation about my performance with my manager, things were already headed south. Yet I was still working hard on my proposal for promotion, outlining a multi‑year career path for my position. Based on the experiences of others who leave the default path, this stage of contradiction is common. You take a last stand, doubling down on the existing path despite all evidence that it is no longer working. (Location 785)
    • Note: Me at manyone
  • 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 (Location 791)
  • These questions inspired an idea: what if I paired making less with working less? (Location 821)
  • 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 (Location 825)
  • Jerry Colonna, an investor turned executive coach, asks his clients this question, “How are you complicit in creating the conditions you say you don’t want?” (Location 839)
  • Anyone who has worked in client or customer‑facing jobs knows that the work mostly focuses on reacting to ongoing mini‑crises. Almost everyone agrees that these issues are not all that important, but almost no one can stop themselves from reacting to each one with equal enthusiasm and panic. (Location 848)
  • I told myself I was smarter than other people. I knew what I was good at. I always took all of my vacation days. Didn’t work crazy hours. Made time for friends and family. Changed jobs when I stopped learning. I had done all these things with the idea that this was how I would not only avoid burning out but that I would thrive. I wanted to hack the system and make it work for me. On my final day of work the feelings that flowed through my body told me I wasn’t so clever. (Location 882)
  • He found that the prime candidates for burnout were those who were “dedicated and committed,” trying to balance their need to give, to please others, and to work hard. He noticed that when there was added pressure from superiors, people often hit a breaking point.52 (Location 898)
  • “the bureaucratic infringement on a professional’s autonomy” (Location 903)
  • As I was booking the flights, I initially typed in dates two weeks apart, but then realized I had no obligations to return to. Before this trip, I had never traveled anywhere for more than two weeks. As I extended the dates to five weeks on the booking app, sirens sounded in my head. This was the first of many experiences in which I pushed past the default setting of how I was supposed to be living. (Location 926)
  • Professor Freudenberger noted in his research that 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.” (Location 932)
  • Are you a worker? If you are not a worker, then who are you? Given who you are, what life is sufficient? (Location 992)
  • 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.” (Location 994)
  • This kind of approach, focused not on being brave, but instead on eliminating risk, is common for people who take unconventional paths. I hadn’t set out to prototype a life beyond full‑time work, but through freelance projects, coaching, paid speaking, writing, and connecting with people online, I achieved the same result. I knew what it felt like to work “differently” and make money on my own, and I learned to appreciate the “spirit of the fool” on an uncertain path. This was powerful because it helped me expand my perception of what I thought possible. (Location 1059)
  • In thoughts about the future, worry is traded for wonder. (Location 1098)
  • 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. (Location 1136)
  • 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. (Location 1155)
  • 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?” (Location 1199)
  • many people will override their own desires to meet the perceived expectations of others, such as a spouse or parent. (Location 1227)
  • To protect myself, I overcorrected and developed something my friend Visakan Veerasamy calls “preemptive defensiveness.” (Location 1230)
  • 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. (Location 1240)
  • So I might add to Steinbeck’s advice: nothing good gets away, as long as you create the space to let it emerge. (Location 1301)
  • 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 (Location 1349)
  • 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. (Location 1352)
  • 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. (Location 1363)
  • What if you could use a mini‑retirement to sample your future plans now? (Location 1375)
  • When I started writing this book, I was studying Chinese thirty hours per week and running my online business. It was intense. It’s not something I want to do year‑round, but these intense periods of learning, creativity, and work followed by periods of rest provide a sustainable and energizing way to stay on this path over the long term. This kind of variability is hard to design into your life on the default path. (Location 1384)
  • fixed point is a non‑negotiable goal that you plan to achieve, no matter what. These fixed points are often a product of our unique cultural scripts. (Location 1396)
  • We all have fixed points that we aim towards in our lives. Homeownership is one of the most popular, but others include paying for children’s college expenses, becoming an executive or partner, founding a company, or reaching a certain net worth. (Location 1400)
  • Rao argues that the answer is not to abandon goals altogether but to take them more seriously and to put more thought into identifying unique fixed points, ones that align with the things that bring us alive. (Location 1407)
  • Mill argued that conventional ways of living tend to “degenerate into the mechanical’’ and that if societal norms are too strong or rigid, original thinkers who would otherwise experiment will be stifled. (Location 1414)
  • Right now, I’m orienting my work around taking every seventh week off from work no matter what. This was inspired by tech entrepreneur Sean McCabe, who adopted the policy for himself and eventually, his entire company.93 The fixed (Location 1423)
  • 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 (Location 1431)
  • 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.” (Location 1449)
  • the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness. (Location 1545)
  • When we realize that this isn’t the case, we find ourselves feeling empty, and the easiest way to deal with this is to ignore the feeling and ratchet up the goal. (Location 1547)
  • I was being granted special status in a “prestige economy” that, as the writer Sarah Kendzior argues, places “money over merit, brand over skill.”109 (Location 1583)
  • The way you get lots of users is to make the product really great. (Location 1593)
  • I don’t think I realized how much I hated this until I became self‑employed and immediately stopped spending any time hacking tests. (Location 1599)
  • Working on my own, I’m no longer in Kendzior’s prestige economy where brand is more important than skill. 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. (Location 1603)
  • gaslight themselves by starting off their own complaints with, “I know I should be grateful, but…”. (Location 1612)
  • People like Nat Eliason, Anne-Laure Le Cunff, Pieter Levels, and Tiago Forte (Location 1632)
  • This is why I’m fond of the advice angel investor Naval Ravikant offers, “play long‑term games with long‑term people.” (Location 1652)
  • In his book Seeing Like a State, James Scott argues that “legibility” made modernity possible. By legibility, he means “arranging the population in ways that simplified the classic state functions of taxation, conscription, and prevention of rebellion.”114 (Location 1659)
  • “Good” eggs are those that meet specifications, are perfectly clean, and can legally be sold in a supermarket. (Location 1674)
  • A Field Guide To Getting Lost. She says that, “losing things is about the familiar falling away,” but “getting lost is about the unfamiliar appearing.”122 (Location 1711)
  • 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 lives without excess.125 (Location 1738)
  • Writer Jocelyn Glei, who worked at a startup, noted, “After being at a startup for four years and getting the chance to make tons of cool stuff, I was intoxicated with my own productivity. I got wildly ambitious and decided to 3x my workload, adding multiple massive new projects (of my own devising!) to an already intensive work schedule.” It (Location 1748)
  • Enough is knowing that no amount in my bank account will ever satisfy my deepest fears. It’s knowing that I have enough friends that would gladly open their door and share a meal if I was ever in need. It’s the feeling that I’ve been able to spend my time over an extended stretch of time working on projects that are meaningful to me, helping people with a spirit of generosity, and having enough space and time in my life to stay energized to keep doing this over the long‑term. Enough is seeing a clear opportunity that will increase my earnings in the short‑term, but knowing that saying “no” will open me up to things that might be even more valuable in ways that are hard to understand. Enough is knowing that the clothes, fancy meal, or latest gadget will not make me happier, but also that buying such things won’t mean I’m going to end up broke. Enough is having meaningful conversations with people that inspire me, people that I love, or people that support me. (Location 1758)
  • The researchers concluded that when we feel we lack something, we tend to obsess over it. (Location 1797)
  • He argues that “if everyone honestly admitted his urge to be a hero it would be a devastating release of truth.”129 (Location 1810)
  • “It’s astonishing how much time human beings spend away from that frontier.” (Location 1843)
  • In my favorite essay, “Solitude and Leadership,” William Deresiewicz highlights the importance of searching for wisdom in real conversations with close friends: 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 (Location 1864)
  • 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. (Location 1898)
  • Unfortunately, this life was built around freelancing and my heart was never in it. I still enjoy working on some consulting projects, but it’s not what drives me. (Location 1907)
  • shame as “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging.” She believes that most people give too much power to this emotion when making life choices.”138 (Location 1958)
  • trapped in a pseudo‑freedom where one is free from absolute oppression but not free enough to act with a high degree of agency. (Location 2277)

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title: The Pathless Path longtitle: The Pathless Path author: Paul Millerd url: , source: kindle last_highlight: 2022-08-12 type: books tags:

The Pathless Path

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Metadata

  • Author: Paul Millerd
  • Full Title: The Pathless Path
  • Category: #books

Highlights

  • 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. (Location 97)
  • My restlessness was easy to hide because my path was filled with impressive names and achievements, and when you’re on such a path, no one asks “Why are you doing this?” (Location 100)
  • About a year into this journey, I stumbled upon a phrase which helped me take a deep breath. It was the idea of a “pathless path,” something I found in David Whyte’s book The Three Marriages. To Whyte, a pathless path is a paradox: “we cannot even see it is there, and we do not recognize it.”1 To me, the pathless path was a mantra to reassure myself I would be okay. (Location 106)
  • 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. (Location 112)
  • 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. Along the way, I learned how to play the game of success and achievement, but never paused to find out what I really wanted. (Location 125)
  • Researchers Dorthe Berntsen and David Rubin study what they call “life scripts,” which they describe as “culturally shared expectations as to the order and timing of life events in a prototypical life course.” (Location 132)
    • Note: Look into
  • 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. (Location 137)
  • the particular path they think they are supposed to follow. On top of that, people are ashamed to talk about these things with the people in their lives. (Location 146)
  • 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. (Location 159)
  • With every new job, I convinced myself I was thriving. But what I was really doing was trying to escape feeling stuck. (Location 163)
  • 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 (Location 199)
  • They embodied a success ethic that focused on maximizing achievements in the present to create better options in the future. I started to resent the high school I had attended, where the guidance counselor suggested I try a major other than engineering because “it was hard.” Why hadn’t people pushed me harder? Should I have applied to better schools? (Location 215)
  • “the desire for security and the feeling of insecurity are the same thing,” (Location 265)
  • I wasn’t picky about the type of work I’d be doing, I just wanted it to be seen as impressive. (Location 275)
  • My unease quickly morphed into a desire to escape. When I joined, GE was a 100‑year‑old company with a great reputation but was starting to show its age. I couldn’t imagine spending the rest of my career there, let alone two years. No one seemed to care about anything. (Location 309)
  • 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.” (Location 331)
  • 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. (Location 339)
  • 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.” (Location 340)
  • 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. (Location 347)
  • 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. (Location 372)
  • The truth was that my experience of the illness was changing me and there would be no going back. (Location 454)
  • 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.”17 (Location 461)
  • 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. (Location 476)
  • 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.”26 (Location 526)
  • The mistake we made was thinking that the period from 1946 to 1980 was the norm. No, it was not! It was the anomaly! We had just wiped out the manufacturing capabilities of anyone who could challenge us. So, the idea that you had that job with the gold watch, and you could work there for your entire career and raise a family of four and all of that, that was an anomaly.30 (Location 555)
  • The notion of spending the rest of my life doing mindless busywork horrified me and motivated me to keep searching for better options. (Location 671)
  • 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. (Location 682)
  • 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.” (Location 693)
  • My final list included four items: health, relationships, fun & creativity, and career. Since 2013, this list pops up on my phone at 8:30 a.m. each morning. (Location 715)
  • The answer, my dear reader, is simple. You start underachieving at work. (Location 718)
  • You stop setting an alarm and you cancel morning meetings because the energy gained is worth fighting for. You start working remotely on Fridays without asking because the extra 24 hours with your grandmother is worth it. You start taking naps at the office because there’s a nap room and someone has to use it, right? (Location 719)
  • From my perspective now, I had no future at the company, and by the time I had that conversation about my performance with my manager, things were already headed south. Yet I was still working hard on my proposal for promotion, outlining a multi‑year career path for my position. Based on the experiences of others who leave the default path, this stage of contradiction is common. You take a last stand, doubling down on the existing path despite all evidence that it is no longer working. (Location 785)
    • Note: Me at manyone
  • 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 (Location 791)
  • These questions inspired an idea: what if I paired making less with working less? (Location 821)
  • 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 (Location 825)
  • Jerry Colonna, an investor turned executive coach, asks his clients this question, “How are you complicit in creating the conditions you say you don’t want?” (Location 839)
  • Anyone who has worked in client or customer‑facing jobs knows that the work mostly focuses on reacting to ongoing mini‑crises. Almost everyone agrees that these issues are not all that important, but almost no one can stop themselves from reacting to each one with equal enthusiasm and panic. (Location 848)
  • I told myself I was smarter than other people. I knew what I was good at. I always took all of my vacation days. Didn’t work crazy hours. Made time for friends and family. Changed jobs when I stopped learning. I had done all these things with the idea that this was how I would not only avoid burning out but that I would thrive. I wanted to hack the system and make it work for me. On my final day of work the feelings that flowed through my body told me I wasn’t so clever. (Location 882)
  • He found that the prime candidates for burnout were those who were “dedicated and committed,” trying to balance their need to give, to please others, and to work hard. He noticed that when there was added pressure from superiors, people often hit a breaking point.52 (Location 898)
  • “the bureaucratic infringement on a professional’s autonomy” (Location 903)
  • As I was booking the flights, I initially typed in dates two weeks apart, but then realized I had no obligations to return to. Before this trip, I had never traveled anywhere for more than two weeks. As I extended the dates to five weeks on the booking app, sirens sounded in my head. This was the first of many experiences in which I pushed past the default setting of how I was supposed to be living. (Location 926)
  • Professor Freudenberger noted in his research that 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.” (Location 932)
  • Are you a worker? If you are not a worker, then who are you? Given who you are, what life is sufficient? (Location 992)
  • 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.” (Location 994)
  • This kind of approach, focused not on being brave, but instead on eliminating risk, is common for people who take unconventional paths. I hadn’t set out to prototype a life beyond full‑time work, but through freelance projects, coaching, paid speaking, writing, and connecting with people online, I achieved the same result. I knew what it felt like to work “differently” and make money on my own, and I learned to appreciate the “spirit of the fool” on an uncertain path. This was powerful because it helped me expand my perception of what I thought possible. (Location 1059)
  • In thoughts about the future, worry is traded for wonder. (Location 1098)
  • 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. (Location 1136)
  • 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. (Location 1155)
  • 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?” (Location 1199)
  • many people will override their own desires to meet the perceived expectations of others, such as a spouse or parent. (Location 1227)
  • To protect myself, I overcorrected and developed something my friend Visakan Veerasamy calls “preemptive defensiveness.” (Location 1230)
  • 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. (Location 1240)
  • So I might add to Steinbeck’s advice: nothing good gets away, as long as you create the space to let it emerge. (Location 1301)
  • 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 (Location 1349)
  • 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. (Location 1352)
  • 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. (Location 1363)
  • What if you could use a mini‑retirement to sample your future plans now? (Location 1375)
  • When I started writing this book, I was studying Chinese thirty hours per week and running my online business. It was intense. It’s not something I want to do year‑round, but these intense periods of learning, creativity, and work followed by periods of rest provide a sustainable and energizing way to stay on this path over the long term. This kind of variability is hard to design into your life on the default path. (Location 1384)
  • fixed point is a non‑negotiable goal that you plan to achieve, no matter what. These fixed points are often a product of our unique cultural scripts. (Location 1396)
  • We all have fixed points that we aim towards in our lives. Homeownership is one of the most popular, but others include paying for children’s college expenses, becoming an executive or partner, founding a company, or reaching a certain net worth. (Location 1400)
  • Rao argues that the answer is not to abandon goals altogether but to take them more seriously and to put more thought into identifying unique fixed points, ones that align with the things that bring us alive. (Location 1407)
  • Mill argued that conventional ways of living tend to “degenerate into the mechanical’’ and that if societal norms are too strong or rigid, original thinkers who would otherwise experiment will be stifled. (Location 1414)
  • Right now, I’m orienting my work around taking every seventh week off from work no matter what. This was inspired by tech entrepreneur Sean McCabe, who adopted the policy for himself and eventually, his entire company.93 The fixed (Location 1423)
  • 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 (Location 1431)
  • 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.” (Location 1449)
  • the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness. (Location 1545)
  • When we realize that this isn’t the case, we find ourselves feeling empty, and the easiest way to deal with this is to ignore the feeling and ratchet up the goal. (Location 1547)
  • I was being granted special status in a “prestige economy” that, as the writer Sarah Kendzior argues, places “money over merit, brand over skill.”109 (Location 1583)
  • The way you get lots of users is to make the product really great. (Location 1593)
  • I don’t think I realized how much I hated this until I became self‑employed and immediately stopped spending any time hacking tests. (Location 1599)
  • Working on my own, I’m no longer in Kendzior’s prestige economy where brand is more important than skill. 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. (Location 1603)
  • gaslight themselves by starting off their own complaints with, “I know I should be grateful, but…”. (Location 1612)
  • People like Nat Eliason, Anne-Laure Le Cunff, Pieter Levels, and Tiago Forte (Location 1632)
  • This is why I’m fond of the advice angel investor Naval Ravikant offers, “play long‑term games with long‑term people.” (Location 1652)
  • In his book Seeing Like a State, James Scott argues that “legibility” made modernity possible. By legibility, he means “arranging the population in ways that simplified the classic state functions of taxation, conscription, and prevention of rebellion.”114 (Location 1659)
  • “Good” eggs are those that meet specifications, are perfectly clean, and can legally be sold in a supermarket. (Location 1674)
  • A Field Guide To Getting Lost. She says that, “losing things is about the familiar falling away,” but “getting lost is about the unfamiliar appearing.”122 (Location 1711)
  • 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 lives without excess.125 (Location 1738)
  • Writer Jocelyn Glei, who worked at a startup, noted, “After being at a startup for four years and getting the chance to make tons of cool stuff, I was intoxicated with my own productivity. I got wildly ambitious and decided to 3x my workload, adding multiple massive new projects (of my own devising!) to an already intensive work schedule.” It (Location 1748)
  • Enough is knowing that no amount in my bank account will ever satisfy my deepest fears. It’s knowing that I have enough friends that would gladly open their door and share a meal if I was ever in need. It’s the feeling that I’ve been able to spend my time over an extended stretch of time working on projects that are meaningful to me, helping people with a spirit of generosity, and having enough space and time in my life to stay energized to keep doing this over the long‑term. Enough is seeing a clear opportunity that will increase my earnings in the short‑term, but knowing that saying “no” will open me up to things that might be even more valuable in ways that are hard to understand. Enough is knowing that the clothes, fancy meal, or latest gadget will not make me happier, but also that buying such things won’t mean I’m going to end up broke. Enough is having meaningful conversations with people that inspire me, people that I love, or people that support me. (Location 1758)
  • The researchers concluded that when we feel we lack something, we tend to obsess over it. (Location 1797)
  • He argues that “if everyone honestly admitted his urge to be a hero it would be a devastating release of truth.”129 (Location 1810)
  • “It’s astonishing how much time human beings spend away from that frontier.” (Location 1843)
  • In my favorite essay, “Solitude and Leadership,” William Deresiewicz highlights the importance of searching for wisdom in real conversations with close friends: 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 (Location 1864)
  • 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. (Location 1898)
  • Unfortunately, this life was built around freelancing and my heart was never in it. I still enjoy working on some consulting projects, but it’s not what drives me. (Location 1907)
  • shame as “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging.” She believes that most people give too much power to this emotion when making life choices.”138 (Location 1958)
  • trapped in a pseudo‑freedom where one is free from absolute oppression but not free enough to act with a high degree of agency. (Location 2277)