The Pathless Path

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

Highlights

  • Study hard, get good grades, get a good job. Then put your head down and keep going, indefinitely. This is what I call the “default path.” (Location 89)
  • To Whyte, a pathless path is a paradox: “we cannot even see it is there, and we do not recognize it.”1 (Location 107)
  • 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)
  • One of the biggest things the pathless path did for me was to help me reimagine my relationship with work. When I left my job, I had a narrow view of work and wanted to escape. On the pathless path, my conception expanded, and I was able to see the truth: that most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them. (Location 121)
  • 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)
  • I’ve seen the shame of unexpected layoffs, the panic attacks from changing jobs, and the loss of hope people experience when they can’t make it work on the particular path they think they are supposed to follow. (Location 145)
  • With every new job, I convinced myself I was thriving. But what I was really doing was trying to escape feeling stuck. (Location 163)
  • Many people find it difficult to create change in their lives because they lack someone that believes in them. (Location 186)

2 Getting Ahead

  • 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 216)
  • However, the proliferation of paths presents a challenge. With so many options it can be tempting to pick a path that offers certainty rather than doing the harder work of figuring out what we really want. (Location 253)
  • prestige is “a powerful magnet that warps even your beliefs about what you enjoy.”12 (Location 261)
  • when we are faced with moments of undeniable awe and inspiration. (Location 351)
  • opportunity was exciting, but it enabled me to ignore those emerging cracks. I had loosened my attachment to “Paul as a successful person,” but was still firmly located in that successful world. (Location 407)

3 Work, Work, Work

  • If we are going to imagine a new way forward for our work and our lives, we need to understand where our current ideas from work come from and how they have changed. (Location 472)
  • 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)
  • 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 (Location 485)
  • In the 1500s, Martin Luther and John Calvin expanded this definition as part of what is now known as the Protestant Reformation. They had grown disappointed in religious leaders and attacked them for living idly in monasteries. Their angle of attack was one’s relationship to work. Max Weber summarizes the shift, saying that the way to honor God, “was not to surpass worldly morality in monastic asceticism, but solely through the fulfillment of the obligations imposed upon the individual by his position in the world. That was his calling.”22 (Location 499)
  • Working hard in the area of one’s calling determines the status of a person’s relationship with God. (Location 508)
  • “in the Northern European countries, from the 16th century on, man developed an obsessional craving to work which had been lacking in a free man before that period.” (Location 509)
  • The educated, hardworking masses are still doing what they’re told, but they’re no longer getting what they deserve. – Seth Godin (Location 535)
  • John Steinbeck captured the sentiment in his book America and Americans in 1966: No longer was it even acceptable that the child should be like his parents and live as they did; he must be better, live better, know more, dress more richly, and if possible, change from father’s trade to a profession. This dream became touchingly national. (Location 542)
  • In “Jobs, Careers, and Callings,” a famous study by Yale professor Amy Wrzesniewski and others, people were asked if they defined their work as a job, career, or a calling. (Location 578)
  • People who defined their work as a calling saw their work as “inseparable from their life” and worked, “not for financial gain or career advancement, but instead for the fulfillment that doing the work brings to the individual.” (Location 579)
  • In the 2010s the expectation that work should be meaningful became a default expectation of college graduates. (Location 597)

4 Awakening

  • 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 (Location 682)
  • My conclusion from this is simple: beyond the headlines of dramatic life changes are almost always longer, slower, and more interesting journeys. (Location 688)
  • Rather than participating in meetings as a good team member, I observed them as a visiting anthropologist. I saw my colleagues with 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? (Location 706)
  • 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. (Location 717)
  • The answer, my dear reader, is simple. You start underachieving at work. (Location 718)
  • Instead of being consumed with thoughts about work and my next step, I had time to continue to experiment, and in the space that emerged, a creative energy entered which started to become a central force in my life. (Location 723)
  • I split into two different versions of myself. One, “Default Path Paul,” focused on continuing my career, looking for the next job. The other, “Pathless Path Paul,’’ was finding his footing and starting to pay attention to the clues that were showing up. Clues that (Location 727)
  • would lead me not to another job, but to another life. (Location 729)
  • “Everything was going well and getting better. But despite all this, my motivation to go to work each morning was decreasing – almost in an inverse trend to my career and income growth.” (Location 760)
  • It took a year and a half for me to admit I did not enjoy my job. (Location 769)
  • 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 787)
  • My biggest barrier was my inability to imagine an alternative life. My creative experiments were exciting, but they didn’t suggest an obvious next step. (Location 789)
  • William Reilly’s book How To Avoid Work, (Location 791)
  • Making more money was not one of the priorities on the list I read on my phone every morning, so why was I so attached to what I thought I was worth? (Location 811)

5 Breaking Free

  • Second, I was struggling to think independently in a positive way. I was becoming cynical and confrontational rather than looking for ways to have a positive impact. (Location 834)
  • There was nothing special about those emails, but that day I couldn’t pretend to care about the latest client crisis. 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 847)
  • Now, without a plan and without anywhere to show up, I had to feel the full force of my emotions. (Location 892)
  • 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. (Location 898)
  • What if the value system of the institution is diametrically opposed to the values, ethics, and competencies of the individual professional? What if the individual professional seeks to live up to the external, organizationally imposed criteria of what constitutes success and achievement, but is unable to do (Location 906)
  • 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.” (Location 916)
  • Titled, “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. (Location 963)
  • 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. (Location 973)
  • we lived in a time of “total work,” a state of existence in which work is such a powerful force that almost everyone ends up identifying as a worker first and foremost. (Location 975)
  • He noted that the ancient Greek translation for “work” was literally “not‑at‑leisure.” In Aristotle’s own words, “we are not‑at‑leisure in order to be‑at‑leisure.” Now, this is flipped. We work to earn time off and see leisure as a break from work. (Location 982)
  • Are you a worker? If you are not a worker, then who are you? Given who you are, what life is sufficient? (Location 992)

6 The First Steps

Prototype Your Leap

  • I saw an article by author and designer John Zeratsky titled, “I Quit My Job to Sail Around Central America for 18 Months,” I knew immediately there was more. So I interviewed him for the podcast to find out just how he got to that point. (Location 1053)
  • His story started several years earlier. He said, “before we left…we would take small sailing trips, we would go somewhere for one night…Later that year we would do that for a long weekend, then for a week, and then for two weeks. A couple of years before we left on the ‘big trip’ we went for two months.”63 It took several years and many smaller trips to decide that sailing for more than a year was something they definitely wanted to do. (Location 1055)
  • This kind of approach, focused not on being brave, but instead on eliminating risk, is common for people who take unconventional paths. (Location 1059)
  • By experimenting with different ways of showing up in the world and making small, deliberate changes, we can open ourselves up to the unexpected opportunities, possibilities, and connections that might tell us what comes next. (Location 1085)
  • 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. (Location 1088)
  • We can explain this strategy with a simple equation: Uncertain Discomfort < Certain Discomfort + Coping Mechanism (Location 1091)
  • In other words, given sufficient coping strategies, people will be willing to tolerate consistent levels of misery for long stretches of time. (Location 1093)
  • Is there anything that can override this? In my conversations with people who have made changes in their life, one thing seems to work reliably: wonder. (Location 1094)
  • The equation becomes: Uncertain Discomfort + Wonder > Certain Discomfort (Location 1096)
  • In thoughts about the future, worry is traded for wonder. People stop thinking about worst‑case scenarios and begin to imagine the benefits of following an uncertain path. (Location 1098)
  • One challenge to embracing possibility is knowing when to override what psychology professors Gilovich and Davidai call our “‘ought to’ self.” (Location 1113)
  • “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.” (Location 1121)
  • 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)
  • You can leave the default path before facing your fears, but the pathless path forces you to reckon with them no matter what. I’ve come to see this as a benefit and I’ve shifted from someone that kept my fears buried beneath the surface to being aware of my fears and seeing them as tiny but manageable existential crises that are an inevitable part of an uncertain journey. (Location 1194)
  • In hundreds of conversations with people, I’ve found that these 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?” (Location 1198)
  • these fears overwhelmed me, but Tim Ferriss’ “fear setting” reflection exercise helped me reframe them and see fear in a completely new way.74 (Location 1202)
  • 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. (Location 1205)
  • However, some fear‑related problems cannot be solved. (Location 1209)
  • Reminding myself that this is a fact of life, like gravity, helps me accept the uncertainties of life and the pathless path. (Location 1213)
  • The final two questions of Ferriss’ exercise are the most powerful: 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? (Location 1214)
  • The most common regret? Not staying “true to themselves” in their lives and focusing too much on what others expected of them. (Location 1219)
  • People who value comfort and security often cannot understand why anyone would willingly pursue a path that increases discomfort and uncertainty. (Location 1242)
  • II The Pathless Path (Location 1254)

7 Wisdom of the Pathless Path

  • 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. (Location 1321)
  • no, it may have been worth it at one point, but not anymore.” (Location 1324)
  • 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. (Location 1331)
  • Third, people often desire to continue their “non‑work” journey. (Location 1336)
  • Fourth, people write. (Location 1341)
  • He described these as an “anti‑vacation” and “though it can be relaxing, the mini‑retirement is not an escape from your life but a reexamination of it—the creation of a blank slate.” (Location 1371)
  • How do your decisions change if retirement isn’t an option? (Location 1374)
  • What if you could use a mini‑retirement to sample your future plans now? (Location 1375)
  • Is it really necessary to commit fully to work to live like a millionaire? (Location 1376)
  • I try to think about time in blocks of one to three months and within each block, I pick one or two things I want to prioritize and test. (Location 1379)
  • On my previous path, 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. (Location 1388)
  • 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. (Location 1390)
  • I’m much more focused on spending time and money now to experiment with different modes of living such that when I reach the latter stages of my life, I won’t be making a dramatic shift in life priorities, but continuing on the pathless path. (Location 1393)
  • 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. (Location 1423)

Reimagine Money

  • When I left my job, I expected that working on my own would be challenging, but I did not expect my entire relationship to money and its role in my life to change. (Location 1444)
  • 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 For me, it was a mixture of alcohol, expensive food, and vacations, and as the amount inched up during my career, I started to believe that my spending was the reason I was working. (Location 1450)
  • “What is your rich life?” (Location 1455)
  • The purpose of this question is to stop you from looking at money as an accountant and looking at it as something that might help you live your ideal life. Over (Location 1456)
  • Once we know, as Vicky Robin argues in her book Your Money or Your Life, that “money is something we choose to trade our life energy for,” it is nearly impossible to give up your time for money without thinking deeply about the trade-offs.97 (Location 1469)
  • 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. (Location 1492)
  • 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. (Location 1494)

8 Redefine Success

  • 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.104 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 1544)
  • Are you helping people? Are they happy? Are you happy? Are you profitable? Isn’t that enough? – Derek Sivers (Location 1726)

9 The Real Work of Your Life

  • While the pathless path is a solo journey, it is important that you have at least one close friend with whom you can have these kinds of intimate conversations. (Location 1870)

Design for Liking Work

  • Ghost still does not employ a single employee that works with enterprise customers. 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. (Location 1893)
  • 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)
  • 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. (Location 1901)
  • am consciously pursuing a life designed around doing work I like (Location 1942)
  • According to Robert Kegan, a psychologist at Harvard, we are shifting away from a world where we need to fit in towards one where we must develop the skill of “self‑authoring.” (Location 1950)
  • 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. (Location 1953)
  • “humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.” (Location 1975)
  • Seth Godin puts it bluntly: “The world just gave you control over the means of production. Not to master them is a sin.” (Location 2021)
  • Figuring out who you want to serve is an important element of the pathless path. On the default path, your job often provides recognition and praise. When you are on your own, without a specific job or colleagues, you may miss that kind of support. (Location 2067)
  • This is why it’s so important to know what kind of people you want to work with and who you want to serve. Finding the right people, those who might offer support and encouragement along the way can have an outsized effect on your confidence and courage to keep going. (Location 2069)
  • You can experiment with your work and your life until you stumble into a virtuous cycle that helps you continue to move in a positive direction. (Location 2151)
  • By a virtuous cycle, I mean being able to do work that you enjoy that naturally leads to opportunities and people that help make your life better. (Location 2151)
  • The biggest challenge to creating your virtuous cycle and one of the most dangerous failure modes of the pathless path is cynicism. (Location 2153)
  • Many people who leave the default path do so because they’ve become cynical and are driven by a desire to escape. (Location 2154)

10 Playing the Long Game

  • But I am not nuts. I am happy. I am successful on my own terms. Because if your success is not on your own terms, if it looks good to the world but does not feel good in your heart, it is not success at all. – Anna Quindlen (Location 2162)
  • One of the goals of the pathless path is to make commitments: to a type of work, ways of living, creative projects, or a “conversation” with the world. (Location 2165)
  • how do you begin to figure out what you want to do when there are not many limits? (Location 2167)
  • instead of asking what makes up an amazing life, we first define the worst‑case scenario and then work backward. What does a miserable life entail? What actions would make achieving such a life more likely? Then figure out how you can avoid these things from becoming true. (Location 2177)
  • I encourage everyone to write a description of the person you don’t want to be, then brainstorm actions that might create that outcome. This exercise may be uncomfortable because undoubtedly you will see traces of the person you imagine in your present life. These traces are clues about what to change in your life right now. (Location 2193)
  • In addition to identifying who we don’t want to become, we should seek to identify ways of working and living that might add unnecessary risk to our path. (Location 2196)
  • Early in my journey, I identified being a freelancer and having a single type of income as a key risk. This motivated me to try to make money in as many ways as possible, even if it meant sacrificing short‑term income to do so. (Location 2197)
  • Like a city with many industries, I want to be resilient to changes in income, shifts in the economy, and rule changes from various platforms that I use. (Location 2201)
  • Early on in my journey, I realized that my entire goal was to stay on the pathless path indefinitely. This is what author James Carse calls the “infinite game”: “A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play. (Location 2206)
  • By working backward, I realized that the biggest risks for me are spending my time doing things that undermine my ability to stay optimistic and energized, and obviously, running out of money. (Location 2209)
  • People come to realize that the challenge is not to find work to pay the bills but instead to have time to keep taking chances and exploring opportunities to find the things worth committing to over the long-term. (Location 2213)
  • Fromm argued that those freed from oppression but unable to develop a positive version of freedom were destined to be filled with feelings of separateness and anxiety.154 (Location 2234)
  • 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.156 (Location 2250)
  • Wallace’s point is that doing what almost everyone else is doing is the natural thing in life. If we are serious about other approaches, it will take work. (Location 2254)
  • Professor and author Yuval Harari argued that “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.” (Location 2308)
  • Everyone on the pathless path eventually needs to develop a strategy for approaching their journey. (Location 2424)
  • To prioritize, developing a set of principles to help you make decisions is essential. (Location 2426)
  • One of my most important is the mantra “coming alive over getting ahead.” I embraced this fundamental shift when I left my previous path, and the mantra reminds me that I don’t want to create another job for myself. (Location 2429)
  • Before committing, I spent a couple of days reflecting on the decision, asking myself, “What would I end up doing with the increased earnings?” I decided I would use the time to write. Then I realized that there was nothing stopping me from doing that at that moment. So I decided that instead of scaling my course, I would write this book. (Location 2439)
  • At many steps along the journey, when I see an opportunity to make more money or pursue something that would require me to scale beyond a “company of one,” I pause. I spent ten years on a path where making numbers go up was always the way forward. (Location 2445)
  • “I traded lots of dreams for a bigger paycheck, and I never even realized I was doing it.” (Location 2471)
  • the concept of culture is pretty straightforward. It consists of an evolving set of assumptions that people use to make decisions. And the result of those actions is what shapes the culture. (Location 2512)
  • To create your own culture on the pathless path you must identify the assumptions you make in your approach to life. (Location 2513)
  • Here are some of my assumptions, many of which have been sprinkled throughout this book: (Location 2514)
  • Many people are capable of more than they believe. Creativity is a real path to optimism, meaning, and connection. We don’t need permission to engage with the world and people around us. We are all creative, and it takes some people longer to figure that out. Leisure, or active contemplation, is one of the most important things in life, There are many ways to make money, and when an obvious path emerges, there is often a more interesting path not showing itself. Finding the work that matters to us is the real work of our lives. (Location 2515)
  • After reading this book, you should no longer be able to look at your current path and think, “this is definitely the only way.” Instead, I hope you are able to shift to a place where you know that you have more freedom than you think, and your path can become something you choose again every day. (Location 2535)
  • You must be a little crazy to go against the grain of what most people think. Yet we should remind ourselves that these “experiments in living” as John Stuart Mill called them, are vital to pushing culture forward. (Location 2546)
  • First, question the default. For many years, I stuck with a story about how I thought my life should go. I assumed there was only one option for structuring my life, around full-time work. (Location 2553)
  • Second, reflect. When I started reflecting on my true self, I was able to start building a life around the things I valued. (Location 2557)
  • Third, figure out what you have to offer. In our desire to be successful, we forget to notice how we are having an impact on others. One of the easiest ways to begin this exploration is to send a message to a few close… (Location 2561)
  • Fourth, pause and disconnect. To improve your relationship with work, I believe it is necessary to disconnect. Unfortunately, a typical one or two-week vacation isn’t going to cut it. I believe that the… (Location 2565)
  • Fifth, go make a friend. Venture out of your existing bubble and reach out to someone who has taken an interesting path. Ask them how they got started, what motivates them,… (Location 2570)
  • Over time, designing your work in a way that will help you naturally “find the others,” can be one of the most rewarding things of being on the pathless path and one of… (Location 2573)
  • Sixth, go make something. Remember, you are creative! Almost everyone has a desire to create something and to put their energy into the world in a positive way. It’s just that the legacy of the default path has convinced people that they need… (Location 2574)
  • Seventh, give generously. Generosity is not only an amount of money, it is a skill we need to practice. It is a way of orienting towards the world that will help you start to understand your own definition of “enough,” grapple with your hidden money scripts, and enable you… (Location 2579)
  • Eighth, experiment. The default path does not leave much space for experimenting with different ways of structuring your life. On the pathless path, you can prototype a change, work in different ways, take extended breaks, live in different countries, test your money beliefs, embrace unique fixed-point goals, and create things you never thought were… (Location 2585)
  • Ninth, commit. Many people falsely think that escaping work is something worth aiming towards. I thought this at first but realized I had only thought about work as the things you do within a job. What I really wanted was the opportunity… (Location 2588)
  • Finally, be patient. In a famous letter to his friend Hume, Hunter S. Thompson argued that searching for the right path in life was important, even… (Location 2592)
  • It took me years to build up the courage to quit my job and then several more years to find a mix of work, people, and a way of orienting in the world that felt… (Location 2596)