The Pathless Path

Metadata

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

Highlights

• 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 113)
• am inspired by what the writer Leo Rosten once argued was the purpose of life: “to be useful, to be honorable, to be compassionate, to have it make some difference that you have lived and lived well.”6 (Location 189)
• No one wanted to grapple with this fundamental question: “Why the hell are so many grown adults spending their time on obviously pointless tasks?” (Location 668)
• Staring at those four items, in that order, was scary. 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)
• 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. (Location 793)
• 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.”55 Freudenberger argued that recovering from burnout involves a grieving process to let go of those ideals. (Location 933)
• Pieper argued that for most of history, leisure was one of the most important parts of life for people in many cultures. 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. Pieper pointed out that people “mistake leisure for idleness, and work for creativity.” To Pieper, leisure was above work. It was “a condition of the soul,” and the “disposition of receptive understanding, of contemplative beholding, and immersion–in the real.”57 (Location 982)
• Aspirational pursuits go hand in hand with the pathless path because they can appear incomprehensible to others and even yourself, sometimes for years. Callard argues that the aspirant’s understanding of the value of their pursuits “is characterized by a distinctive kind of vagueness, one she experiences as defective and in need of remedy.”71 (Location 1150)
• 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.” (Location 1154)
• 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. (Location 1241)
• I was also 33 years old, single, and had recently declared to my friends that I was giving up on dating and shifting to the “cool uncle” phase of my life. (Location 1270)
• That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.77 (Location 1274)
• I now agree with Joseph Campbell, who through his study of the human experience through our ancestors’ stories, concluded that “We must let go of the life we have planned, so as to accept the one that is waiting for us.”80 So I might add to Steinbeck’s advice: nothing good gets away, as long as you create the space to let it emerge. (Location 1299)
• In Taiwan, I was able to embrace a state of doing nothing that was not filled with anxiety and tension, but reflective and open. The possibilities that started to emerge at this time have changed my life. After more than three decades of constantly planning for the future, I was able to start living in the present. (Location 1306)
• With this mindset, he designed his own mini‐retirements, trips of “one to six months” where he would test out living in different ways. 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.”89 While designing these breaks into his life he asked himself three questions: 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? (Location 1371)
• 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. 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. On the pathless path not only is it possible, but it can be one of the most rewarding benefits. (Location 1383)
• 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. (Location 1390)
• In his book, On Liberty, published in 1859, John Stuart Mill was giving similar advice, arguing that societies need people to embrace their individuality and perform “experiments in living.” He argued that such experiments are vital to the pursuit of knowledge and that cultures only learn and evolve when original approaches to living are discovered. Mill wanted people to act on their inspiration because “the worth of different modes of life should be proved practically when anyone thinks fit to try them.”91 By choosing a unique and personal fixed point, in Mill’s view, you are not only raising the odds of finding a path worth staying on, but you are also serving an important role in pushing culture forward. (Location 1409)
• 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. He argues that trying to constrain these people is also not worth doing because they already struggle, “fitting themselves, without hurtful compression, into any of the small number of molds which society provides.”92 (Location 1416)
• With money coming in and a lower cost of living, my financial insecurity decreased, leading to a chain reaction in my understanding of work. If I wasn’t working for money, why was I working? When we work full‐time, employers are paying for our dedication and commitment to the job as a central part of our life. When I became self‐employed, I was disoriented because the people paying me for the projects didn’t care when and how much I worked. They just wanted their problems solved. It was up to me to figure out how to spend my time. (Location 1462)
• Having faith is admitting that you don’t have all the answers for what comes next. Another phrase I’ve found useful to describe this state of mind is what the spiritual teacher Tara Brach calls “radical acceptance,” which she says “is the willingness to experience ourselves and our lives as it is.” (Location 1487)
• As the spiritual teacher Sharon Salzberg has written, “whatever takes us to our edge, to our outer limits, leads us to the heart of life’s mystery, and there we find faith.”99 This is the essence of the pathless path, and the only way to develop room for faith in your life is to do exactly as Salzberg says, explore the limits and step into the possibilities for our life. The fact that the next steps are unknown to us is exactly the point. (Location 1499)
• The better way is what I call the “second chapter of success” in which you shift your mindset from what you lack to what you have to offer, from ambition to aspiration, and from hoping that joy will result from a specific outcome to experiencing it as a byproduct of your journey. (Location 1559)
• 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. This meant that the odds of success were incredibly high and the benefits of staying on the pathless path would only compound and increase over time. (Location 1568)
• The world is changing and the pathless path is just one way to exit the world of bad tests. As more and more people decide that these tests are silly, we can create new and better games. Ones that aren’t optimized for how employers like to see the world, but rather align with how we are motivated to learn and grow through our lives. I think this really matters and I agree with Graham’s assessment: “This is not just a lesson for individuals to unlearn, but one for society to unlearn, and we’ll be amazed at the energy that’s liberated when we do.”112 (Location 1618)
• If the default path is the story of the industrial world, then the pathless path is the natural story for a digital‐native world in which nothing can stop us from finding others who share our desires, ideas, and questions. (Location 1643)
• 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 1739)
• 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 1759)
• This is what Whyte means when he writes about the conversational nature of reality. It’s an acknowledgment that there are deeper forces at play in the world and we are a tiny little part of all that magic. It’s about existing within that magic and still daring to ask questions about what matters or where you fit in. Much of my previous life had been scripted into a routine and I spent almost all my time knowing where I was supposed to be. This short‐circuited my curiosity for years and kept me from seeing that there was a “conversation” with the world to be had at all. (Location 1854)
• When you step off the default path, you will be thrust towards the frontier. Almost immediately, clues about your conversation will emerge from what captures your attention and questions will appear that gives you a better understanding of what you’re really after. This will be a confusing time. You may feel the urge to tell everyone about your new insights, questions, and curiosities, but this can be a mistake. Your ideas may make others uncomfortable and any doubt, skepticism, or criticism they express could convince you to run away from the frontier. (Location 1858)
• 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 1866)
• Instead of optimizing for a future “exit,” or a sale of the company, he built a company he wanted to keep working at and all his decisions continue to be based on this goal. As his platform grew, corporations started asking the company to do customized installations for them. John decided he didn’t want to deal with these high‐maintenance customers and turned them down. Despite this obvious opportunity, 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 1891)
• 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. (Location 1899)
• It’s a shift from the mindset that work sucks towards the idea that you can design a life around liking work. (Location 1904)
• Finding work you want to keep doing, says author Stephen Cope, is “the great work of your life.” Cope’s biggest fear is that he might “die without having lived fully.”134 This impulse drove his curiosity as he sought out wisdom in books, reading upwards of three hours a day. Eventually, he wrote The Great Work of Your Life to explore the unique qualities of people who search for the things that bring them alive. His exploration was inspired by a passage he read in the Gospel of Thomas: 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.135 (Location 1911)
• the common trait they shared was seriously attempting to bring forth what was inside of them. This didn’t come easy to any of them and they all faced challenges, rejection, and criticism. Yet at every key point in their lives, they either kept looking for what brought them alive or protected their time so that they could work on what mattered. In the words of Thoreau, the game they played and that we should play is to “be resolutely and faithfully what you are.”136 (Location 1919)
• More important is the realization that finding something worth doing indefinitely is more powerful and exciting than any type of security, comfort, stability, or respect a job might offer. Fighting for the opportunity to do this work is what matters, whether or not you make money from it in the short term. (Location 1939)
• Usefulness, whatever form it may take, is the price we should pay for the air we breathe and the food we eat and the privilege of being alive. And it is its own reward, as well, for it is the beginning of happiness, just as self-pity and withdrawal from the battle are the beginning of misery.–Eleanor Roosevelt (Location 1949)
• Author Sebastian Junger, in his book about soldiers who had returned from war, found a similar thing. Despite dealing with post‐traumatic stress disorder, many of the soldiers wanted to return to dangerous warzones. Why? Because at war, they felt part of something, deeply connected to the men and women they were serving with. Junger reflected, “humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.”140 Junger argues that “modern society has perfected the art of making people not feel necessary.” (Location 1974)
• The positive side of earning a living by creating and sharing online or building an online business is often obscured by the logic of the default path, in which the worthiest endeavor is a full‐time job. Consider two different people: a mid‐level financial analyst at Wells Fargo and someone building a yoga business through Instagram. What’s your honest reaction to both people? If you’re like I was before I started working on my own, you’d probably be slightly judgmental of the Instagram influencer. Now, I’ve softened my stance. I’ve realized the yoga influencer puts their entire reputation at risk and succeeds or fails based on their decisions. As this kind of work becomes more prevalent, our norms will shift and we will question why we are more skeptical of an entrepreneur than the employee at Wells Fargo, a place that has been cited more than 200 times in the last 20 years for fraud, mortgage abuse, and violating investor rights.145 (Location 2093)
• Let’s recall Ben Hunt’s argument that these conventional, full‐time paths are no longer industrially necessary, but simply industrially preferable. If we continue to anchor our imagination to default path stories about work, we will continue to ignore the possible paths for our lives. (Location 2101)
• Even if you do decide that sharing your real work with the world is worthwhile, it’s nearly impossible to overcome the sense that you may embarrass yourself. Here it’s helpful to remember the “spirit of the fool” and also consider that many people around the world might be waiting for what you have to share. (Location 2103)
• Once people enter this new, creative mode, they realize that they’ve been holding back a part of themselves for most of their lives. Deep inside, we all have a desire to engage with the world in creative ways and don’t worry, I’m here to cheer you on. (Location 2126)
• Her reflections on the connection between critical thinking and hope in an interview with Krista Tippett on the On Being podcast helped me transform how I wanted to engage with the world. She argued, “critical thinking without hope is cynicism. But hope without critical thinking is naïveté.”147 (Location 2131)
• This desire for intellectual exploration with others has been a big theme on my journey. But not until I added hope to my critical thinking and embraced a more expansive view of the world did I attract the kind of people I wanted to welcome into my conversation. In my first couple of months in Taiwan, I read a book on writing by William Zinsser. He urged me to “believe in your own identity and your own opinions. Writing is an act of ego, and you might as well admit it. Use its energy to keep yourself going.”148 (Location 2137)
• In that single moment, I stopped hedging my bets. I would no longer fear what people might think, but I would also leave my cynical edge behind. After reading Zinsser, I put my heart into my writing and made my case. This was the way out of cynicism. I became more optimistic not because I started to write better or was right, but because I stopped hiding. I led with my curiosity, vulnerability, and passion and it immediately attracted the kind of people I wanted to meet. (Location 2142)
• In the early 1900s, professor and writer Bertrand Russell noted that “any person who visits the Universities of the Western world is liable to be struck by the fact that the intelligent young of the present day are cynical to a far greater extent than was the case formerly.”149 He argued that developing a cynical stance was necessary in a world in which much of what authorities and leaders claim directly contrasts with what is true. The cure for such cynicism, he said, would “only come when intellectuals can find a career that embodies their creative impulses.”150 (Location 2145)
• When I quit the New York Times to be a full-time mother, the voices of the world said that I was nuts. When I quit it again to be a full-time novelist, they said I was nuts again. 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)
• Instead of embarking on an endless search, I’ve taken a different approach: working 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. (Location 2172)
• One useful mental model for thinking about this is the principle of inversion, popularized by German mathematician Carl Jacobi. He told his students to “invert, always invert,” encouraging them to approach difficult problems by inverting the equation to gain a new perspective.151 We can also apply this principle to our lives. For example, 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 2175)
• I was inadvertently embracing a principle that professor Nassim Taleb calls “antifragility.” Antifragility is a well‐documented natural phenomenon in which things gain strength through disorder. For example, cities are antifragile. While individual businesses in a city may fail in an individual year, the city thrives over the long‐term, fueled by new residents, buildings, and businesses. (Location 2200)
• 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.”152 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. This is why I’ve spent so much time focusing on creating the conditions for success and lowering my risk of failure, rather than aiming at success itself. (Location 2207)
• In the paycheck world, there used to be a saying: dress for the job you want, not the job you have. The analogous idea in the free agent world is: learn to exercise the freedoms you might acquire, not just the freedoms you have.–Venkatesh Rao (Location 2217)
• Why would so many people trade some of their newfound freedom to join these authoritarian movements? Fromm argued that the reason lied behind two different types of freedom. First was negative freedom or “freedom from” outside control. Second was positive freedom or the “freedom to” engage with the world in a way that is true to yourself.” Fromm’s positive version of freedom was much more than the freedom to act. He described it as “the full realization of the individual’s potential, together with his ability to live actively and spontaneously.” 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 2231)
• Fromm, who was writing at the beginning of World War II, thought this a terrible mistake, even at the time: “because we have freed ourselves of the older overt forms of authority, we do not see that we have become the prey of a new kind of authority.”155 Abdicating our responsibility to live our own lives can have dire consequences. (Location 2240)
• The problem with conformity, Fromm argued, is that it leads to an existence that is too rigid, routine, and predictable. This undermines the space for spontaneity and active engagement that might help one discover what matters at a deeper level. (Location 2248)
• 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 2251)
• Ultimately, figuring out what to do with freedom once we have it is one of the biggest challenges of the pathless path. Writer Simon Sarris argues that we can only do this by increasing our capacity for agency, or our ability to take deliberate action in the world. He argues, “the secret of the world is that it is a very malleable place, we must be sure that people learn this, and never forget the order: Learning is naturally the consequence of doing.”158 In other words, only by taking action do we learn and only by learning do we discover what we want. Without this, we will struggle to take advantage of the freedom that the pathless path offers. We are ultimately the ones that determine our fate, and without expressing agency, we struggle to be free. (Location 2270)
• The default path has given us the freedom to earn money and spend it as we please, work in different fields, and have some control over our lives, but keeps many 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 2278)
• The pathless path is the deliberate pursuit of a positive version of freedom. Revisiting Fromm’s definition, “the full realization of the individual’s potential, together with his ability to live actively and spontaneously,” we see that developing our own sense of agency is vital.159 Thus, figuring out what to do with your time is a real concern. For this, I’ve found no better advice than the following from Dolly Parton: “Find out who you are and do it on purpose.”160 (Location 2280)
• In the 1970s, academic turned farmer Wendell Berry wrote about how economic success includes the hidden cost of depriving people “of any independent access to the staples of life: clothing, shelter, food, even water.”164 (Location 2332)
• I realized that this skill is worth practicing when I read a book called Sacred Economics by Charles Eisenstein. In it, he introduces the idea of a gift economy which he argues has been with humans for ages. He compares it to our default economic mindset: 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.165 (Location 2337)
• Seth Godin reminds us that the internet has “lowered the marginal cost of generosity” and I’m not sure most people realize the potential of this development. In the near future, people will have public digital wallets, and transmitting cash to someone we know or just met will be an ordinary event. This is why thinking about generosity as a skill and looking for opportunities to practice is important. (Location 2396)
• Eisenstein also realized the significance of relationships within the gift economy: One thing that gifts do is that they create ties among people—which is different from a financial transaction. If I buy something from you, I give you the money and you give me the thing, and we have no more relationship after that. I don’t owe you anything, you don’t owe me anything. The transaction is finished. But if you give me something, that’s different because now I kind of feel like I owe you one. It could be a feeling of obligation, or you could say it’s a feeling of gratitude. (Location 2404)
• The benefits of embracing the spirit of a gift economy are invisible to the people who ask me how I plan to monetize, scale, and grow my business. I’m not in the business of being a business. I’m embracing the work of building a life and all of the connections that will make that meaningful. (Location 2410)
• Beyond appreciating the work you want to do, embracing the spirit of a gift economy is a way to transcend our modern default assumptions about our value in the world to allow wonder, creativity, and connection to emerge and plant seeds inside us and the people around us. Through experiments over the past five years, I’ve realized that not only is generosity a skill worth practicing, but it has compounding benefits over time. (Location 2417)
• 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. When I see an opportunity to make money, scale something, charge more money, or move faster, this phrase reminds me to explore all possibilities first, including doing nothing. (Location 2430)
• This is one thing I think people get wrong about keeping options open. On the default path, optionality can be a trap. This is because you are trapped within your own career narrative. On the pathless path, however, optionality can pay consistent dividends because you are not holding out for another job but leaving space for a little more life. (Location 2450)
• Why am I doing all this? Why does it matter so much? I have bold aspirations. They may not be legible, measurable, or understandable to you, but they give my life a direction and a purpose. (Location 2453)
• “Dying,” Morrie suddenly said, “is only one thing to be sad over, Mitch. Living unhappily is something else. So many of the people who come to visit me are unhappy.” Why? “Well, for one thing, the culture we have does not make people feel good about themselves. We’re teaching the wrong things. And you have to be strong enough to say if the culture doesn’t work, don’t buy it. Create your own.”173 (Location 2481)
• This is what the pathless path is all about. It’s having the courage to walk away from an identity that seems to make sense in the context of the default path in order to aspire towards things you don’t understand. It’s to experiment in new ways, to remix your own path, to develop your own personal definition of freedom, and to dare to have faith that it will be okay, no matter how much skepticism, insecurity, or fear you face. (Location 2486)
• Unfortunately, embracing the pathless path means accepting that you might not know what you are doing and you might look like a fool. This is exactly how I felt in those first few months. But luckily many people have gone before me. I was guided by people like Morrie and Mitch Albom, and others, like Rebecca Solnit, who showed me that getting lost was simply the understanding that “the world has become larger than your knowledge of it.”177 (Location 2522)
• To help you on your journey, I’ve put together a list of ten things. This is both a summary of many of the lessons from this book as well as a challenge for you as you embrace the spirit of the pathless path. (Location 2553)
• 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. I tried to be a “good egg” but ultimately, found myself unhappy with the direction my life was headed. I stumbled into a pathless path and slowly realized that a rigid version of the default path that existed in my mind was only one option of many. (Location 2555)
• Second, reflect. When I started reflecting on my true self, I was able to start building a life around the things I valued. Most of us run on autopilot through life but we can break out of this mode by considering even the simplest reflection exercises. For me creating a daily reminder of four priorities that mattered to me and revisiting the leadership principles I aspired to in grad school helped me see that the gap between what I claimed to care about and how I was living was larger than I wanted. Through reflection, I was able to see that there was a larger “conversation” I was meant to have with the world. (Location 2558)
• 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 friends, asking them, “when have you seen me at my best self?” Their responses may surprise you and, perhaps, delight you. We all have stories about who we think we are and why we must be that way but often, others have a better perspective on what makes us stand out. (Location 2562)
• 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 minimum effective dose is at least a month away from work. While this may seem impossible or terrifying, this intervention has a near-universal approval rating and can have a profound effect on your confidence about the future. (Location 2566)
• 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, and how they think about navigating their life. Most people are much more enthusiastic about sharing what they’ve learned in their lives than we expect. To embrace the pathless path, you need friends and all you need at the start is one person. 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 the most valuable things you can do in life. (Location 2571)
• 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 permission. But you know this is not true anymore. Find a way to create. Host a dinner party, organize a volunteer event, write a blog post, start journaling in the morning, paint a picture, or host a cooking class for your friends. It doesn’t matter what you do, but the sooner you figure out a way to create and share with the world, the faster you’ll be able to move closer to finding the activities you want to continue doing throughout your life. (Location 2576)
• 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 to decouple your belief that security and money are perfectly linked. You don’t need to embrace the gift economy completely. Instead, you just need to pay attention and start making offers to share or give when the opportunity emerges. If you don’t have an idea, I’ll give you an easy way out: you can gift this book to someone that might enjoy it. Ultimately giving is a superpower on the pathless path and will enable you to transcend feelings of separateness and connect more deeply to the people around you. (Location 2581)
• 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 possible. Remember, the goal is not to get rich but always to figure out what to do next. (Location 2586)
• 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 to feel useful and to do things that challenged me to grow. This is why I believe that the “real work of your life” is searching for the things you want to commit to and that make your life meaningful. Once you find them, you can dedicate your time to creating the environment to make those things happen. (Location 2590)
• 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 if it required many attempts. He told Hume that if he tried eight different paths and failed, that he must keep searching: “you must find a ninth path.”178 Embracing the pathless path can be a slow and frustrating journey, one that happens at a different speed for everyone. 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 like it was a path I was meant to be on. Don’t rush things. Remember: nothing good gets away, as long as you create the space to let it emerge. (Location 2594)