Note: While reading a book whenever I come across something interesting, I highlight it on my Kindle. Later I turn those highlights into a blogpost. It is not a complete summary of the book. These are my notes which I intend to go back to later. Let’s start!

  • As the world continues to change and technology reshapes our lives, the stories we use to navigate life become outdated and come up short. People are starting to feel the disconnect between what we’ve been told about how the world works and what they experience. You work hard, but get laid off anyway. You have the perfect life on paper, but no time to enjoy it. You retire with millions in the bank, but no idea what to do with your time. The pathless path has been my way to release myself from the achievement narrative that I had been unconsciously following. I was able to shift away from a life built on getting ahead and towards one focused on coming alive. I was able to grapple with the hard questions of life, the ones we try so hard to ignore. And I was able to keep moving when I realized that the hardest questions often don’t have answers.

  • Ranjit and I were both pulled by the force of the impressive stories associated with prestigious jobs like strategy consulting and law. These paths are too good to be true for driven young people who want to turn their success in school into something tangible for others to see. Zen philosopher Alan Watts argued that “the desire for security and the feeling of insecurity are the same thing,” and that “we look for this security by fortifying and enclosing ourselves in innumerable ways. We want the protection of being ‘exclusive’ and ‘special.’” This was exactly what I was looking for. 

  • What I really wanted was to be part of the “inner ring,” which C.S. Lewis famously detailed in a lecture given at King’s College in 1944. He argued, “…in all men’s lives at certain periods…one of the most dominant elements is the desire to be inside the local Ring and the terror of being left outside.”

  • Before the fall semester of senior year, I had built a spreadsheet of consulting companies and other jobs perceived as prestigious. This was the inner ring I cared about. Beyond consulting companies, it included investment banks, technology startups, and hedge funds. I wasn’t picky about the type of work I’d be doing, I just wanted it to be seen as impressive. I spent most of that semester in a frenzy, searching for companies I had missed, networking, sending cold e-mails, and trying to land interviews. Unfortunately, most of my efforts were met with near-instant rejection. My credentials were good enough but most of the companies had met their hiring targets with students from better schools.

  • After graduation, I made the two-day drive to Ohio with my cousin Brian. I remember two things about the drive: Hey There, Delilah coming on the radio every forty minutes and being filled with a sense of unease. For the first time, I would be living outside of a 15-mile bubble in Connecticut. Moving to a new city and working for a great company like GE was exciting, but deep down I felt like I wasn’t where I wanted to be. I tried to pretend I was happy to be starting the job, but I wanted more. 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. My colleagues had been coming to the same desks for decades and were more interested in their retirement portfolios than working and told me that if not for the benefits, they probably wouldn’t show up.

  • I adopted this attitude and embraced a version of a career which philosopher Andrew Taggart, who writes about our modern relationship to work, describes as “a first-person work-centric story of progress about an individual’s life course.” From this perspective, my career was not a series of jobs, but a high-stakes proposition, one where falling behind felt like failure. My colleagues and I dealt with this pressure by constantly talking about potential career paths and “exit options.” This was helpful for someone new to this world like me. I could figure out how to stay in the inner ring by following the wisdom of my peers.

  • A year went by and I decided my next step was going to a top business school. This idea did not emerge out of thin air. Talks of applications, essays, and school rankings filled the daily lunchroom conversations. These people were my friends and when they were accepted into elite business schools like Harvard and Stanford, it seemed obvious that I should do the same thing. This is the trap of prestigious career paths. Instead of thinking about what you want to do with your life, you default to the options most admired by your peers. In describing the power of the inner ring, C.S. Lewis warns that, ”unless you take measures to prevent it, this desire is going to be one of the chief motives of your life, from the first day on which you enter your profession until the day when you are too old to care.” He believed “any other kind of life, if you lead it, will be the result of conscious and continuous effort.”  In this world, the natural thing was to leave McKinsey, despite loving the work, because that was what everyone did. Near the end of my second year, I was accepted into a dual-degree program at the Massachusetts Institute of Technology. If you had shown me Lewis’ quote and tried to convince me there was any “other kind of life” I would not have believed it. The path I was on was too good to be true and I was more than happy to be on it.

  • The philosopher Andrew Taggart believes that crisis moments lead to “existential openings” that force us to grapple with the deepest questions about life. 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.

  • With a new doctor in Boston, I found better treatments that worked and after more than a year of struggling, I started to improve. I returned to work part-time and eventually full-time, but I was not the same person. While I was sick, I had contemplated the question, “what would people think if I couldn’t work again?” and had been surprised by my answer. I would be okay. So much of my identity had been connected with being a high achiever. Straight A’s. Dean’s List. McKinsey. MIT. When I was sick, I would have traded every last credential for a single day of feeling okay. As I started to feel better, a different kind of energy showed up in my life. Professors Richard Tedeschi and Lawrence Calhoun have suggested that many people who face crises often experience “post-traumatic growth” and that this manifests as an “appreciation for life in general, more meaningful interpersonal relationships, an increased sense of personal strength, changed priorities, and a richer existential and spiritual life.

  • In 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.” With the introduction of a “calling,” Luther and then Calvin both wanted to undermine the authority of the Catholic Church to govern an individual’s relationship with God. Luther took issue with the Church’s system of “indulgences,” in which people paid the Church to absolve them of their sins. He thought individuals should be able to have their own relationship with God. Calvin paired Luther’s increase in individual freedom with the idea that everyone is predestined to serve God through a specific calling. Working hard in the area of one’s calling determines the status of a person’s relationship with God. In the 1940s, philosopher Erich Fromm summarized this transformation, saying, “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.” Following the Reformation, then, work as an end in itself was no longer a crazy idea. People traded one master, the Catholic Church, for another, their vocation. But along with greater freedom and self-determination came the anxiety and insecurity of never really knowing if you were working hard enough or doing the right thing. The Church’s expectations had always provided a way to measure “goodness,” and for many, these benchmarks no longer applied. Over the last 500 years, this freedom has taken us in many different directions, yet remnants of the Catholic and Protestant conceptions of work are still with us. When entrepreneur Gary Vaynerchuk tells us in his book Crush It to “wake up before everybody else and work into the night. Hustle,” he accepts both the duty of work and absolute commitment to work as integral to life. Oprah Winfrey channels a modern spin on Calvin’s calling, arguing that “each of us has a personal calling.” To her, the “best way to succeed is to discover what you love and then find a way to offer it to others in the form of service, working hard, and also allowing the energy of the universe to lead you.”

  • These Catholic and Protestant perspectives on work are deeply embedded in the modern default path view of work that spans the globe but has become detached from the time periods and traditions from which they emerged. Religious scholars point out that the Protestant “work ethic” is more than a blind obsession with work. It is paired with thrift, self-discipline, and humility. Yet as fewer people look to religion for wisdom on how to navigate life, they are only left with the watered-down version of these views.

  • It wasn’t until my early 30s that I started to suspect something was amiss. Like many of the people I knew, I was single, renting, and living and working in a city away from my hometown. Those who were starting families were overwhelmed with the costs of daycare, healthcare, and housing. We entered adulthood thinking we could copy-and-paste what our parents had done, but it was more complicated than that. Factors that support meaningful lives, like economic growth across all sectors, a young population, two-parent households, generous pensions, and company loyalty were anomalies of the past. Starting my career, I didn’t understand any of this. Plus, I was too busy getting sucked into a new idea. That you didn’t simply work to live, but that it should be one of the most important things in your life.

  • Despite thinking I wanted fun and joy at work for most of my career, when I reflect on the most meaningful moments of my career, they involve overcoming obstacles, or getting through setbacks to complete something I didn’t think I could.

  • When he got raises or promotions the discomfort would subside but never disappear. Slowly, he became more curious about that feeling and realized that despite his external success, he had become a “passive participant” in his life. Eventually, this convinced him to embark on his own pathless path. When I returned to work after regaining my health, I had discomfort that could only be described the way Khe put it, as a pebble in my shoe. It wasn’t enough of a feeling to make me do anything dramatic, but it threw me off just enough that I was forced to pay attention to my life in a different way. As I started to pay attention, I slowly came to realize the reality that I had been living in was an invisible bubble, one of my own creation. I started to push the edges of that reality and wasn’t sure what would happen.

  • I created a daily calendar entry of priorities for my life. First on my list was health. After recovering from my health challenges, I would do anything to stay healthy. Next, my head told me to list “career,” but my heart told me to list it last. This simple decision was my first conscious commitment to exploring the possibility of a life not centered around work. 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. 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?”

  • Daniel Vassallo describes experiencing a similar shift ten years into his career at Amazon: “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.” He came to the conclusion that “only intrinsic motivation lasts” and decided to leave a comfortable six-figure salary behind and create a life designed around flexible work, his interests, and his family.

  • 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. It was easier to aim toward another raise or promotion than daring to ask myself deeper questions. A passage from William Reilly’s book How To Avid 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. My path was suffocating part of me that I wanted to let breathe. I had to do something.

  • I sat in my hotel room and didn’t know what to think. I could stop what I had set in motion, but I didn’t. I felt excited but confused. Did I just quit? I walked down to the pool to start the wedding weekend, saw a friend, and said, “I think I just quit my job.” So much of life is like this. We are surprised at the moment something happens, but looking back, we realize that everything makes sense. Losing my grandfather, getting rejected from jobs repeatedly, never finding the right fit, facing health challenges and hard questions were all events that sent me in an inevitable direction that was only obvious upon reflection. When I quit, it was the only thing left to do. It took me 10 seconds at the bottom of an email.

  • No single day stands out. I stuck to my daily routine, arriving each morning at the 7 train subway platform. I boarded the train for the single-stop journey from Queens to Manhattan. Then I slid my body into the masses of people and became part of a massive blob of workers making our way into the mecca of work. Each day I searched for signs of life. I would force a smile and look around to see if anyone noticed. No one ever did. So I gave up and adopted the neutral uninterested smirk that everyone seemed to understand was the proper way to be. 

  • As my money anxieties receded, I realized I wanted to go deeper. Not with freelance work, but in my life. In those first six months, I experienced a remarkable sense of freedom and ownership over my life. Most days I decided when, where, and how I worked. It differed radically from how I had spent my days on my previous path and this made me curious enough to consider a question that would push me deeper into an exploration of my relationship to work.

  • Yet when I became self-employed, I was surprised at how strongly I had internalized a worker identity. As I struggled to find my first project, I felt guilty when I wasn’t working during typical work hours Monday through Friday. When I started working remotely on my first project, I had 100% control over when and how I did the work, but quickly fell into a routine of going to a coworking office five days a week. 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.  As I started to experiment with how I spent my time, Taggart’s question remained in my head. I was fascinated by his claim that 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.

  • For most people, life is not based on all-or-nothing leaps of faith. That’s a lie we tell ourselves so that we can remain comfortable in our current state. We simplify life transitions down to single moments because the real stories are more complex, harder to tell and attract less attention. The headline, “Quits To Live on a Sailboat” seems more impressive and is easier to talk about than “Couple Slowly and Purposefully Tests Out a Life Transition while Aggressively Saving Money over Five Years.“ As a result, we hear fewer of the real stories, most of which include some kind of prototyping. 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.

  • 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. So people avoid change and develop coping strategies. They learn to sidestep the manipulative manager, or like me, change jobs every couple of years, plan vacations, stay busy, and get drunk during the weekend. Play this game long enough without becoming too burned out and you might end up getting promoted. We can explain this strategy with a simple equation:Uncertain Discomfort < Certain Discomfort + Coping MechanismIn other words, given sufficient coping strategies, people will be willing to tolerate consistent levels of misery for long stretches of time. 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. Wonder is the state of being open to the world, its beauty, and potential possibilities. With wonder, the need to cope becomes less important and the discomfort on the current path becomes more noticeable. The equation becomes:Uncertain Discomfort + Wonder > Certain Discomfort

  • 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. They get curious about who they might become if they embrace discomfort and are filled with a sense of urgency that says, “if I don’t do this now, I might regret it.” 

  • Making life changes requires overcoming the discomfort of not knowing what will happen. Facing uncertainty, we make long mental lists of things that might go wrong and use these as the reasons why we must stay on our current path. Learning to have a healthy distrust of this impulse and knowing that even if things go wrong, we might discover things worth finding can help us open ourselves up to the potential for wonderful things to happen.

  • Although people considering the option of leaving the default path can list hundreds of things that might go wrong, they struggle to talk about the fears behind those risks. 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?”

  • When you’ve spent your entire life studying for the test and compiling long lists of achievements it can be hard to believe that true success is that simple. In the consulting industry, bad tests were prevalent. While the quality of your work was important, other tests like getting senior partners to like me, taking any work given to me, dressing the right way, and learning to speak in a certain way were much more important in getting promoted, getting a raise, and continuing on an impressive career trajectory. I don’t think I realized how much I hated this until I became self-employed and immediately stopped spending any time hacking tests. With freelancing, I was competing on the quality of my ideas and my ability to do good work for clients. A lot of former consultants who become freelancers are surprised at how much less time it takes to do the same work. This is not because it’s any easier. In fact, it’s a lot harder without the support of an entire firm’s resources. It’s just that there are no longer hundreds of different people you need to impress. 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. Despite this, it’s interesting to see how people map their own understanding of how they think the world works onto my current path. Many people say things like, “you can do this because you worked at McKinsey and went to MIT.” They assume that my credentials are what matter most. I wish this were the case! While having impressive credentials can open doors, it hasn’t translated into a high income, especially with some of the more creative things I’ve done like writing or online courses.

  • On the pathless path, knowing you have enough is what gives you the freedom to say “no” to clear financial opportunities and say “yes” to something that might bring you alive and might even pay off much more over the long term. When I launched a podcast, people assumed it was a massive project and that I wanted to compete with Gimlet and NPR. They didn’t know that I considered it an experiment and wasn’t aiming toward monetary success or fame. From this perspective, it made sense to create a podcast cover in 20 minutes in PowerPoint, spend less than an hour editing the audio, and publish without much of a following. There was nothing else to gain because I was operating from the feeling of enough. If we don’t define “enough,” we default to more, which makes it impossible to understand when to say no. 

  • On the pathless path, the pressure of conformity is not a major concern, but that does not mean an ideal life will emerge automatically. You need to take steps to create it, and in those months in Asia, I started to realize that I needed to graduate from my role as accountant. Minimizing spending is a useful step in lowering the pressure of making money, but it’s not a lifestyle. While it gave me the confidence to make drastic changes without sacrificing my happiness, it kept me in a mindset of scarcity instead of leaning into possibility. Do I still worry about money? Yes. But now I’m hyper-aware of how my financial insecurities might distract me from efforts that will help me stay energized and motivated on this path. Instead of playing to not lose, I’m playing to win. Behind our money fears are existential fears, like the fear of death or the fear of not being loved, respected, and admired. These fears are likely not solvable but we can learn to coexist with them. This is also why financial worries can be infinite and people can chase more and more their entire lives. The flip side of this is that if we can learn to coexist with our financial insecurities, we can turn them into a secondary concern. This opens you up to the real secret: the opportunities of the pathless path are infinite too.

  • I was first forced towards the edge of my reality the first week after quitting my job. I set out to wander around New York and ended up at a park called the Cloisters, at the literal frontier of New York, a city that I had failed to fully explore in the two and a half years that I had been there. I wandered through the park overlooking the Hudson. I felt lost, but not in a way that I could do anything about. If you had asked me where I was headed, I wouldn’t have had an answer. If you suggested I might move to Boston in a few months, I might have believed you. But if you said I’d end up in Asia, married, a little over two years later? I wouldn’t have even known what to do with that information. Being at the frontier of your current reality is disorienting. Deep down you might have a sense that you should keep going in a certain direction, but you never know why. 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. 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. My own conversation has evolved slowly. At first, it was a solo conversation with broad, ambiguous questions ignited by losing my grandfather and losing my identity during my health crisis. This morphed into a more complex conversation over time, one that involved realizations from my life as well as from other people I was meeting through my writing. These connections were vital to staying at the frontier and exploring.

  • John O’Nolan set a goal for himself to build a $1 million company by the time he turned 30. After several failed attempts, he decided to reevaluate. He realized that if he stuck to this goal, he might achieve it, but he might build a company he didn’t want to be part of. He shifted his approach towards building a business that he wanted to be “stuck with” and revisited an idea that he had sidelined: building a new blogging platform. His idea seemed silly. Everyone used dominant platforms like WordPress or Blogger. Who was he to try to compete in that space? Nevertheless, he decided to go for it and founded a new blogging platform named Ghost. To ensure that he was taking a long-term approach, John made decisions that differed radically from those that are made in a traditional startup. For example, he wouldn’t control the shares and he would not be able to sell the company. In an interview with Ali Abdaal, he said, “I don’t own Ghost. I am a trustee of Ghost, which means I can steer it as an owner would, but if I ever get sick of it, I can’t sell it. I don’t own any shares.” This is opposed to how almost everyone in the technology industry operates, but it makes sense if you’re planning on sticking with the company you’re building. 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. 

  • In my travels around the world, meeting a diverse range of people that have left the default path, nothing has been more consistent than the reality that most people want to engage with the world and to be useful. Despite many people thinking that their ideal life would be living out the rest of their life on a beach, when given the option of following that path, few people take it. 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.” Junger argues that “modern society has perfected the art of making people not feel necessary.” The need to feel useful is a powerful one. This is the hidden upside of the pathless path and a reason why finding work that aligns with what matters to you and makes you feel useful is so important. When you find the conversations you want to take part in and the work you want to keep doing, you start to feel necessary and the whole world opens up.