The Pathless Path: Imagining a New Story For Work and Life (The Pathless Path Collection Book 1)
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Many people are surprised to find out that in the United States, one of the strongest “wage‑based societies” in the world, only about 40% of adult Americans, or 106 million people, have jobs where they work more than 35 hours per week.38
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Seeing the job as a central element of a good life and employment rates as a metric of a successful society was not a common assumption until after World War II. In 1946, the United States formalized this by passing the Full Employment Act “to promote maximum employment.”39
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In 2016, economists Lawrence Katz and Alan Kreuger highlighted a group of 30 million people categorized by the U.S. government as “alternative” or “nontraditional” workers and showed that they were responsible for nearly all of U.S. job growth from 2005 to 2015, adding nearly 10 million jobs.43
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McKinsey compared these workers to “traditional” employees and found that they were as satisfied or more satisfied across fifteen different work characteristics, such as income, independence, hours, flexibility, creativity, and even recognition.44
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“Why the hell are so many grown adults spending their time on obviously pointless tasks?”
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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
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beyond the headlines of dramatic life changes are almost always longer, slower, and more interesting journeys.
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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? Once you ask these questions there is no going back. Not because of the contradictions in other people’s lives, but because it makes it difficult to live in contradiction in your own life.
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My final list included four items: health, relationships, fun & creativity, and career.
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“How do you design a life that doesn’t put work first?”
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The answer, my dear reader, is simple. You start underachieving at work.
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“creative work runs on uncertainty; it runs on not knowing what you’re doing.”46
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A few years into the path, however, the things I was incentivized to learn became specific to the organization, such as navigating political conflicts and adopting behaviors, dress, and attitudes that signaled I might be a future company leader.
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As I sat there, I didn’t know how to want it anymore.
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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.
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William Reilly’s book How To Avoid Work,
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Finally, I had become too serious about work. At some point, I had lost my sense of humor and was spending far too much time getting caught up in company politics.
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“How are you complicit in creating the conditions you say you don’t want?”
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Anyone who has worked in client or customer‑facing jobs knows that the work mostly focuses on reacting to ongoing mini‑crises.
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“I think I just quit my job.”
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While working, I always sensed that these feelings were there, but the daily inertia of a life centered around work kept them hidden. Now, without a plan and without anywhere to show up, I had to feel the full force of my emotions.
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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 so?
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I found my way out and as I finished writing the piece, I felt a sense of relief wash over my body. I was able to forgive myself for some of my failures in that job and with that, I was ready to move forward.
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This was the first of many experiences in which I pushed past the default setting of how I was supposed to be living.
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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.
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I told her I was excited about having space to experiment, explore ideas, and not have to work for someone else. She was confused and asked, “why not just find another job?”
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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.
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“If work dominated your every moment, would life be worth living?” the philosopher Andrew Taggart
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I felt guilty when I wasn’t working during typical work hours Monday through Friday.
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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.
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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.
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the German philosopher Josef Pieper, who first wrote about it in his book Leisure, The Basis of Culture. Writing in Germany after World War II, Pieper was shocked at how people were eager to throw themselves into work without pausing to reflect on what kind of world they wanted to build. To Pieper, this was evidence that German society had abandoned a connection to a traditional form of leisure.
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He noted that the ancient Greek translation for “work” was literally “not‑at‑leisure.”
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Now, this is flipped. We work to earn time off and see leisure as a break from work.
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Are you a worker? If you are not a worker, then who are you? Given who you are, what life is sufficient?
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When people asked how my work was going, I offered a hand‑wavey response, trying to hide my guilt of pursuing such a radical experiment.
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In my official, public story I was doing freelance consulting, but really I was taking my first sabbatical, learning how it felt to live life not oriented around work.
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Now it didn’t matter when I worked on my projects. They were energizing and rarely left me drained. For a long time, I had thought that if I wanted to be happier with my work, I just needed a better job. Now I saw that I just wanted a different relationship with work, one that, at least for now, didn’t come with a paycheck. A
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61 Similar to expectations around meaningful work, far too many people limit their imagination of work worth doing to things that either come with a paycheck, require qualifications, or have a socially accepted story of impact.
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This weird kind of life was only possible due to the internet, and I could not have imagined it even one month earlier.
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The one who wonders not only does not know, he is intimately sure that he does not know, and he understands himself as being in a position of not‑knowing.
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This kind of approach, focused not on being brave, but instead on eliminating risk, is common for people who take unconventional paths.
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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.
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Uncertain Discomfort < Certain Discomfort + Coping Mechanism
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In other words, given sufficient coping strategies, people will be willing to tolerate consistent levels of misery for long stretches of time.
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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:
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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.”
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One challenge to embracing possibility is knowing when to override what psychology professors Gilovich and Davidai call our “‘ought to’ self.”
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This impulse is helpful most of the time, but compounded over one’s life it stops us from moving towards what Gilovich and Davidai call our “ideal self.” When people reflect on their lives, these are the things that people regret most – not moving towards their ideal selves. The professors argue that people rarely regret the things they do in their lives. This is exactly because of the power of our “ought to” selves – even if we fail, we tend to take immediate action to fix those mistakes.67
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“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.”