The Pathless Path: Imagining a New Story For Work and Life

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Giant corrupted spirits lurk in the woods. Use all your skill to hunt them down, but be careful not to become the hunted yourself. Engage in epic battles against the cursed beasts to restore light to the land. The bond with your eagle and the fate of the world hang in the balance. a series of decisions and accomplishments needed to be seen as a successful adult (these vary by country, but in the United States, we refer to this as the ‘ American Dream,’ which means a life centered around a good job, owning a home, and having a family). following a script (for most of my life, I had followed a script about how life should be, always trying to choreograph my future; I took classes with the sole intention of getting the best grade possible; I did not change radically as a person because nothing was at stake). I was still searching for that elusive dream job and had not yet considered becoming self-employed.” The pathless path has helped me see that quitting my job was never about escaping work or living an easier life, it was about using the gifts I received from my parents to benefit others.”

People aim for ‘ financial independence‘ only to realize when they achieve it that they’re only independent in the narrow sense of being able to pay for everything.”Behind my money fears was a longing to feel that my life mattered. I suspect this is the same for many, and money is one shortcut we use to ‘prove’ our worth. Yet in my experience, no amount of money ever seems to satisfy.” ignoring the pull of needing to be a “good egg” and learning what truly enables you to thrive (what this really means is developing an appreciation for discomfort).

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. 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.” The story of the industrial world. An industrial, “bigger is better” mindset assumes that everyone is competing in a mass market. Thinking we have to serve a mass audience is default path thinking. You have to get the job before you can do the work.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.’ 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. This is the ethos of the pathless path and if you don’t know or understand your own story, you will struggle.” biggest problem is the paradox of choice (there are too many interesting things worth doing and too many places to visit). I always took all of my vacation days. Didn’t work crazy hours. Made time for friends and family. Changed jobs when I stopped learning.”

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 (but 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). Years of resentment, frustration, and confusion demanded to be released. 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.”

a mantra to reassure myself I would be okay (after spending the first 32 years of my life always having a plan, this kind of blind trust in the universe was new, scary, and exciting).

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).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.” 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.” The work that I want to keep doing is writing, sharing stories, helping people, and doing other experiments online.” the deliberate pursuit of a positive version of freedom (figuring out what to do with freedom once we have it is one of the biggest challenges of the pathless path).