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

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the goal is to stay on the pathless path indefinitely (what author James Carse calls the “infinite game”; an infinite game for the purpose of continuing the play). 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.” optionality can pay consistent dividends (because you are not holding out for another job but leaving space for a little more life). makes commitments (to a type of work, ways of living, creative projects, or a “conversation” with the world; finding ideas and principles worth committing to and seeing where you end up). I was still searching for that elusive dream job and had not yet considered becoming self-employed.”

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.” My mother credits the health crisis I faced in my 20s for putting me on my current path. ‘It changed you,’ she says. While I don’t think it was the sole reason I left the default path, my illness did change my relationship to uncertainty.” A Systems Approach to Lifestyle Design: “Early Retirement Extreme” by Jacob Lund Fisker (Book Summary)+ 🔒 Premium Synthesis 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.” 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.”When I quit, my mindset shifted immediately and I looked at every monetary transaction with the intensity of a financial auditor.” Most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them.”

Best Be Still, Best Be Empty” discusses the difference between the path of the will, the via affirmitiva of Christianity, Judaism, and Islam, versus the path of the mystic, the via negativa of Buddha and Lao Tzu. 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.” While I don’t have perfect answers yet for the questions I keep asking, my conversation has somehow turned into a full life, one filled with people, ideas, curiosities, and work that will keep me engaged for many years to come.” 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.

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).

As I was growing up, work was such an obvious goal of life that I never paused for a moment to question it.” 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.” What I want to keep doing, such as mentoring young people, writing, teaching, sharing ideas, connecting people, and having meaningful conversations, is worth fighting for.” When I became self‑employed, I was surprised at how strongly I had internalized a worker identity.”The natural story for a digital‑native world in which nothing can stop us from finding others who share our desires, ideas, and questions. 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. You simply do the work first and then decide if you want to continue. In sum, the goal of being on this path is: Being able to get to a state of being where I can spend almost all my time helping, supporting, and inspiring others to do great things with their lives. On the pathless path, retirement is neither a destination nor a financial calculation, but a continuation of a life well-lived. This shifts attention from focusing on saving for the future to understanding how you want to live in the present.”