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.” 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).

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.” 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.” 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.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.” It’s tempting to tell a simpler story. People want to hear about bold acts of courage, not years of feeling lost. On my way toward leaving my job, I never had a clear picture of my next step.” 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 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). an aspirational and alternative to the default path (a new story for thinking about finding a path in life; a call to adventure in a world that tells us to conform; a define-your-own-success adventure).

Who Is Really Happy” uses the discovery of a human skull on the roadside to probe into the question of immortality and how misery arises out of the existence of the ego. 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.” No Rest for the Living” uses a dialogue between a despondent seeker and his master to reveal the limits of philosophy and the crippling consequences of living for the sake of some future goal. 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).

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). 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). optionality can pay consistent dividends (because you are not holding out for another job but leaving space for a little more life). Simple questions from others like ‘what do you do?’ will expose your own uncertainty and can feel like a death blow to the soul.”

Opting out of work and opting in to other aspects of your life can create questions about who you used to be. It feels weird at first, but over time, you start to change what you value.” People become aware of their own suffering. Often we don’t notice our drift into a state of low‑grade anxiety until we step away from what causes it, as I noticed the first day after I quit my job and realized I was burned out.” worry is traded for wonder (people stop thinking about worst‑case scenarios and begin to imagine the benefits of following an uncertain path. 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.” ignoring the shiny objects and distractions (and stripping away the stories that are not our own to remember who we are).By my late 20s, I had oriented my entire life around work. I was always thinking about how I could get a better job or a higher salary.” 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.”