Second, reflect. When I started reflecting on my true self, I was able to start building a life around the things I valued. Most of us run on autopilot through life but we can break out of this mode by considering even the simplest reflection exercises. For me creating a daily reminder of four priorities that mattered to me and revisiting the

First, question the default. For many years, I stuck with a story about how I thought my life should go. I assumed there was only one option for structuring my life, around full-time work. I tried to be a “good egg” but ultimately, found myself unhappy with the direction my life was headed. I stumbled into a pathless path and slowly realized that a

“The Tyranny of Convenience,” where he argues that convenience, “with its promise of smooth, effortless efficiency…threatens to erase the sort of struggles and challenges that help give meaning to life.”166

Professor and author Yuval Harari argued that “in order to keep up with the world of 2050, you will need not merely to invent new ideas and products, but above all to reinvent yourself again and again.”162

Nonetheless, I’ve come to see reinvention as one of the most valuable meta‑skills worth developing, and on the other side of these experiments, I am often much more relaxed and confident than before.

Ultimately, figuring out what to do with freedom once we have it is one of the biggest challenges of the pathless path. Writer Simon Sarris argues that we can only do this by increasing our capacity for agency, or our ability to take deliberate action in the world. He argues, “the secret of the world is that it is a very malleable place, we must be

I submit that this is what the real, no‑bullshit value of your liberal arts education is supposed to be about: how to keep from going through your comfortable, prosperous, respectable adult life dead, unconscious, a slave to your head and to your natural default setting of being uniquely, completely, imperially alone day in and day out.156

Over the last 100 years, the number of ways you can engage with life has exploded beyond imagination. Now, not only political leaders offer narratives for interacting with the world, but also employers, companies, media outlets, and other institutions. Everyone gives you roadmaps for living life and becoming free. You just have to buy their

Fromm argued that the reason lied behind two different types of freedom. First was negative freedom or “freedom from” outside control. Second was positive freedom or the “freedom to” engage with the world in a way that is true to yourself. Fromm’s positive version of freedom was much more than the freedom to act. He described it as “the full