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

Seth Godin puts it bluntly: “The world just gave you control over the means of production. Not to master them is a sin.”

When I was getting paid on a steady basis, the relationship between making money and my motivation was hard to understand. Without a paycheck, the combination of insecurity, fear, and my desire to prove myself made it much clearer. This ignited a period of frenzied activity, one which I’ve noticed is a common stage for people that leave their jobs

One challenge to embracing possibility is knowing when to override what psychology professors Gilovich and Davidai call our “‘ought to’ self.” This is the voice that helps us follow through on commitments but can also keep us from making changes in our lives. This is the voice that might convince you that leaving a job is an abdication of responsib

This means that for many people, expectations of life are centered around a small number of positive events that occur while we are young. Much of the rest of our lives remains unscripted and when people face inevitable setbacks, they are left without instructions on how to think or feel.

The biggest challenge to creating your virtuous cycle and one of the most dangerous failure modes of the pathless path is cynicism. Many people who leave the default path do so because they’ve become cynical and are driven by a desire to escape. But escaping is only the first step of leaving a certain path behind. In order to create a sustainable j

Despite thinking I wanted fun and joy at work for most of my career, when I reflect on the most meaningful moments of my career, they involve overcoming obstacles, or getting through setbacks to complete something I didn’t think I could.

“If work dominated your every moment, would life be worth living?”

In his book, On Liberty, published in 1859, John Stuart Mill was giving similar advice, arguing that societies need people to embrace their individuality and perform “experiments in living.” He argued that such experiments are vital to the pursuit of knowledge and that cultures only learn and evolve when original approaches to living are discovered

Do I still worry about money? Yes. But now I’m hyper‑aware of how my financial insecurities might distract me from efforts that will help me stay energized and motivated on this path. Instead of playing to not lose, I’m playing to win.