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

The more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we’re too poor to buy our freedom. – Rolf Potts

The pathless path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It’s a call to adventure in a world that tells us to conform. For me, it’s also a gentle reminder to laugh when things feel out of control and trusting that an uncertain future is not a problem to be solved.

“humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.”⁠

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

Here’s the truth you have to wrestle with: the reason that art (writing, engaging, leading, all of it) is valuable is precisely why I can’t tell you how to do it. If there were a map, there’d be no art, because art is the act of navigating without a map. Don’t you hate that? I love that there’s no map. – Seth Godin

Behind our money fears are existential fears, like the fear of death or the fear of not being loved, respected, and admired. These fears are likely not solvable but we can learn to coexist with them.

People are very aware of the absurdity of much of what you have to do to succeed in different companies and institutions, but still often gaslight themselves by starting off their own complaints with, “I know I should be grateful, but…”.

This is what Harvard professor Dr. Ben‑Shahar calls the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness.

Many people I talk to are convinced that the formula for living on their own terms is saving up enough money. I wish they knew what I know: the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is.