The Pathless Path: Imagining a New Story For Work and Life (The Pathless Path Collection Book 1)

by Paul Millerd

Most mornings I came into the office and sat there struggling to start my day. I watched the people pass my desk and wondered if they felt the same stuckness as I did.

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.

With so many options it can be tempting to pick a path that offers certainty rather than doing the harder work of figuring out what we really want.

The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything. – David Foster Wallace

Daniel Vassallo describes experiencing a similar shift ten years into his career at Amazon: “Everything was going well and getting better. But despite all this, my motivation to go to work each morning was decreasing – almost in an inverse trend to my career and income growth.”

For most people, life is not based on all‑or‑nothing leaps of faith. That’s a lie we tell ourselves so that we can remain comfortable in our current state.

The headline, “Quits To Live on a Sailboat” seems more impressive and is easier to talk about than “Couple Slowly and Purposefully Tests Out a Life Transition while Aggressively Saving Money over Five Years.“

Gretchen Rubin decided to override her “ought to” self when she said, “I’ve come to a point where I’d rather fail as a writer than succeed as a lawyer, and I need to try and fail or try and succeed, but I need to do it.”68 Rubin attended Yale Law School, clerked for Sandra Day O’Connor on the Supreme Court, and was at the start of a high‑paying and promising law career. Yet, she understood that if she kept going and never took a chance on becoming a writer, she would regret it.

Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.”

Kevin Jurczyk, took a planned sabbatical, he shared with me, “I used to think ‘this job isn’t so bad, I make enough money to make it worth it.’ Then you get a breath of freedom and realize, no, it may have been worth it at one point, but not anymore.”82

shame is still associated with taking a different path.

Ryan Holiday wrote, “You know deep down that accomplishing things won’t make you happy, but I think I always fantasized that it would at least feel really good. I was so wrong. Hitting #1 for the first time as an author felt like…nothing. Being a ‘millionaire’…nothing. It’s a trick of evolution that drives us, and no one is immune from making this mistake.”

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.104

Walden Pond, “Not till we are lost, in other words, not till we have lost the world, do we begin to find ourselves, and realize where we are and the infinite extent of our relations.”123

Are you helping people? Are they happy? Are you happy? Are you profitable? Isn’t that enough? – Derek Sivers

Junger reflected, “humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.”140

Learning is naturally the consequence of doing.”158 In other words, only by taking action do we learn and only by learning do we discover what we want.

getting lost was simply the understanding that “the world has become larger than your knowledge of it.”177