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

by Paul Millerd

The modern world offers an abundance of paths. In one sense this is great. It’s the result of an industrial system and resulting prosperity that has created opportunities for people around the world. However, the proliferation of paths presents a challenge. 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.

This is 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.

in the United States, one of the strongest “wage‑based societies” in the world, only about 40% of adult Americans, or 106 million people, have jobs where they work more than 35 hours per week.38

Many people realize they are on the wrong path after achieving impressive milestones.

shift your mindset from what you lack to what you have to offer, from ambition to aspiration, and from hoping that joy will result from a specific outcome to experiencing it as a byproduct of your journey.

The problem is that our culture has engaged in a Faustian bargain, in which we trade our genius and artistry for apparent stability. – Seth Godin

More important is the realization that finding something worth doing indefinitely is more powerful and exciting than any type of security, comfort, stability, or respect a job might offer. Fighting for the opportunity to do this work is what matters, whether or not you make money from it in the short term.

On the default path, you have to get the job before you can do the work. On the pathless path, you simply do the work first and then decide if you want to continue.

Tyler Cowen has argued that one of “the most valuable things you can do with your time and with your life” is to believe in people.144 Being a recipient of this encouragement has inspired me to create a rule for myself: any time I consume something from an individual that inspires me, I have to send them a note to let them know. Creating and sharing in public takes an incredible amount of courage and I remember how awkward and scared I was at the beginning of my journey. It’s easy to tell people what they got wrong but much harder to say “I love what you are doing. I hope you keep going and let me know if I can help.”

“critical thinking without hope is cynicism. But hope without critical thinking is naïveté.”

One useful mental model for thinking about this is the principle of inversion, popularized by German mathematician Carl Jacobi. He told his students to “invert, always invert,” encouraging them to approach difficult problems by inverting the equation to gain a new perspective.151 We can also apply this principle to our lives. For example, instead of asking what makes up an amazing life, we first define the worst‑case scenario and then work backward. What does a miserable life entail? What actions would make achieving such a life more likely? Then figure out how you can avoid these things from becoming true.

The problem with conformity, Fromm argued, is that it leads to an existence that is too rigid, routine, and predictable.

The default path has given us the freedom to earn money and spend it as we please, work in different fields, and have some control over our lives, but keeps many trapped in a pseudo‑freedom where one is free from absolute oppression but not free enough to act with a high degree of agency.

When we think about the future, we tend to underestimate how much things will change, especially for ourselves. Researchers call this the “end of history illusion.” Across all age groups, people indicate that they have experienced profound change in the past but when they forecast their future, they don’t see the trend continuing.

Professor Tim Wu made this point in a widely read essay titled “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

What is the low range of a price you would be willing to offer for an online course? What is the high range of a price you would be willing to offer for an online course? What is a gift that “feels right” for this course that you are able to give wholeheartedly?

Coming alive over getting ahead.

If the culture doesn’t work, don’t buy it. Create your own.

To create your own culture on the pathless path you must identify the assumptions you make in your approach to life. Here are some of my assumptions, many of which have been sprinkled throughout this book: Many people are capable of more than they believe. Creativity is a real path to optimism, meaning, and connection. We don’t need permission to engage with the world and people around us. We are all creative, and it takes some people longer to figure that out. Leisure, or active contemplation, is one of the most important things in life, There are many ways to make money, and when an obvious path emerges, there is often a more interesting path not showing itself. Finding the work that matters to us is the real work of our lives.