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

exploring. In my favorite essay, “Solitude and Leadership,” William Deresiewicz highlights the importance of searching for wisdom in real conversations with close friends:

Embracing the pathless path can be a slow and frustrating journey, one that happens at a different speed for everyone. It took me years to build up the courage to quit my job and then several more years to find a mix of work, people, and a way of orienting in the world that felt like it was a path I was meant to be on. Don’t rush things. Remember:

Money might help pay for therapy, time off, and healing retreats, but it won’t help you come to a place where you really trust and know that everything will be okay.

Wonder is the state of being open to the world, its beauty, and potential possibilities. With wonder, the need to cope becomes less important and the discomfort on the current path becomes more noticeable.

The mistake we made was thinking that the period from 1946 to 1980 was the norm. No, it was not! It was the anomaly!

Helping people live courageously so that they can thrive is one of the most important things in the world. I want to see people live the lives they are capable of, not just the ones they think they are allowed to live.

Uncertain Discomfort + Wonder > Certain Discomfort

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.

No money is worth it if it undermines your desire to stay on the journey.

encourage everyone to write a description of the person you don’t want to be, then brainstorm actions that might create that outcome.