Three Books for the Next Phase

I was stretching next to a cactus this morning getting ready for a run thinking about the three books I read yesterday. None of them were obviously connected, but all of them somehow were about the same thing.

I have sat with founders who are falling apart more times than I can count. Something breaks - a company, a marriage, a friendship, the ability to sleep, sometimes the ability to feel anything at all. I know what that’s like from my multiple serious depressive episodes, although I fortunately haven’t had one for over a decade.

James Oliver Jr. has been alongside founders in this territory for years. His book Burn Bright, Not Out - co-authored with Django De Gree - is what I wish had existed a long time ago. James didn’t write a self-help book. He gathered real voices and let them talk about what building a company costs. The Kabila Founder Mental Health Fund that James runs - free therapy for founders who can’t afford it - is something I would have pointed people toward during the hardest stretches I’ve witnessed.

I love to run. As I get older and slower I’m learning to love hiking more. When I saw Hiking Zen: Train Your Mind in Nature by Brother Phap Xa and Brother Phap Luu - two Buddhist monks ordained by Thich Nhat Hanh - in Greeley Sachs’ Composition Shop bookstore, I knew I had to read it. I have a soft spot for monks.

The book isn’t about covering miles or conquering peaks. It’s about what happens when you pay attention on a trail. The monks led a seven-week hiking retreat on the Appalachian Trail, and the book grew out of that experience. Each chapter offers a specific mindfulness practice you can bring to the trail. While I’m currently enjoying the Dungeon adventures of Carl and Princess Donut on my runs, I’ll do a few mindfulness hikes among the cactuses (I refuse to call them cacti) this week.

Paul Millerd sent me a copy of The Pathless Path: Imagining a New Story For Work and Life. I don’t think I know Paul, but the phrase “default path” - the one that runs from graduation to career to retirement without ever asking why - hit me immediately.

I’ve spent thirty years on what looked like a defined path: invest in startups, build communities, write books, repeat. But the path I’m on now doesn’t have a name. I’m focused on non-attachment (not detachment, which is different) to everything, including success, progress, and a path itself. Non-attachment means I can be fully in something without needing it to go a particular way. The default path requires attachment to every milestone. Paul’s book reinforced the framing for what I’ve been doing.

After a delightful digital sabbath with books, I’m back to playing with Lumen.