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Three Books for the Next Phase

Дата публикации: 22-03-2026 19:15:59

I read three books yesterday that have nothing to do with each other on the surface. One is about founder mental health. Another is about monks who hike. The third is about quitting your job and figuring out what comes next.

Основное содержимое страницы с новостью.

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.

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