I’m passionate about helping people imagine new stories for work & life
I’ve been wandering a “pathless path” for seven years, and am deeply curious about our modern relationship with work. I write, share ideas, have conversations, and experiment with my own life.
I write a weekly newsletter that goes out to 23k+ people
My book, The Pathless Path, has sold 50k+ copies
“I just finished the last 100+ pages this morning and I can confidently say that this is one of the best non-fiction books I’ve read in my life.”
Justin Welsh, Solopreneur & Creator
I hadn’t prioritized reading it since I assumed I’d know what it was about from his newsletter, but no… this is polished and fresh content. It really should be a mainstream airport bestseller type book, not niche subculture blogger self-published book.
Venkatesh Rao, Writer at Ribbonfarm
Recent Writing
The Long 2024: A Year of Change, Creativity, and Letting Go
2024 was a year of liminality. Our last full year in Austin, not knowing where we’d go afterward or when we’d leave. A year of deepening into fatherhood, finding my creative groove again, and then losing it. A year of supporting Angie’s creative awakening and laying the foundation for what’s … Read more
Book Review: “The Organization Man” – How the 1950s Shaped Our Work, Lives, and Aspirations
Reading William Whyte’s 1956 classic, “The Organization Man,” feels like uncovering the source code for much of modern white-collar life. Compiled from his writings in the 1940s and 50s, the book dissects an emerging phenomenon he termed the “social ethic” – a belief system prioritizing the group, belonging, and the … Read more
Hacking US Healthcare: A Guide to US Healthcare for Self-Employed People
Over the last eight years, I’ve directly experienced the US healthcare system from multiple angles. As a self-employed person, I’ve had health insurance in four different states (NY, MA, CT, TX), been uninsured for multiple years, interacted with healthcare systems in Mexico, Taiwan, Spain, and Portugal, and have had multiple … Read more
What if everyone followed The Pathless Path?
People often ask me, “Is your advice useful for most people?” and “If everyone followed your path, wouldn’t society fall apart?” I reject both of these frames. First off, I write, create, and share from my own perspective. I don’t write trying to give advice, to build a massive following, … Read more
Rethinking Wealth: Four Insights from “Just Keep Buying”
Personal finance advice often feels like a maze of contradictions. Save everything. Live a little. Invest aggressively. Play it safe. After years of grappling with these mixed messages, I found clarity in Nick Maggiulli’s “Just Keep Buying.” Through its data-driven insights, I discovered a more nuanced – and ultimately more … Read more
Question People and Answer People
Someone said to me once, “there are things people, people people, and ideas people.” I instantly knew I was an ideas person. I love discovering new ideas, going down strange rabbit holes, trying to come up with better ideas for my life, talking about ideas, and finding others who are … Read more
How to answer “what do you do?” on a pathless path
I was at a gathering on Thursday and someone asked, “What do you do?” Given that I was in Austin, I thought I could share the real story: “writing online, podcasting, internet things, you know.” It was a creator’s hangout after all. “What do you write about?” he followed up. … Read more
The Case For Quiet Quitting (and the dangers of slacking at work)
Vox published an essay in 2023 about the people who do little to no work at their jobs. The article, “How some people get away with doing nothing at work,” seems to fit into the coordinated “return to office” campaign across the mainstream news. The title seemed a bit weird … Read more
Escape Shouldandia!
As someone that enjoys writing and does so consistently, a lot of people tell me about their own relationship with writing. Many people wish they wrote more. They tell me some form of, “I should write more,” or “I need to write more.” They live in a world I call Shouldlandia. Inhabitants … Read more
Solopreneur & Creator Week-In-The-Life (as a parent)
For more than seven years since 2017, no week has looked the same. Most days don’t look the same either. But generally, the mix of activities and how I feel about them does feel somewhat the same. This is probably what makes me feel more “stable” on this path than … Read more