On January 8, 2023, I sent the following message in a WhatsApp group chat: This message emerged from my annual review that year, completed just a couple days before, in which I decided I needed more community in my life after years of working in isolation during the pandemic. To my utter surprise, about 10…
I’m incredibly excited to inaugurate a new project I’m calling Operation Gallavant: a multi-month family road trip we’re planning on taking down the length of Central and South America. This is something I’ve wanted to do for many years. Ever since I was a child, we’d regularly visit my Brazilian family via a 12-hour flight…
I’ve been living with my family in a Mexican mountain town called Valle de Bravo for almost two years now, and I’ve found it to be one of the most special, unique places I’ve ever spent any length of time. The natural environment, the culture, the people, and the perspectives it offers have taught me…
In the early 2010s, the gaming startup Tiny Speck was a darling of the tech industry. The company had raised $17 million. The launch of its first game, Glitch, was covered by international media, including The Guardian and The New York Times. Within months of launching, it had tens of thousands of active players. But…
Six years ago, I attended a week-long course in Northern California called Groundbreakers. Facilitated by Joe Hudson and his wife, Tara, it was one of the most impactful experiences of my life. The experience I had there reshaped my relationship with the “voice in my head,” that is, with my own inner monologue. It helped…
You’re scrolling LinkedIn during a coffee break. A course creator you know just hit $100K in their first cohort. Another founder you know just closed a funding round. And a peer you met at a workshop got invited to speak at the conference you’ve been attending for years. “They’re so lucky,” you think, closing the…
At the start of 2025, I dubbed this “The Year of Profitability,” and now that it’s come to a close, I can say we successfully fulfilled that intention. We ended the year with 2.15M in gross revenue, and $650,000 in net profit, for a 30% gross margin. That’s our second-best year ever as a business!…
In the summer of 2005, when I was 20 years old, I sat down and wrote one of my first personal goals: “Hold a position in the Associated Student Government of Saddleback College at start of Fall semester (August 22, 2005).” I had just dropped out of college on the East Coast after burning through…
My wife Lauren and I met at a co-working space in San Francisco in our mid-twenties. I was working an entry-level position at a creative consulting agency, at the bottom of the pyramid. Lauren was making $15/hour at an arts nonprofit, living rent-free with her aunt. We both saw no pathway to climb in our…
When I began writing my next book more than a year ago, on the topic of “annual life reviews,” I assumed that the practice was a fairly recent invention. Maybe it came from the self-help movement of the 1970s. Or from corporate performance reviews. At most, I figured it might trace back to Ben Franklin…
You discover something fascinating—maybe it’s vibe coding, sustainable investing, or sourdough baking. Your excitement builds as you imagine mastering this new skill. But then reality hits: Where do you even start? The internet offers endless tutorials, courses, and “ultimate guides.” Your bookmarks folder grows heavy with resources you’ll “definitely check out later.” Weeks pass, and…
I spent 2 years serving as a Peace Corps volunteer in Eastern Ukraine from 2009 to 2011. I lived in the town of Kupyansk, a couple hours outside Kharkiv, near the Russian border. It was one of the greatest experiences of my life, teaching me so much about myself and life and the people and…