What 18 Years of Annual Reviews Taught Me: A Live Q&A
I went live to answer your questions about my new book, Life in Perspective. Here are my best answers in writing, plus the full replay.
Personal growth
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What I’ve Learned from 4 Years of Hosting Mastermind Retreats
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…
Operation Gallavant: An Overlanding Journey Through Latin America
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…
The History Beneath My Feet: Two Years in Valle de Bravo
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…
5 Questions to Help You Navigate Uncertainty
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…
Groundbreakers 2: Seeking the Heart of Fear
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…
How to Create Your Own Luck: 5 Easy Practices
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…
My 2025 Annual Review
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!…
What I’ve Learned From 20 Years of Goal-Setting
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…
Beyond Acceptance: The Transformational Journey of Applying to Grad School (or Anything Else)
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…
A Brief History of the Annual Review
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…
My 4-Stage System for Learning Anything New
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…