Hi Reader, Happy Labor Day weekend! If you're at the US Open, I hope you're enjoying those Honey Deuces (which btw generate $10mm in sales). A friend with a great finance job recently told me: “I’m the type of tired that a vacation doesn’t fix.” He'd gotten to the point in his career where he had a reasonable boss, a team that delivered and could sleep 7 hours a night. But it wasn't that kind of tired. "My soul is tired." I know there are a lot of tired souls reading this. Maybe it's the lack...
8 days ago • 3 min read
Hi Reader, Last call for white linen paths! I hope everyone enjoys the last week in August. My friend (and frequent podcast guest) Joe Hudson is an incredible coach and teacher. He's a former VC who guides professionals on deeply introspective journeys. Together on our podcasts, we've tackled envy, scarcity thinking, perfectionism and the fierce inner critic. Joe takes a unique approach to personal growth, drawing from several spiritual, psychological, and neurological practices. His upcoming...
15 days ago • 3 min read
Hi Reader, I can't believe the kiddos start school this week. But let's be honest, a little structure probably ain't a bad thing. Speaking of fatherhood, I often wonder if I'd be a better parent if I was less ambitious. Hear me out, I know my drive has created a wonderful life for my family. But I can easily tip into the land of unhinged ambition - and then become distracted and disconnected. My friend Jeff Hittner (who wrote this week's essay) is organizing a free workshop for Ambitious Dads...
22 days ago • 3 min read
Hi Reader, I've been absolutely loving these olympics. Chef Curry against Serbia. Gabby Thomas (even though she went to Harvard). "Raygun" the break dancer. Oh and the infamous "pole" vaulter. BTW, are you an ambitious dad who wonders if you're doing this whole "fatherhood" thing right? If you're struggling to be present, patient and intentional as a father we have a free workshop for you on August 21st. Sign up for the free Ambitious Dads Workshop→ Burn all the ships (and go for gold) There...
29 days ago • 3 min read
Hi Reader, Happy August! I gotta say the Olympics have been awesome - pommel horse guy, the pistol shooters and ofc Snoop Dogg yucking up at all the main events. If there was a productivity olympiad, you'd definitely want to be using our $10K Work framework for maximum leverage and deconstructing the "why" behind your goals. Supercharge Your Productivity is the only course that connects the pursuit of productivity to life's larger questions. Get Supercharge your Productivity → The "messy...
about 1 month ago • 2 min read
Hi Reader, I’m in NYC this week to see family, friends, clients (and a Justice concert). And the weather's been delightful. We're rounding up our last group coaching cohort of 2024. If you're a high-earner who's looking to make a bold pivot (but scared to take the leap), this 5 person group is for you. We've had folks take sabbaticals, go hard on a side-project and confidently walk away from unvested stock. What did these professionals all have in common? A commitment to no longer living the...
about 1 month ago • 3 min read
Guess what's sexy these days? Cargo pants. Chunky sneakers. And buying boring businesses. Yup. Folks are ditching their fancy Wall Street and FANG careers to buy... wait for it... Laundromats, pest control services and plastic bag manufacturers. This week on The Examined Life Podcast, we’re joined by former hedge fund investor and small business owner Ben Jasper. We ask the question: Should you buy an unsexy business? (Watch on YouTube) 🎧 Or listen on Spotify, Apple Podcasts or your favorite...
about 1 month ago • 2 min read
Hey Reader, I hope you’re having a rad start to the weekend. My friend (and podcast guest) Nat Eliason just wrote the ultimate beach read. I rarely read non-fiction, but devoured Crypto Confidential in one sitting. Y’all know I don’t really care much for crypto — what makes the book so dope is how it exposes the sketchiness, the massive wealth creation (then destruction) and how one man (Nat) thought it would be his young family’s lottery ticket towards financial independence. Get Crypto...
about 2 months ago • 2 min read
On Monday, I turned 45. I’ve lived 60.3% of my lifespan. I have way less hair. But at least I’ve held on to my six pack. I left Wall Street so that I could have time freedom, raise my kids and surf every day. And I learned a few lessons along the way. I’ll share 45 of them on workaholism, borderline alcoholism, finding aliveness, taking a huge pay cut and what to do when you find your favorite t-shirt. This week on a solo episode of The Examined Life Podcast, Khe answers the question: What...
about 2 months ago • 2 min read