by Kyle Brennan
Thirty-three was a big one. Mostly because I became a dad. Our daughter was born on New Year’s Eve — a fitting arrival for a kid destined to reset everything. It’s been a beautiful, if slightly sleep-deprived blur ever since. I’ve only been “Dad” for less than ten months, but if I’m being honest, I’ve been preparing …
Everyone wants faster information. But no one asks if faster information leads to better understanding — or a better life. In the age of AI and tweet-sized wisdom, we’ve confused information with transformation. But there’s a massive difference between knowing what a book says and being changed by it. The Delusion of Instant Learning In a recent interview, political journalist Ezra …
Continue reading "Depth Over Downloads: Why Spending Time with Books Still Matters"
There’s no difference between a pessimist who says, ‘Oh, it’s hopeless, so don’t bother doing anything,’ and an optimist who says, ‘Don’t bother doing anything, it’s going to turn out fine anyway.’ Either way, nothing happens.” —Yvon Chouinard, Founder of Patagonia I don’t read much fiction, but I’ve always been hooked on Lee Child’s Jack …
Continue reading "The Jack Reacher Approach to Never Being Caught Off Guard"
In the movie, The Truman Show, the main character, Truman Burbank, lives inside an artificial world — a giant movie set where everything, from the streets to the sky, is carefully controlled. At one point, a journalist asks the show’s creator why Truman never realizes the truth. The producer replies: “We accept the reality of the …
2024 was a year of big wins and even bigger wake-up calls. I got promoted, earned my blue belt in Brazilian Jiu-Jitsu, became a fully certified volunteer firefighter, broke 80 in golf for the first time, and — most importantly — welcomed my daughter into the world on New Year’s Eve. Not a bad highlight …
A man once asked a gardener why his plants grew so beautifully. The gardener said: “I don’t force them to grow. I remove what stops them.” Sometimes the smartest move is knowing what not to do. Success is often about sidestepping stupidity. First, do no harm. Why the Best Investors Think in Reverse Warren Buffett, …
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The best way to free up your time in 2025? Stop doing things you suck at. Take vacations, for example. For years, I stressed myself out trying to travel hack like a pro. I’d sit through dinners with friends who’d brag about flying to Europe for free — maxing out their credit card points, gaming …
Continue reading "The Subtle Art of Selective Sucking (Calm Down, It’s Not That)"
Sometimes, you make a decision that even you can’t explain — but in 2022, I found myself doing just that. For most of my life, I’d wanted to serve in some way, though I wasn’t exactly sure how. At one point, I even dreamed of joining the military, and still feel a hint of regret …
Continue reading "Into the Fire: Takeaways from Two Years as a Volunteer Firefighter"
I started Observe & Rapport when I was 25 years old. This week I turn 32. The original idea wasn’t to create a “brand” or be an “influencer” (much as my friends and family like to jibe), but rather to build a space where I could explore my unconventional interests and share them with whoever …
Last December, I was hanging out with some friends when my buddy Keith mentioned he’d been training Brazilian Jiu-Jitsu for a few months. My ears perked up. I had never tried any martial art before, so I had no idea why I was intrigued. But I’ve always been curious, willing to experiment — especially after hearing so …
Continue reading "Tapping In: A Year of Jiu-Jitsu and New Perspectives"