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The Observe and Rapport Newsletter
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A weekly guide of my favorite books, articles, products, and lifestyle habits.
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November 22nd, 2024 | by Kyle Brennan
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Thought of the Week
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...almost nothing important that ever happens to you happens because you engineer it. Destiny has no beeper...
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Translation: You can't schedule serendipity.
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It's a reminder that, sometimes, the most life-changing moments unfold when you're not micromanaging the universe like a stressed-out micro-manager.
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Alan Watts talks about this as "The Art of Sailing vs. Rowing."
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One uses flow, the other uses force.
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Life's big wins often come when you're in "sailing mode"—trusting the process, staying present, and knowing when to let go. Whether it's a career move, a relationship, or jiu-jitsu (shout-out to my fellow grapplers), forcing it almost always backfires.
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Sometimes, you’ll get where you want to go faster by... well, not trying so damn hard.
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What I'm Reading
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The “Hero’s Journey,” is a universal template for storytelling. Basically, every epic tale—whether it’s Star Wars, Lord of the Rings, or The Lion King—follows the same general script. The hero starts in their ordinary world, gets called to adventure (sometimes reluctantly), faces trials, meets a wise mentor, defeats the big bad, and returns home, transformed.
This isn’t just some half-baked theory. Campbell spends hundreds of pages showing how myths, religions, and legends from around the world—Greek, Hindu, Native American, Norse, you name it—fit this mold. And while it’s fascinating, it can also feel like you’re reading the world’s longest Wikipedia rabbit hole. One minute he’s talking about Odysseus, and the next he’s diving into dream analysis with Freud and Jung. If your head starts spinning, don’t worry—it’s normal.
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- The Call to Adventure: This is where the hero’s ordinary life is disrupted. Think Neo choosing the red pill or Harry Potter getting his Hogwarts letter.
- The Road of Trials: A series of tests, challenges, and mini-bosses the hero must face to grow stronger. It’s basically the montage scene in every movie ever.
- Atonement with the Father: A weirdly specific step where the hero reconciles with some kind of authority figure—either literally or symbolically. (Spoiler: Daddy issues are a global theme.)
- Return with the Elixir: The hero doesn’t just survive; they bring something valuable back to share with their community—knowledge, power, or the Infinity Gauntlet.
To be honest, I gave up on the book about halfway. It’s dense and difficult to follow. He was trying to name the one great mega-myth at the core of all religions and mythologies, but I think he got carried away trying to explain everything with one insight.
This book is the basis for something like 95% of modern fantasy, so if you’re a writer or filmmaker, it may be worth giving it a read. However, if you want to make the next great fantasy novel, just rip off Harry Potter instead of slogging through this. The end result will be the same.
Rating: 2.4 / 5 ⭐️⭐️️
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Articles I'm Reading
Nabeel is currently a stealth startup founder but was previously at Palantir. He has been a visiting scholar in AI at the Mercatus Center as well as an Emergent Ventures awardee. Some of my favorite principles from the list:
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- If you don’t “get” a classic book or movie, 90% of the time it’s your fault. (It might just not be the right time for you to appreciate that thing.)
- Form opinions on things and then find the strongest critique of those opinions. Repeat.
- Don’t “slow down” as you get older, speed up. Lean into changes, be curious about new things. Most people seem to go the other way.
Trust in the media has declined drastically for obvious reasons. A few key reminders when reading articles from mainstream media:
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- Any headline that ends in a question mark can be answered by the word no.
- The amount of energy needed to refute bullshit is an order of magnitude bigger than to produce it.
- As an online discussion grows longer, the probability of a comparison involving Nazis or Hitler approaches
- If a writer refers to something as "fringe," it the subject likely just isn't popular amongst elite society
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The first round of tossings into the lizard-pit will involve “experts” who still use grossly snobbish terms like “fringe” and “contrarian” to describe beliefs held by most of the population:
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What I'm Watching
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After binge-watching all 16 seasons of Always Sunny multiple times, I'll watch pretty much anything Glenn Howerton touches.
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A.P. Bio is all about a disgraced Harvard professor, Jack Griffin, who gets stuck teaching high school biology but refuses to actually teach—he’d rather use his students to pull off petty revenge schemes and feed his massive ego.
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Howerton’s characters Dennis Reynolds in Always Sunny and Jack Griffin in A.P. Bio are like two sides of the same egotistical, morally questionable coin. Both are delusionally self-assured and obsessed with their own perceived superiority.
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The show is dark, snarky, and full of absurd humor - but with just enough heart to keep you rooting for the chaos.
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My Latest Scribbles
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What I'm Listening To
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Some argue that jazz is the quintessential American sound, but to me, the blues has a rawness and emotional depth that laid the foundation for so much of what came after. It’s the backbone of rock, soul, and even hip-hop. Without the blues, there’s no Elvis Presley, Chuck Berry, or The Rolling Stones. Even today, artists like Adele, Jack White, and Chris Stapleton weave influential blues roots into their songs.
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Blues music started in the Mississippi Delta in the late 19th and early 20th centuries, born out of African-American spirituals, work songs, and chants. As African Americans began moving to northern cities, the blues evolved. Electric guitars and amplifiers gave us Chicago Blues, with artists like Howlin’ Wolf and Buddy Guy. By the time the 60s rolled around, British rock bands took these sounds and repackaged them for a global audience.
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This song by Mississippi Fred McDowell (great name) is a beautiful timepiece of that raw grit of true Southern blues. Gives me goosebumps.
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Quote I'm Pondering
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“It is impossible to get better and look good at the same time. Give yourself permission to be a beginner.”
— Julia Cameron, The Artist’s Way
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Keith and Kyle sit down to discuss the atmosphere, results, and potential political, cultural, and governmental reformations set in motion by the most recent presidential election.
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On next week's episode, we invite comedian/filmmaker (and my college roommate) Kyle Mara to discuss his new YouTube special, "Jokes on the Upper East Side"
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My Amazon Favorites Bookstore
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Browse my favorite book selections hand-curated by me. I also earn commissions so if you buy anything, those earnings get reinvested right back into this fancy newsletter ;)
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Affiliate Links!
I've had the fortunate opportunity to partner with some great brands that I love. Use the links below to find great hats, sweatshirts, and sunglasses
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- Huega House - 15% off first order with promo code: KYLEBRENNAN. My everyday hat is the Athletic Association in Green & white
- Find the Good Brand - 10% off first order with promo code: OBSERVE. I've been loving my 3 Simple Words Embroidered Hoodie in cream.
- WMP Eyewear - Excellent array of eyeglasses and stylish sunglasses. My favorite are the Sawyer Polarized for $45
- Amazon Storefront - Check out my collection of favorite books, workout gear, and tech tools for work-from-home!
- LMNT - I start every morning with LMNT's electrolyte drink, filled with salt, magnesium and potassium. It tastes delicious and contains zero sugar or any other junk. Try LMNT Risk-Free with a free sample pack (US only).
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33 Life Lessons on My 33rd Birthday
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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 for the role for over …
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Depth Over Downloads: Why Spending Time with Books Still Matters
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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 Klein admitted he once believed …
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The Jack Reacher Approach to Never Being Caught Off Guard
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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 Reacher. He’s not your typical …
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