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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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September 27th, 2024 | by Kyle Brennan
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Thought of the Week
Why You Hate Your Own Art (And Why That’s the Point)
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We’ve all been there. You pour yourself into something, step back to admire it… and cringe. It looks exactly like you made it.
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I used to feel this way about my writing. I thought if I just got better, my work would magically feel like someone else had written it. Maybe I’d wake up one morning and it would sound like Hemingway had taken over.
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But there's no level of skill beyond which you stop being you.
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In fact, that’s the whole point.
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By nitpicking and criticizing my own work, I was invalidating the most valuable thing about it: the part of it that came from me.
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That feeling never goes away. We're always chasing a better version of ourselves.
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But the goal isn’t to escape that chase—it’s to embrace it.
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What makes Mick Jagger Mick Jagger isn't his songs. It’s the swagger, the eccentric fashion, the way he moves and thinks. His art is an extension of who he is. That’s what people connect with.
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It's his swagger, his fashion sense, the way he speaks, the way he thinks, and how he embodies that in his music.
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We can’t objectively judge our own art. We can only do the art.
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Now, when I sit down to write, I don’t ask, “How can I sound more like Murakami or Michael Lewis?” I ask, “How can I sound the most like me?”
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Because that’s the part that matters most. And it's the part no one else can do.
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What I'm Reading
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While I’m not planning to launch a business right now, I know I’m sitting on a lot of potential with my blog, newsletter, social media, and podcast growth. I picked up The E-Myth Revisited from my dad’s shelf to get a better sense of what running a successful business really takes.
In this easy-to-read book, small business consultant Michael E. Gerber breaks down the myths of entrepreneurship. Many believe businesses are started by entrepreneurs chasing profit, but most are actually started by technicians—employees who decide to work for themselves. They may know their craft, but they often lack business skills. Gerber emphasizes that technical expertise alone isn’t enough to succeed.
What stood out to me most is that this book isn’t about turning a passion into self-employment. Instead, it’s about how to get your business to run without you. Gerber explains the importance of working on your business, not in it. He uses McDonald’s as an example, showing how its success came from building a franchise system, where the real product isn’t the hamburger, it’s the brand and customer experience.
Overall, the book reshaped my view of entrepreneurship. My only gripe is that Gerber can get a bit long-winded at times, but the insights were worth it.
Rating: 3.7 / 5 ⭐️⭐️⭐️
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As the saying goes, “Babies don’t come with instruction manuals.”
When my wife showed me the positive pregnancy test, I was filled with joy at the thought of becoming a dad. But soon after, the nerves kicked in. I knew nothing about pregnancy’s physical and emotional demands, let alone how to care for a newborn. As someone who likes to be over-prepared, I felt clueless.
Nowadays, there are countless resources for moms-to-be. For dads…here’s a pamphlet - “No cigars in the hospital. Try not to ruin your child’s life.”
Enter former NFL tight end and Super Bowl champion Benjamin Watson @benjaminswatson As a father of five, Watson saw countless teammates struggle to navigate the complexities of pregnancy, changing diapers, and transitioning from tough-guy NFL player to “Dad.” This book was gifted to me by a fellow reader and first-time dad, and I’m so grateful for the wisdom Watson lays out so clearly.
This book is a crash course in Fatherhood 101. It’s straightforward, skips the fluff, and covers everything a new dad might be unsure about - from taking care of your wife to bathing your baby for the first time. Watson writes for men who may not have the time, patience, or desire to read to be seen reading the frilly covers of traditional parenting books, which are often geared toward moms.
If you’re a first-time dad, this is the perfect playbook. It’s a must-have resource to help you feel more prepared for the journey ahead.
Rating: 4.5 / 5 ⭐️⭐⭐⭐️️️
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What I'm Watching
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Lauren and I were looking for a comfort-watch the other night and figured it was the perfect fall weather for a good Halloween movie. Say what you will about modern Adam Sandler movies, the guy knows how to put together an enjoyable film for all ages.
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Was this the funniest movie I've ever seen? No. But I got exactly what I was expecting - a silly comedy with good plot twists, good-feelings, a few corny jokes and a handful of hilarious one-liners.
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The cast is star studded with Ray Liotta, Kevin James, Julie Bowen, Steve Buscemi, and Noah Schnapp. It's also filled with a ton of nods to Adam Sandler classics like Billy Madison and Happy Gilmore, which I appreciated.
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These types of movies are what I call "perfect plane movies." Meaning, they're not blockbusters or Oscar winners, but they're great for a mindless 90-minute distraction on a quick flight to a nearby city.
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Quote I'm Pondering
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"Change. But start slowly, because direction is more important than speed."
-Paulo Coelho
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Keith and Kyle sit down to discuss the concept of "Inverted Totalitarianism" in Sheldon Wolin's book "Democracy Inc.", the top 5 comedic acting stretches, how getting older and having children changes your perspective on life, and Keith performs a scene by memory from the classic comedy "Tommy Boy."
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Books discussed in this episode:
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Check Out 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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