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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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January 24th, 2025 | by Kyle Brennan
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Thought of the Week
Why Your Habits Should Raise Eyebrows
If no one questions your daily habits, you're probably doing it wrong...
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Ok, I'll admit. I wrote that title and opening line to be a bit provocative.
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Obviously, one can have perfectly "normal" habits and still be successful. This isn't my way of saying one must cold-plunge themselves to wealth and happiness.
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Rather, my point is that greatness has a way of making people uncomfortable.
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It forces others to question their own routines, excuses, and choices.
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And that’s a good thing—for you and for them.
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- Why are you eating that?
- Why are you waking up at 5 a.m.?
- Why are you so obsessed with improving yourself?
Because I care.
Because I refuse to settle for average.
Because I want to see what happens when I aim for the top 1%.
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Here’s the truth: people doing less will always have the most to say. They’ll mask their insecurity as criticism, trying to drag you down to their level. But the ones doing more? They’ll never judge you. They’ll nod, silently recognizing a fellow traveler on the path of self-mastery. There's a certain informal respect amongst the 5 a.m. gym crowd.
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Stop seeking validation from the crowd. The crowd isn’t coming.
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Instead, be the person whose discipline and focus make others squirm. Not out of malice, but because your example forces them to reflect on their own untapped potential.
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Discipline isn’t for everyone—and that’s the point. It’s not supposed to be.
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The question is: are you brave enough to make people uncomfortable?
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Make decisions that scare you.
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Take actions that separate you.
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Build habits that change you.
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What I'm Reading
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This book has been on my radar for a while. It’s frequently listed as one of the top non-fiction books of all time and yet I had never come across it in all my years scanning libraries and bookstores. Finally, I decided to pick up a copy, and within two days, I devoured its concise yet profound 100 pages. Now I understand why this book is considered essential reading.
The Lessons of History is a masterclass in brevity and depth, distilling the vast expanse of human experience into its most critical insights. Written over 50 years ago, it still holds its ground against modern classics like Jared Diamond’s Guns, Germs, and Steel and Yuval Noah Harari’s 21 Lessons for the 21st Century. These contemporary works echo many of the Durant’s themes—urging us to approach history with skepticism and caution, warning that history’s complexity allows “a case for almost any conclusion… by a selection of instances.” Yet it’s clear that both Diamond and Harari owe a debt to the intellectual groundwork laid by the Durants.
In just a few pages per chapter, the authors cover a staggering array of topics—religion, race, war, economics, progress, and decline—analyzing the entirety of human history with remarkable clarity. Their prose often reads like poetry, elevating the mundane into the universal. Through their lens, our present-day challenges reveal themselves as age-old problems dressed in modern garb, reminding us that history repeats not in exact patterns but in persistent themes.
The beauty of this book lies in its openness to interpretation. The past offers lessons for everyone, but what we take from it depends on our perspective. If you seek hope, history provides plenty. If you’re inclined toward cynicism, history can validate that too. The Durants challenge us to approach history with wisdom, choosing lessons that not only guide us through the present but also help us leave a richer legacy for future generations—generations that will one day see us as mere pages in their history books.
Rating: 4.8 / 5 ⭐️⭐️⭐️⭐️
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Comfortable Shirts I'm Wearing
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At $178, these shirts are ridiculously expensive, which is why I would never recommend buying them at full retail price. I have, however, bought several of these shirts on secondhand sites like eBay and Poshmark, where you can get them for roughly a third of the price. They are insanely comfortable.
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Article I'm Reading
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However you feel about Donald Trump, I feel like this article by Salena Zito provides an interesting glimpse into our current president's personal and political life.
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Salena Zito was one of the few reporters who followed Trump's rise in 2016 and predicted his win in the election.
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She also popularized the phrase coined by Republican strategist Brad Todd that I think sums Trump up perfectly:
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“The press takes him literally, but not seriously; his supporters take him seriously, but not literally."
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What I'm Watching
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Lauren and I saw Ari Shaffir perform last summer in NYC and thought he was hilarious. In his new special, he aims to shed light on all of the positive messages we should be taking away from all of the negativity circulating in modern society.
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Also, if you haven't seen his earlier special, Jew, on YouTube, I can't recommend it enough. Ari grew up as an Orthodox Jew and spent two years studying at Yeshiva in Jerusalem, so the entire hour is as much an education about the Jewish faith as it is hilarious stand-up comedy.
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What I'm Listening To
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Trigger warning: this episode and the content discussed are highly controversial, especially for parents.
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In this episode, Tim, Naval, and Aaron discuss the "sovereign child" approach, which flies in the face of most modern parenting advice, a la Dr. Becky Kennedy. Most of which, I find highly contentious, but nonetheless interesting to conceptualize.
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In short, The Sovereign Child introduces a bold parenting philosophy centered on 'voluntary rules,' allowing children the freedom to choose their own schedules while providing a loose framework for safety and interaction—a concept that balances independence with structure but may challenge traditional notions of parenting.
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Quote I'm Pondering
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If you spend enough time reading or writing, you find a voice, but you also find certain tastes. You find certain writers who when they write, it makes your own brain voice like a tuning fork, and you just resonate with them. And when that happens, reading those writers—not all of whom are modern... I mean, if you are willing to make allowances for the way English has changed, you can go way, way back with this—becomes a source of unbelievable joy. It's like eating candy for the soul.
And I sometimes have a hard time understanding how people who don't have that in their lives make it through the day.
—David Foster Wallace
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Note from Kyle: Keith and I have been on a bit of a hiatus between vacations and babies, but we will be recording episode #37 sometime next week hopefully! Check out our latest episode in the meantime!
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Keith and Kyle sit down to discuss the recent unexplained drone sightings around the country, Søren Kierkegaard's philosophy, social bubbles, and the story of "The Wager."
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Books discussed in this episode:
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Top Books of 2024
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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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