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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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December 27th, 2024 | by Kyle Brennan
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Thought of the Week
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“The man who needs a new machine tool and hasn’t bought it is already paying for it.”
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Warner & Swasey was a well-known US tool hire company. In the 1950’s they ran an advert with the tagline, ‘The man who needs a new machine tool, and hasn’t bought it, is already paying for it.’ Charlie Munger, Warren Buffet’s business partner at Berkshire Hathaway recalled the line and underlined the truth of it.
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When we delay making an important decision or investment (especially one that could make life a little bit easier), we end up paying the cost in other ways.
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Imagine you’re a student who needs a new laptop for schoolwork. Your current one crashes all the time, and you spend hours trying to fix it or redoing assignments that get lost. You might think, “I can’t afford a new laptop right now,” but in reality, you’re already paying for it — with your time, stress, and possibly lower grades.
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Sometimes investing in the right tool, support, or decision now is the best way to stop the invisible costs from piling up.
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What I'm Reading
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Derek Sivers is one of the most fascinating thinkers I’ve come across, and I’m constantly surprised he’s not more widely known. His wisdom is broad yet compact, delivered in bite-sized, impactful sentences across his short-form books.
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His latest book, How to Live, tackles one of life’s most profound philosophical questions: What constitutes a good life? Rather than offering a single definitive answer, Sivers embraces exploration. The book’s central premise is that there isn’t one “right” way to live—it’s all about discovering what works for you and staying flexible as your circumstances and values evolve.
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Sivers presents 27 deliberately conflicting answers to this question, exaggerating each lifestyle to reveal both its appeal and its flaws. By design, these contradictions highlight the dangers of following any one philosophy to the extreme, bringing clarity through intentional confusion. Each chapter is lean, with no wasted words—a collection of distilled insights rather than verbose explanations.
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At just 127 pages, the book reads like the highlights of a larger, more traditional work. Its chapters, often structured in brief, Haiku-like paragraphs, pack an intellectual punch that leaves room for the reader’s own reflection. Another reviewer aptly called it a “modern-day Meditations,” which I think it a perfect comparison.
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Some of my favorite insights from the book:
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- “Silence is the only way to hear quiet wisdom.”
- “Places don’t make emotion. You do.”
- “Today’s discomfort brings future rewards.”
- “To enjoy your past is to live twice.”
- “Pain is coming anyway. Don’t get a shield. Get a saddle.”
The book’s contradictions might leave readers agreeing with only a handful of its ideas—and that’s perfectly fine. It’s not about prescribing a singular path but about exposing different perspectives and possibilities. This approach invites readers to ask themselves the most essential question: How do I want to live?
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In my opinion, asking that question is the only true beginning to living a good life.
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My Latest Article
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The best way to free up your time in 2025?
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Stop doing things you suck at.
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The idea of “Selective Sucking” has become a mental framework for me. Life is a game of trade-offs. You can’t excel at everything, so you might as well get intentional about where you’re willing to fall short.
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Read the full article here.
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What I'm Watching
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Aaron Rodgers is undoubtedly one of the greatest football players of all time. He's also one of the most controversial.
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If you only watched sports talk shows you'd assume he's a cocky anti-vaxxer who disowned his family. But as is always the case, there's a lot the media gets wrong about him.
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This three-part documentary covers Aaron Rodger's career, the tragic injury during his NY Jets debut, and his journey into plant medicine and spirituality. I always enjoy these behind-the-scenes profiles of public figures who are wildly misunderstood. It gives us a glimpse into the human behind the superstar, warts and all.
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What I'm Listening To
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I love listening to Dr. Gabor Maté (@gabormatemd). His insights and clarity on trauma, addiction, childhood development, stress and healing are unmatched. I've read several books on these topics, but Maté can distill years of research into a sentence or two.
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"Addictions are a response to immense emotional pain that [one doesn't] know how else to handle... The more you suffer, either socially or individually, the more likely you are to escape in the soothing and the relief that drugs or other addictions offer. So if you look at [the average] American in society, you're going to be asking, why are so many people having to escape from reality?"
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My Favorite Podcast Episodes of 2024
According to my Spotify Wrapped, I spent 31,310 minutes listening to podcasts this year - which equates to about 22 straight days of my life. Thankfully, it wasn't all for nothing. I learned some interesting stuff during my long walks. Here are the most interesting and thought-provoking episodes I listened to.
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- Casey & Calley Means: The Truth About Ozempic, the Pill, and How Big Pharma Keeps You Sick - The Tucker Carlson Podcast
- #2234: Marc Andreeson - The Joe Rogan Experience
- #878: David Senra - 15 Harsh Truths From History's Greatest Founders - Modern Wisdom
- #454 - Saagar Enjeti: Trump, MAGA, DOGE, Obama, FDR, JFK, History & Politics - Lex Fridman Podcast
- The Divorce Expert (James Sexton): Slippage is Tearing Marriages Apart! If Kids Are Your Top Priority & You Spot This You'll Divorce in 1-3 Years! - The Diary of a CEO w/ Steven Bartlett
- The Investing Expert (Scott Galloway): We're Raising The Most Unhappy Generation in History! The Unseen Link Between Marriage & Wealth! Hard Work Doesn't Build Wealth! - The Diary of a CEO w/ Steven Bartlett
- #830 Alex Hormozi: 24 Controversial Truths About Success & Failure - Modern Wisdom
- #2208 Brigham Buhler - The Joe Rogan Experience
- E477 Tony Robins - This Past Weekend w/ Theo Von
- The Investing & Crypto Expert (Raoul Pal): "We Only Have 6 Years Until Everything Changes!", The S&P 500 Isn't Worth Your Time!" - The Diary of a CEO w/ Steven Bartlett
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Quote I'm Pondering
Thomas Sowell on Capitalism:
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It is not an 'ism.' It is closer to being the opposite of an 'ism,' because it is simply the freedom of ordinary people to make whatever economic transactions they can mutually agree to.
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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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