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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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February 28th, 2025 | by Kyle Brennan
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Thought of the Week
The Cost of Being Cheap
Research by George Loewenstein and colleagues found that spending money well is a skill—one that a shocking number of people do badly.
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The obvious offenders are the ones who blow their paychecks on bottle service and swipe their credit cards with reckless abandon. These are the Spendthrifts who book last-minute flights to Ibiza but think a 401(k) is a discount code for online shopping.
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But while this group gets most of the attention, the silent sufferers are those who clutch their wallets so tightly they never let themselves enjoy the fruits of their labor.
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Meet the Tightwads—I'm sure we all know someone like this. They skip the dinner with friends, avoid upgrading the shattered iPhone, and pass on the once-in-a-lifetime concert—all because the simple act of parting with their money is so painful.
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I know this because I used to be one of them. In my early twenties, I was great at saving. So good, in fact, that I missed out on experiences I could have easily afforded. In hindsight, I'm glad I built myself a comfortable nest egg, but I more so regret playing things too safe. I treated money like something to hoard, not a tool to build memories.
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If that was true then, it’s probably true now. Fears can protect us, but they can also confine us.
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The trick is balance. If you’re the type who spends too freely, a little financial restraint is wise. But if you’re the type who winces at every transaction, consider this: Money exists to be used.
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The goal isn’t to die with the biggest number in your bank account. It’s to translate that number into a life well lived.
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What I'm Reading
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I had no idea how much influence a small, scrappy group of people had in shaping the American identity. Born Fighting by Jim Webb chronicles the journey of the Ulster Scots—also known as the Scots-Irish—across centuries, from the borderlands of Scotland and Ireland to the Appalachian hills of America.
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Webb, a soldier-turned-Senator-turned-author, argues that the Scots-Irish mindset—fiercely independent, tribal, and action-oriented—was forged in centuries of conflict and migration. They were the anti-establishment rebels long before that became a brand, clashing with British aristocrats, shaping frontier culture, and leaving an outsized mark on American history.
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The book takes us through key moments like Hadrian’s Wall, Robert the Bruce, the Ulster Plantation, the Siege of Londonderry, Andrew Jackson, the Hatfields and McCoys, the Civil War, and even Vietnam. Webb makes the case that this lineage of defiant, self-reliant fighters played a pivotal role in America’s military, politics, and cultural ethos.
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While some of Webb’s generalizations are sweeping, his perspective is refreshingly unfiltered. He forces us to reconsider the origins of stereotypes surrounding the “redneck” South, the Confederacy, and working-class white America. Some criticisms are deserved, but many stem from historical and economic realities that get flattened in modern discourse. The more we understand these nuances, the better we can reckon with our past and shape our future.
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One gripe: given how much of this story is tied to geography, why is there no map? I kept wanting to trace the Scots-Irish migration, but instead, I had to rely on Google.
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Weird Reading Gadget I'm Testing
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I’ve tried clip-on book lights, but they always felt like a hassle. With a newborn in the house, keeping the lights low is non-negotiable—for her sleep and my rare, precious naps. So, out of desperation, I picked up this weird-looking around-the-neck reading light.
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Yeah, it looks ridiculous. But it’s a game-changer. Three color modes, six brightness settings, and—best of all—it actually works. I’ll definitely be bringing this on flights, subtly irritating my rowmates as they try (and fail) to sleep through my late-night page-turning.
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40 Thoughts on Turning 40
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Writer Paul Millerd recently shared some reflections on his blog. I love these kinds of posts. Check out some of my favorite tips from the article below:
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A “good job” can still be bad work. It’s easy to confuse a life that makes sense on paper with one that fills your heart and soul.
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Defining success on your own terms will create tension with those around you who don’t value the same things. It is easier to succeed like those around you but more satisfying to make progress against your own secret mission over the long-term.
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I had some theories about parenting and how to raise kids. And then I had a child.
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I’ve never seen a single person become happier by spending more time following politics or the news.
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Reading history gives you more appreciation for the present by helping you see how consistently crazy humans have been at all times in history and how much more comfortable and safer the world has become.
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Writing is one of the most powerful acts in the world. It’s never too late to start. But beware of its power in exposing you to what you truly desire.
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What I'm Watching
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I distinctly remember watching the movie Black Hawk Down when it came out in 2001 because it was by far the LOUDEST fucking movie I'd ever seen. It was two and a half hours of ear-bleeding gunfire, RPG explosions, and yelling.
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What I didn't realize was just how accurate that barrage of artillery was during the real-life battle in Mogadishu.
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This documentary tells the full story of the 160 elite US soldiers who dropped into Mogadishu in October 1993 to capture two top lieutenants of a renegade warlord. They interview Somalians who were there to witness the events leading up to that fatal day and the catastrophe that ensued.
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It's a brutal but incredible three-part series showing war's ugly side.
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What I'm Listening To
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Chase Hughes is a retired US Navy Chief and is the leading military and intelligence behavior expert with 20 years of creating the most advanced behavior skill courses and tactics available worldwide. He is a Harvard-educated neuroscientist, keynote speaker, and the author of two bestselling books, including The Behavior Operations Manual (which is now selling for $177(!) on Amazon).
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This episode was wild. I'm fascinated by people who deeply understand psychological areas of manipulation, power, and non-verbal analysis. Hughes discusses the efforts of cult leaders, car salesmen, and hypnotists to establish trust with total strangers to psychologically alter their behavior with subtle tricks.
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One thing I enjoyed was how Chase determined the "Five Things That Create Gut Feelings in People for Confidence." In other words, how do we identify who the natural leader is in a given environment? Surprisingly, it has nothing to do with speech.
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- Environment
- Time
- Appearance
- Social Skills
- Financial Life
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What makes a great leader is who that person is outside of their leadership role.
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Quote I'm Pondering
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"It’s not what you gather, but what you scatter that tells what kind of life you have lived."—Helen Walton
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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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