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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 10th, 2025 | by Kyle Brennan
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Say Hello to Macy Jean Brennan!
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š Best New Year’s Eve ever. Meet Macy Jean Brennan, our little miracle and newest addition to the family, born on the very last day of the year. Turns out, 2024 ended with a bang—and a baby. š¶š
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Thought of the Week
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"Guilt is a feeling you have when you're acting out of alignment with your values."
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Think about that for a moment. Guilt isn’t just a generic bad feeling—it’s a signal that you’ve veered off the road of who you strive to be.
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Yet time and again, we let guilt—or its uglier cousin, shame—run the show. Guilt says, “I did something wrong.” Shame doubles down: “I am wrong.” But our understanding of guilt is often completely off-base.
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As Dr. Kennedy explains, if we’re truly acting in alignment with our values, it’s not guilt. Guilt only surfaces when we’re out of step with the person we want to be.
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For example, if I screamed at a barista for messing up my coffee order (something I’d never do), I’d feel immense guilt because yelling at people isn’t who I am or want to be.
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On the other hand, if I set a boundary with a coworker—say, no meetings before 10 a.m.—I wouldn’t feel guilty. Because that’s not guilt; it’s clarity. I know I’m most focused and productive between 8 and 10 a.m. Afternoons? Go ahead, book me up. But my mornings? Non-negotiable.
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The problem is, we often confuse guilt with discomfort. When someone doesn’t like our boundaries, we internalize their distress and mislabel it as guilt. It’s like saying, “I see your feelings and I will carry them for you.”
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But let’s be clear: that’s not guilt—it’s codependence with a guilt mask.
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Setting boundaries—especially with the people we love—is uncomfortable, for sure. But it’s also necessary if we want to live a life aligned with our values.
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Boundaries aren’t about controlling others; they’re about defining how we operate.
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The other person doesn’t have to like, agree with, or even comply with your boundary. You’re not asking for permission—you’re declaring a personal policy. That’s it.
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So next time you feel that pang of “guilt,” ask yourself: is this guilt, or is it just discomfort from prioritizing what matters to me?
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What I'm Reading
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This is the third book by Erik Larson I’ve read and it’s undoubtedly his best one, in my opinion. He is a master of turning history into page-turners.
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Some of my favorites by Larson:
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- The Devil in the White City
- The Splendid and the VileThe story centers on William Dodd, a mild-mannered history professor from Chicago with modest political connections and an even more modest ambition: he wanted a quiet government post so he could finish writing his book on the American Civil War. But when Franklin D. Roosevelt couldn’t convince anyone else to take the job, Dodd found himself appointed as the U.S. ambassador to Germany in 1933—right as Hitler was consolidating power. Talk about a career pivot.
Dodd packed up his wife and two grown children and headed to Berlin, where they were greeted by a Germany still licking its wounds from World War I but rapidly succumbing to the feverish nationalism and brutal authoritarianism of the Nazi regime. Initially, like many Americans, Dodd thought Hitler might cool his temper over time. But as he interacted with Nazi officials and observed the escalating violence and propaganda, he soon realized: Hitler and the Nazis were a threat not just to Germany, but to the entire world.
The book’s other central figure is Dodd’s daughter, Martha, whose love life deserves its own historical footnote. Recently separated from her first husband, Martha took full advantage of Berlin’s social whirl. She dated everyone from the head of the Gestapo to a top Soviet spy, and there was even a bizarre Nazi plot to pair her off with Hitler himself. Let’s just say Martha didn’t let ideology get in the way of romance.
What makes In the Garden of Beasts so compelling is Larson’s ability to show us Germany’s rapid descent into madness through the eyes of a family that arrived as outsiders and quickly realized they were witnessing history’s darkest chapter unfold. It’s one thing to read about Nazi Germany in hindsight; it’s another to see it through the bewildered perspective of Americans who initially struggled to comprehend the magnitude of what was happening.
Rating: 4.1 / 5 āļøāļøāļøāļø
My Latest Article
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Back in March 2021, I published a blog post titled Five Realizations That Changed My Life. To my surprise, it became one of my most popular posts. I hadn’t revisited it until last month when my mom handed me a passage she’d printed out.
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Since then, life has been a whirlwind — I got married, started a new job, moved to the suburbs, became an uncle, and weathered plenty of ups and downs. Revisiting that post now, I see how much my perspective has evolved while also realizing how these five realizations have remained core to my worldview.
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I’ve updated the post with fresh insights, reflecting both what’s changed and what’s stayed true. I hope you enjoy this revisited version.
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What I'm Watching
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Anyone who was cast to play such an iconic figure was going to be the subject of major criticism, but Timothee Chalamet absolutely outdid himself in this performance. I was blown away by his portrayal of Dylan and his ability to speak, sing, and play guitar like one of the greats.
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I've never been a huge fan of Bob Dylan (I always equated his style to John C. Reilly's hilarious parody of Dylan in the movie, Walk Hard). However, I've never lacked appreciation for his contributions to music and songwriting - especially songs made popular by other artists (Jimi Hendrix's All Along the Watchtower, Old Crow Medicine Show's Wagon Wheel, and Adele's Make You Feel My Love). But after watching this film, I fell into the Dylan rabbit hole and have grown a much bigger fan of his work.
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I'm honestly excited to watch this movie again sometime soon.
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Gurwinder Bhogal is one of my favorite writers/thinkers on the internet. He has a special knack for simplifying concepts into bite-sized nuggets of wisdom. This year, he compiled 25 mental models to kickstart the new year.
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A couple of gems from this post that I'll be chewing on:
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- Enshittification: Online services start out serving users. When they have enough users, they switch to serving advertisers/shareholders, at the expense of users. For instance, Google Search initially showed you what you searched for, but now largely shows you what it wants you to see.
- Dawkins’ Law of the Conservation of Difficulty: The easier an academic field, the more it will try to preserve its difficulty by using complex jargon. Physicists use simple terms if possible, while postmodern theorists try to complexify their discipline
- Explanatory Inversion: Questions rest on unexamined assumptions, so always try flipping them. For instance, don’t just ask why there is poverty, ask why there is prosperity. This helps you realize poverty is the norm and the lack of it is the thing that needs to be explained.
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Feel-Good Television I Recommend
My wife and I have wildly incompatible tastes in entertainment. I’m into action-packed movies, gritty TV dramas, WWII documentaries, and stand-up comedy. Lauren, on the other hand, prefers anything that avoids violence, sadness, or death—which, if you’re keeping track, eliminates about 99% of the good stuff.
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Instead of pouting because I can’t watch Yellowstone, The Penguin, or Better Call Saul, I read (a lot...). But when I’m not reading, we compromise with what we call “feel-good” TV.
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Make no mistake: finding good options is like searching for a needle in a Hallmark haystack. We’ve endured our fair share of painfully mediocre shows, but a few gems managed to slip through.
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Here’s a list of the best “feel-good” movies, shows, and documentaries Lauren and I have agreed on—proof that miracles do exist.
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- Ted Lasso
- Schitt's Creek
- Parks & Recreation
- Shrinking
- New Girl
- The Good Place
- Brooklyn Nine-Nine
- A.P. Bio
- Hunt for the Wilderpeople
- The Boy Who Harnessed the Wind
- Chef
- The Martian
- The Holiday
- Nacho Libre
- School of Rock
- Scott Pilgrim vs. The World
- Sgt. Bilko
- Groundhog Day
- Inside Out
- Pitch Perfect
- Dealt
- My Octopus Teacher
- Welcome to Wrexham
- Stutz
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Quote I'm Pondering
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"If a plant cannot live according to its nature, it dies; and so a man."
-- Henry David Thoreau
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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 33rdĀ Birthday
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Thirty-three was a big one. Mostly because I became a dad. Our daughter was born on New Yearās Eveāāāa fitting arrival for a kid destined to reset everything. Itās been a beautiful, if slightly sleep-deprived blur ever since. Iāve only been āDadā for less than ten months, but if Iām being honest, Iāve 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 ā or a better life. In the age of AI and tweet-sized wisdom, weāve confusedĀ informationĀ withĀ transformation. But thereās a massive difference between knowing what a book says and beingĀ changedĀ by it. The Delusion of Instant Learning In a recentĀ 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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Thereās no difference between a pessimist who says, āOh, itās hopeless, so donāt bother doing anything,ā and an optimist who says, āDonāt bother doing anything, itās going to turn out fine anyway.ā Either way, nothing happens.ā ā āYvon Chouinard, Founder of Patagonia I donāt read much fiction, but Iāve always been hooked on Lee ChildāsĀ Jack Reacher. Heās not your typical …
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