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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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March 28th, 2025 | by Kyle Brennan
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Thought of the Week
Some People Are Lessons in What Not to Be
Sometimes life sends us teachers disguised as cautionary tales.
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We cross paths with people who seem stuck—repeating the same patterns, clinging to outdated beliefs, and resisting change like it’s an existential threat.
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At first, it’s frustrating. You might wonder, How can they not see it? You might even try to help, only to feel like anything you say to them goes in one ear and out the other.
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But eventually, you realize some people were not put here to evolve. They are here to remind you what it looks like if you don't
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These people are mirrors, showing you what happens when growth and self-reflection is avoided. They serve as powerful, if uncomfortable, lessons in what not to become.
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Rather than getting stuck in judgment or resentment, use them as fuel. Let their lack of change light a fire under your own evolution. See their story as a warning—a vivid example of how refusing to adapt can turn potential into inertia.
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Sometimes the best teachers are the ones who never move forward, because they remind you to keep moving.
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What I'm Reading
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Full transparency, I was given this book by a publicist in exchange for a review on my Instagram page—an offer I get every once in a while but tend to turn down since I don't want reading to become a chore. I truly only want to read books I know I'm going to enjoy.
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But in this case, the publicist shared that this was a book written for personal finance beginners and takes only an hour to read. I'm about halfway through and so far it provides some interesting tips about how to understand individual stock trends by analyzing their historical performance in a few easily identifiable steps.
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Full description from Amazon:
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Stikky Stock Charts uses a simple, pattern-based learning method to bring a valuable skill to anyone with a ruler and an hour to spare. We took the latest research into patterns and spent hundreds of hours with readers testing and simplifying it to be sure it will work for you. Includes a comprehensive Next Steps section with guides to the eight steps to begin trading, four classes of broker, major investment types, software, stock data, free sources of charts, and more.
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Article I'm Reading
I've shared before that Gurwinder Bhogal is one of my favorite writers on the Internet (follow him on X). He writes about topics in a way that helps me explore the outer edges of my own curiosity.
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This article in particular was really interesting. He introduces us to another fascinating writer & thinker, Freya India—a journalist focused on female mental health and modern culture, and someone whom I only recently started paying attention to. I now subscribe to her Substack.
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The article is a fascinating month-long letter exchange between Gurwinder and Freya, exploring how we can maintain our agency and connection in an age of increasing automation and alienation.
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Some of my favorite excerpts from the exchange:
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- To me, the greater danger of AI is not that machines will think for themselves, but that humans will cease to.
- My main concern isn’t so much losing human creativity or everyone having AI girlfriends, but that someday we won’t trust ourselves at all. I see a future where young people won’t trust any instinct they have without checking with ChatGPT first. Where they will ask AI to solve relationship problems, to calculate who is right in an argument, to make decisions for them instead of going with their gut.
- I therefore see AI as a personality amplifier; it will give more agency to those who already have it, and take more from those who already lack it.
- For me, the best brain-gym is writing—it forces you to shut out distractions and listen to your thoughts
The Ultimate Book List
The Ultimate Book List is a directory of books recommended by famous personalities, celebrities, and experts. I like that it includes source links to interviews and articles where these books were mentioned. If you’re just browsing, you can filter all the listed books by "most recommended."
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It's crazy to think there are like 3-4 books that I can attribute 99% of my life to. Things would be so unimaginably different without them.
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If I were in charge I would make every young adult read the following books:
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- Endurance—Alfred Lansing
- Atomic Habits—James Clear
- The Psychology of Money—Morgan Housel
- Man's Search for Meaning—Viktor Frankl
- Influence—Robert Cialdini
- The Lessons of History—Will & Ariel Durant
- The War of Art—Steven Pressfield
- Can't Hurt Me—David Goggins
- The Untethered Soul—Michael Singer
- Four Thousand Weeks—Oliver Burkeman
- Tools of Titans—Tim Ferriss
- The Almanack of Naval Ravikant—Eric Jorgenson
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Underrated Career Advice I'm Following
Be the person your boss brags about in every meeting
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Next week, I return to my full-time job after three months of generous Paternity Leave from my company. I'm excited to return to work with a new perspective on how best to thrive without the icky feelings of self-promotion and back-patting.
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The idea is to recognize that you don’t work for your company’s CEO or the head of your group. You work for the person who sits directly above you in rank.
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The primary goal is to make your boss look good. How can you make their life easier? Be proactive in navigating inefficiencies. Come to them with solutions, not problems. Frame your achievements in a way that highlights their leadership and vision.
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It's not about blind obedience. It's about understanding human nature and power dynamics and navigating them effectively, rather than being a pushover.
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Make your boss look good, and the promotions and pay raises will naturally follow.
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What I'm Listening To
How to Increase Your Speed, Mobility & Longevity with Plyometrics & Sprinting
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95% of adults over the age of 30 will never sprint again for the rest of their life.
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Yet sprinting is one of the most fundamental human skills—and a secret weapon for staying fit well into retirement.
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So how do we keep the ability to sprint on demand, despite the joint pain, stiffness, and general loss of athleticism that aging hands us?
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Simple: normalize skipping.
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Yes, skipping—the thing you probably haven’t done since grade school. Turns out, it’s the ultimate cheat code for staying quick on your feet.
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Stuart McMillan is a renowned track and field coach who has trained dozens of Olympic medalists, professional athletes, and team coaches across a diverse range of sports.
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In this episode, McMillan discusses using plyometric work to improve mobility, strength, posture, and overall health. He also explains why skipping isn't just for kids—it's an incredible effective tool for adults looking to move better, build coordination, and prepare their bodies for sprinting. It taxes the system in a why that's surprisingly close to sprinting—without the injury risk. It's low-impact, highly adaptable, and a smart way to reintroduce speed safely.
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If you're not a fitness nerd like me, the 3-hour podcast might be a bit too "inside-baseball." But, if you want to incorporate more skipping and sprinting into your fitness routine, I highly recommend the 25-minute YouTube instructional with Stu McMillan and Andrew Huberman on a track in Malibu.
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On this topic, no amount of social media fitness inspiration has impacted me more than this photo:
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Exercise is the fountain of youth.
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Quote I'm Pondering
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"Travel is not reward for working, it's education for living."
—Anthony Bourdain
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Keith Welcomes Lucy Rose Sullivan!
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At 12:04am this morning, my podcast co-host and producer Keith, and his wife Lizzie, welcomed their second daughter, Lucy Rose Sullivan to their growing family.
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We now have three daughters under the age of three between the two of us, so needless to say, it may be a while until we get a chance to sit down for our next podcast episode.
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We hope you understand and thank you for being patient and supporting the pod!
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Observe and Rapport is a blog, Instagram, and podcast channel that discusses wisdom, perspective, and lifestyle habits gained from books and other historical forms of media.
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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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