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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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November 9th, 2024 | by Kyle Brennan
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Thought of the Week
What Does Winning Really Mean?
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Some say competition is toxic, that it brings out the worst in us. They may point to activities like surfing, where the goal seems to be harmony, not victory.
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Fair enough. But aren't surfers competing - if not against others, then against the waves themselves? If all they wanted was “flow,” surfers could ride any medium-sized wave.
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But they don't. They wait. They scan the horizon for the big one—the wave that demands everything they’ve got. Why?
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Because competition isn’t about avoiding challenges. It’s about embracing them. It's those very obstacles - the size and churning power of the wave, which draw from the surfer his greatest effort. It is only against the big waves that he is required to use all his skill, all his courage and concentration to overcome. Only then can he realize the true limits of his capacities.
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The same is true in any competition. The 2007 New York Giants didn’t just win the Super Bowl—they beat the undefeated Patriots (!), one of the greatest teams in NFL history. That’s what made it legendary.
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In whatever challenge you're faced with, your opponent’s job is to make life as hard as possible for you, just as it’s your job to do the same for them.
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The "opponent" in this sense doesn't have to be a person - it could be a deadline, an expectation, or a skill you've yet to master. Without that tension, without those obstacles, there’s no glory—only mediocrity.
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Winning isn’t about crushing others. It’s about challenging yourself to rise to the occasion.
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It’s the surfer staring down the biggest wave, the team facing the undefeated dynasty, and the moment you realize that the struggle itself is what makes the victory worth it.
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What I'm Reading
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I don't even play tennis, but I picked up this book because it's been recommended by Tim Ferriss, Bill Gates, Pete Carroll, and Steve Kerr as a manual, not merely about tennis, but about getting out of your own way.
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The Inner Game of Tennis is an exploration of the psychological battles we face within ourselves. How to achieve the state of "relaxed concentration" in any domain. If you've played any sports or games you know what it feels like to be In The Zone - where everything flows effortlessly. This state is familiar to most, but what's preventing us from being in the zone every game?
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Gallwey presents the theory of two selves: Self 1 is the thinking brain, always analyzing and judging - essentially our inner dialogue. Self 2 is your "feeling and doing" brain. The book details all of the ways Self 2 can master almost anything in a short amount of time, if only we don't allow Self 1 to interfere.
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Only about a third of the book is specifically tennis-focused, but the rest details mindfulness techniques and instructs the reader on how to allow your body and mind to learn without judgment or commentary. To shut the internal voice and just focus on the task at hand.
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Here are some of my favorite strategies that I'll be implementing:
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- Images are better than words, showing is better than telling
- “Forget should’s and experience is."
- It's more effective to visualize the result you want, and Self 2 will figure out the how all by itself.
- One of the best ways to replace Self 1's habits is through focus. For example, focus your attention on the seams of the ball as it spins or the sound the ball is making.
- Create a mind shift simply by saying, "But if I could..." and doing that thing.
For example: "If I could putt well, it would look like this."
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Even if you don't play tennis or even sports in general, this book and its principles of letting go of mistakes and moving forward with knowledge and experience but not self-judgment are wonderfully helpful in this grand game we call life. I hope you read this book too, because it's a game-changer.
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My Latest Article
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Sometimes, you make a decision that even you can’t explain — but in 2022, I found myself doing just that.
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When COVID-19 hit, I realized quickly that I didn’t have a single skill the world needed in a crisis. I didn’t know CPR, couldn’t fix a flat, and had no idea what I’d do in a real emergency. I wanted to change that — to prove to myself that when things went sideways, I could be someone worth calling on.
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An unexpected thought occurred to me, “What if I became a firefighter?”
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Even though I didn’t know the first thing about being a volunteer firefighter, I knew it was the perfect combination of meaning, commitment, service, skill, and purpose that I was looking for.
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X Thread Worth Bookmarking
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Elon Musk went all in on Donald Trump.
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When the Philadelphia Eagles were on 4th & goal with one minute left in the half vs. the Patriots in the 2018 Super Bowl, they ignored the conventional wisdom to kick a field goal.
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But not only did they go for it, they ran a trick play - a flea fleaker - one of the riskiest plays in football.
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In a high-stakes moment, they went all in took the maximum risk, and pulled it off.
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On November 5th, @ShaanVP explained how Elon Musk pulled off his Philly Special.
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What I'm Watching
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The other day I was reading on the couch when my wife asked me if she could watch a show. "Sure," I said. I didn't mind and wasn't expecting her to turn on anything I'd be particularly interested in. But then my eyes gradually turned their attention away from my book and towards the screen as I began hearing the tale of Martha Stewart.
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I was somewhat familiar with her career and global homemaking brand, but I had no idea about her come-up story. First, she went from being a model to a stock broker, then she launched her own catering business that showcased her knack for cooking, decorating, and lifestyle curation. Gradually, her unique approach to homemaking resonated with audiences, leading her to publish successful cookbooks and eventually launch Martha Stewart Living, a media empire that spanned magazines, TV shows, and products.
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Martha followed her vision with meticulous intensity until she turned herself into a household name and lifestyle icon.
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Article I'm Reading
"[Newspapers] must be accurate, and [they] must be believed to be accurate."
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Take Jeff Bezos' memo with a grain of salt (he later came out of the Twitter shadows to congratulate Trump on his victory), but everything he says in this article is 100% true.
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I'll state the obvious for the thousandth time, but it's clear as day: the American public no longer trusts the mainstream media. Rather than provide objective facts and information, they've become moralizers. "Agree with us, or be ostracized."
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If you haven't already, subscribe to The Free Press. In my opinion, the best bastion of cold hard journalism we have going today.
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Quote I'm Pondering
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"I finally found my rhythm when I realized that even the steps backward were part of the dance."
- Melody Godfred
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When my brother Tommy told me he was doing another crazy mountain race, I knew we had to have him on the podcast. If you're not familiar (as I'm sure you aren't), 29029 Everesting is an endurance event that takes place at various mountains in North America. You have 36 hours to climb 29,029 feet - the equivalent height of Mt. Everest. Hike up the mountain, take the gondola down, and repeat.
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As a spectator, I can attest to just how brutal of an event this is.
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In this episode, expect to learn about Tom's recent completion and overall experience participating in the event 29029 Everesting, the journey that led him to decide to take on the challenge, the benefits of willingly doing hard things, and how a bad experience can lead to the ultimate alleviation of lingering pain.
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My Amazon Favorites Bookstore
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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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