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Welcome back to A Little Wiser. We hope everyone is looking forward to a great weekend. Thanks to Cervante from the Money Tips Money Hacks newsletter for writing today’s guest lesson. Today’s wisdom explores:

  • What Two Young Winter Olympians Can Teach Us About Winning

  • Decoding the Oscars' Unpredictable Ballot

  • Guest lesson by the Money Tips Money Hacks Newsletter

Grab your coffee and let’s dive in.

PSYCHOLOGY
🎿 What Two Young Winter Olympians Can Teach Us About Winning

Two Olympic champions in their early twenties have articulated a philosophy of performance that most elite athletes spend decades failing to understand. Eileen Gu, the 22-year-old freestyle skiing sensation, has won multiple Olympic gold medals across the 2022 Beijing and 2026 Milan-Cortina Games and is the most decorated female freeskier in history. Beyond the slopes, she's a signed supermodel walking runways for Louis Vuitton and a Stanford graduate who studied quantum mechanics while competing internationally. Alysa Liu became the youngest U.S. figure skating national champion at 13, retired at 16 because the sport had stopped being fun, and returned two years later to win Olympic gold with a completely transformed approach. What makes them remarkable is that they both have rejected the traditional narrative about what it takes to win focusing instead on neuroplasticity, self-compassion, and the radical idea that having fun and maintaining balance might be the ultimate competitive advantage.

Eileen Gu approaches competition like a neuroscientist studying her own brain. In interviews, she's explained that "you can control what you think, and therefore you can control who you are," a concept she backs up with an understanding of neuroplasticity, the brain's ability to rewire itself through deliberate practice and thought patterns. She journals obsessively, breaking down her thought processes with what she calls "a very analytical lens," constantly asking herself, "How can I be better? How can I approach my own brain?" When journalists asked if her two silver medals at the 2026 Olympics were "two golds lost," she laughed and called it a "ridiculous perspective," reframing the question entirely by highlighting how losing is never a failure. She promotes what she calls a next play mentality, borrowed from basketball, where dwelling on what could have been is a waste of energy better spent on the next attempt. She credits her success to balance, never sacrificing her education for skiing, which she says helped her conceptualize tricks in ways pure athletes couldn't. Her philosophy is almost scientific: "Learning to learn is the most important thing an individual can do in life," and she treats athletic performance as applied problem-solving while always focusing on the positives.

Alysa Liu's path to gold began with quitting. She won her first U.S. national title at 13, competed in the 2022 Olympics at 16, and then walked away because she was tired of not having fun, tired of losing her identity to the relentless pressure of elite sport. For two years, she stepped away entirely. When she returned, it was with a singular goal: to have as much fun on the ice as possible. Going into the women's figure skating final at the 2026 Olympics, she was in third place. Her response to the pressure was remarkable: "Even if I mess up and fall, that's totally okay too. I'm fine with any outcome, as long as I'm out there." She won gold, and one of the first things she said afterward was, "That was so much fun!" In a 60 Minutes feature, she said something that sounds almost contradictory: "I love struggling actually. It makes me feel alive." She thrives on the "constant pounding in pursuit of perfection," repeating "one more" to herself after falls during practice, not because she's punishing herself but because the challenge itself is what keeps her engaged. In Cosmopolitan, she articulated the shift that saved her career: "These scores and placements, they don't affect your art. Your art is still your art. This time, I'm really passionate about it." The lesson from both Alysa and Eileen is that they have figured out how to protect what made them fall in love with their craft in the first place. Gu treats her mind like a tool she can sharpen through deliberate practice and balance. Liu learned that walking away when joy disappears isn't quitting and that coming back on your own terms is what separates sustainable excellence from burnout. These two champions are thriving with careers built on curiosity, self-awareness, and the understanding that if you're not having fun, you won't last long enough to become great.

Below - Eileen’s press conference highlights her impressive mindset as she talks about factors behind her success.

FILM
🎬 Decoding the Oscars' Unpredictable Ballot

Most people assume the Oscars work like any other election: whoever gets the most votes wins. That's true for 23 of the 24 categories, but Best Picture uses a system so convoluted that even Academy members sometimes admit they don't fully understand it. It's called preferential voting, or ranked-choice voting, and it was designed to ensure that the winner has broad support rather than just passionate fans. Here's how it works: all 10,500 voting members rank the Best Picture nominees from one to ten in order of preference. If a film gets more than 50% of first-place votes, it wins immediately, but that almost never happens. So the film with the fewest first-place votes is eliminated, and anyone who ranked that film first has their ballot redistributed to their second choice. This process repeats, round after round, until one film crosses the 50% threshold. The result is that a movie with the most first-place votes can still lose if it's polarizing, while a film that nobody hates but everyone kind of likes can win even if it wasn't anyone's favorite. It's why critics argue "Crash" beat "Brokeback Mountain" in 2006 and why campaign strategists tell their clients to be everyone's second choice rather than half the room's obsession and the other half's enemy.

The system creates bizarre strategic incentives and occasionally produces results that feel like they came from a parallel universe. In 2017, PricewaterhouseCoopers, the accounting firm that tabulates the votes, handed Warren Beatty and Faye Dunaway the wrong envelope during the Best Picture announcement, resulting in "La La Land" being declared the winner for a full two minutes before the mistake was corrected and "Moonlight" was revealed as the actual victor. Only two PwC partners know the results beforehand, and they stand in opposite wings of the theater clutching identical briefcases full of sealed envelopes, a security protocol that seems designed for a nuclear launch rather than an awards show. The preferential ballot also explains why campaigns matter so much, studios spend millions flying Academy members to private screenings, hosting Q&As with directors, and buying full-page ads in trade publications, all to ensure their film shows up somewhere on voters' ranked ballots. Being ranked fifth on 8,000 ballots is more valuable than being ranked first on 2,000 and completely ignored by everyone else.

This year's Best Actor race is the most wide-open in recent memory, which almost never happens. Usually, the winner is decided weeks before the ceremony because they've already swept the Golden Globes, the BAFTAs, and the Screen Actors Guild award, the three precursors that historically predict the Oscar with startling accuracy. But in 2026, different actors have won every major award. Timothée Chalamet was the frontrunner for "Marty Supreme" after dominating early in the season, but then he lost the BAFTA to Robert Aramayo for "I Swear," a film that wasn't even Oscar-eligible, suggesting BAFTA voters were sending a message or simply operating on a completely different wavelength. The five Best Actor nominees are Timothée Chalamet, Leonardo DiCaprio, Ethan Hawke, Michael B. Jordan, and Wagner Moura. DiCaprio is in "One Battle After Another," which has 13 nominations and is the presumed Best Picture favorite, but he's already won an Oscar and the performance isn't considered transformative enough to justify a second. Ethan Hawke is getting his first lead actor nomination after decades of grinding, playing legendary musician Lorenz Hart in "Blue Moon," but the film only got two nominations total, signaling weak support. Michael B. Jordan is playing twin brothers in "Sinners," the year's most-nominated film. Wagner Moura wasn't even nominated at BAFTA or SAG but is in a Best Picture nominee and has been running a strong campaign. For the first time in years, there is no clear favorite, which means the envelope opening on Oscar night might actually contain genuine suspense instead of a foregone conclusion.

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FEATURE
💻 Guest lesson by the Money Tips Money Hacks Newsletter

I used to think money was the goal. If I could just earn more, save more, spend smarter, then life would fall into place. On the outside, I was doing everything “right.” But underneath the structure, something felt off. I was managing money without understanding what it was really for. When I finally slowed down, I saw that my spending was already telling a story. Not just what I was buying, but why. I could see where I was coping, where I was connecting, where I was investing in an identity I hadn’t fully examined. The numbers weren’t just data. They were signals. They forced better questions: What do I keep choosing? What do I avoid? What actually stays meaningful after the transaction fades? Money stopped being something I chased and started becoming something I listened to. And in that shift, I realized financial practices aren’t just about optimization. They’re about awareness. Once I understood that, everything became clearer.

The turning point wasn’t dramatic. It was subtle. I added a category to my budget called “joy.” Not impulse. Not distraction. Joy. That small line item required honesty. What actually makes me feel present? What brings energy instead of escape? Around the same time, I stopped upgrading things out of habit. Nicer shoes. Better phone. Sleeker furniture. The emotional return kept shrinking. I had to ask a harder question: What need am I really trying to meet? Approval? Progress? Security? Once I identified the real need, I often found better ways to meet it, ways that didn’t leave me with buyer’s remorse or emotional debt. Then came the question that changed everything: What does enough look like? Defining enough quieted the constant chase. It gave me permission to build instead of prove. Alignment replaced accumulation. And peace replaced pressure.

Eventually, I began asking a different question before spending: What would the version of me five years from now be grateful I did today? That one lens slowed impulse and elevated purpose. Urgency stopped making decisions for me. Clarity did. I also reversed my process. Instead of shrinking dreams to fit my paycheck, I dreamed first. What do I actually want my days to feel like? Then I brought the math in. Money became a tool to engineer meaning, not a boundary that confined it. Weekly check-ins stopped being about discipline and started becoming about direction. Five minutes. Honest reflection. Course correction. Money is not just about maintenance. It’s about expression. It’s about casting quiet votes for the life you’re building. When spending reflects values instead of reactions, you stop living on autopilot. You start living on purpose. What you want from life is already inside you. Sometimes you just need to listen to what your money has been saying all along.

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Until next time... A Little Wiser Team

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