Weekend Briefing No. 575

Kyle Westaway

Feb 15, 2025

Welcome to the weekend.

Prime Numbers

162.3 — Meta allegedly downloaded 162.3 terabytes of books from shadow libraries and LibGen for AI training, with internal emails showing employee discomfort about using corporate resources for torrenting copyrighted material.

41 — A survey revealed only 41% of people talk to their dining companions during meals, while screens dominate dinner time with 63% watching TV and 28% checking phones, highlighting a shift in traditional dining social norms.

20 — Sales at Chili's surged 20% year-over-year while the broader casual dining sector fell 3.8%, driven largely by two menu items: a $10.99 value meal and the Triple Dipper appetizer combo, which accounted for 19% and 15% of total sales respectively.

Killing Bad Strategy

Most people believe strategy is about having a perfect plan, but the art of achieving ambitious goals actually lies in the delicate dance between our soaring aspirations and our earthbound limitations. Drawing from 2,500 years of history, the wisdom of great strategists reveals that success comes not from rigid planning but from the fox-like ability to adapt while maintaining unwavering focus on core objectives — a skill exemplified by leaders from Augustus to Lincoln who accomplished seemingly impossible feats. The most dangerous trap in strategic thinking isn't aiming too high or too low, but rather clinging to a failing strategy out of pride or sunk costs, as demonstrated by Pericles who triggered a devastating war by refusing to abandon a flawed decree that had become a matter of pride rather than pragmatism. The key to masterful strategy lies not just in crafting brilliant plans but in having the wisdom and courage to kill bad strategies before they kill you — whether in business, politics or personal life, this requires embracing the paradox of holding both ambitious dreams and practical constraints in mind simultaneously, while remaining flexible enough to seize unexpected opportunities along the way. Rob Henderson (11 minutes)

Asking the Right Questions

In a world where artificial intelligence can instantly provide answers, the true competitive advantage lies in knowing which questions to ask. While most leaders understand that interrogative skills matter, research reveals five distinct types of questions that can revolutionize strategic decision-making: investigative questions that dig deep into what's known, speculative questions that explore what's possible, productive questions that determine what's needed, interpretive questions that make sense of findings, and subjective questions that uncover emotional undercurrents. The art of leadership increasingly depends not on having all the answers but on asking these different types of questions at the right moment, as illustrated by Nvidia CEO Jensen Huang's evolution to spending entire days primarily asking questions rather than providing solutions. Most crucially, the questions that derail organizations are often the ones left unasked — those that don't naturally arise from our expertise, habits or comfort zones. Harvard Business Review (23 minutes)

How Many years Will You Live?

For those who optimize everything—your healthspan is no exception. Take the Longevity Quiz from Super Age, a new media brand built to deliver cutting-edge insights on longevity, vitality, and peak performance. Discover how your lifestyle, mindset, and daily habits stack up against the latest research, and get personalized strategies to extend your strongest years. Plus, we’ll send you our flagship newsletter, The Mindset, which dives into everything from sleep to sex, fitness to bodywork, nutrition and breakthroughs in longevity science. Longevity isn’t about guessing—it’s about strategy. Ready to see where you stand? Take the Super Age Longevity Quiz today. Super Age (Sponsored)

Suffering to Strength

Freedom resides not in our circumstances but in our response to them — a truth powerfully illustrated through the extraordinary prison letters of Václav Havel to his wife Olga. Despite facing a sadistic warden, harsh labor and strict censorship of his weekly four-page letters, the future Czech president transformed his imprisonment into an opportunity for profound self-refinement rather than surrendering to bitterness. When offered early release in exchange for renouncing his beliefs, Havel chose to maintain his integrity even as his health deteriorated, demonstrating how constraints can become a catalyst for creativity and character. His journey from prisoner to president illuminates an eternal truth: while we cannot control what happens to us, our capacity to find meaning in suffering and emerge stronger may be the ultimate measure of human freedom. Whether faced with physical imprisonment or the prisons of our own making, we always retain the power to choose growth over grudges, openness over isolation and love over hate. The Marginalia (7 minutes)

Thoughts Lead to Actions

What fills your mental bandwidth shapes your entire life trajectory, yet we rarely choose these thought patterns deliberately. Much like checking your phone's app usage reveals surprising patterns, our minds can become dominated by unproductive obsessions — from political arguments to past relationships — that hijack hours of mental energy and steer us away from our most meaningful goals. Simple environmental cues, like a gas price sign triggering a spiral of economic anxiety, can spawn self-sustaining "weather systems" of thought that color entire days. The good news is that we can intentionally redirect our mental focus by curating our inputs, whether that means switching from news feeds to creative projects or replacing social media scrolling with skill development. Whether your mind dwells on building a business or rehashing old arguments, these mental preoccupations act as invisible architects of your future, shaping everything from your daily habits to your life's ultimate direction. Raptitude (6 minutes)

The Mental Gym

Imagine if you could upgrade your mental operating system as easily as you build physical muscle. While most of us understand the importance of physical exercise, we often overlook the equally crucial need to systematically train our minds through four foundational pillars: curiosity, creativity, mindfulness and rest. 1) Curiosity drives us to learn and teach others, strengthening neural pathways through active engagement with new information and ideas. 2) Creative activities like drawing or music-making enhance emotional resilience and well-being without requiring professional training. 3) Mindfulness, achieved through simple practices like deep breathing or expressive writing, creates essential space for processing emotions in our hectic lives. 4) Finally, quality sleep and strategic napping aren't lazy indulgences but crucial periods when our brains consolidate learning and recharge for optimal performance, completing this powerful framework for cognitive enhancement. Ness Labs (6 minutes)

A Life Worth Living

What if our obsession with living longer is actually preventing us from living better? Despite the booming $37 billion longevity industry filled with plasma swaps and vampire facials, science reveals that our lifespan is largely dictated by factors outside of our control — from genetics to socioeconomic conditions. While healthy habits like consistent sleep and moderate eating can add approximately five years to our lives, the obsessive pursuit of eternal youth often robs us of precious moments that make life worth living — from sunlit conversations with friends to spontaneous adventures that create lasting memories. The reality of death's unpredictability is illustrated through stories of health-conscious individuals who passed away unexpectedly, reminding us that aging itself is a privilege denied to many. Outside (8 minutes)

Should We Work Together?

Hi! I’m Kyle. This newsletter is my passion project. When I’m not writing, I run a law firm that helps startups move fast without breaking things. Most founders want a trusted legal partner, but they hate surprise legal bills. At Westaway, we take care of your startup’s legal needs for a flat, monthly fee so you can control your costs and focus on scaling your business. If you’re interested, let’s jump on a call to see if you’re a good fit for the firm. Click here to schedule a one-on-one call with me.