Weekend Briefing No. 561
Be Water, My Friend -- On Nostalgia -- Gardening and Parenting
Welcome to the weekend.
I know some of you might be expecting election commentary, but here's the thing. This newsletter is designed to be your Saturday morning breather — a chance to step away from the week's chaotic headlines and sink into something more meaningful while you sip your coffee. We're here to explore ideas that inspire, challenge and help you make a positive mark on the world.
That said, if you're seeking thoughtful political coverage, I can't recommend my friend Isaac Saul's Tangle newsletter enough. It's become my go-to source for its balanced reporting — skillfully presenting both left and right perspectives with credibility.
Lastly, here’s my November playlist, which features Bon Iver, Zach Bryan, Taylor Swift, U2, Noah Kahan, Hozier and others.
Prime Numbers
500 — Remote-controlled aircraft called “first-person-view drones” have transformed warfare in Ukraine by offering a lethal combination of low cost ($500), significant payload (up to 9 pounds of explosives) and mass producibility (thousands per month), making them one of the conflict's most impactful weapons.
500 — Virginia and North Carolina are upgrading their rail infrastructure through major investments, including Virginia's purchase of 500 miles of rail rights, platform improvements, and a $2.3 billion project to double tracks between D.C. and Virginia — enabling 13 daily round trips to Richmond and alleviating a critical bottleneck in the Eastern rail corridor.
14.5 — Americans returned $743 billion in merchandise last year — 14.5% of all retail purchases. My mom and sisters are definitely skewing that national average upward.
Be Water, My Friend
Water, as Bruce Lee famously observed, offers the ultimate blueprint for thriving in an unpredictable world. It adapts instantly to any container, flows around obstacles, and can be both gentle stream and unstoppable force. This seemingly simple metaphor reveals a profound truth about personal growth: true power comes not from rigid resistance but from complete adaptability. By cultivating a "liquid mind" that remains flexible yet purposeful, we can navigate life's challenges with less effort and greater impact. Much like the Stoic philosophers who taught acceptance of what we cannot control, Lee's water principle shows us that mastery comes from flowing with circumstances while maintaining our essential nature — never fighting against reality but moving through it with purpose and wisdom. Postantly Weekly (4 minutes)
On Nostalgia
Memory plays a seductive trick when reflecting on bygone days — stripping away the gut-churning uncertainty of each moment and replacing it with the calm certainty of knowing how everything turned out. From personal relationships to financial markets, we consistently romanticize past eras once we know their happy endings, forgetting the sleepless nights, market crashes and existential fears that dominated those times. Whether it's the idyllic 1950s with their lurking nuclear threat or the "easy" investment opportunities of 2009's economic collapse, this rose-tinted revisionism masks a powerful truth: the past wasn't as golden as we remember, the present isn't as dire as we fear and the future likely holds more promise than our anxious minds permit us to imagine. Collab Fund (4 minutes)
Gardening and Parenting
Modern parenting has morphed from a natural, nurturing relationship into an anxiety-ridden pursuit of perfection, where parents obsess over crafting the "ideal" child as meticulously as a carpenter shapes wood. Yet children, like plants in a garden, aren't meant to be precision-engineered. They require space to grow wild, to adapt to their environment and sometimes to flourish in unexpected ways. The solution to our parenting crisis lies not in more intensive oversight but in creating fertile environments where children can naturally develop, much as gardeners provide the conditions for plants to grow in their own unique ways. The path to happier families may lie in doing less rather than more, trusting children with real responsibility while maintaining a loving, stable presence. Play Makes Us Human (4 minutes)
Autonomous 18-Wheelers
In an era where artificial intelligence seems perpetually five years away, three pioneering companies are mere months from deploying fully autonomous 40-ton semi trucks on American highways. These driverless behemoths, armed with redundant systems and lidar sensors that can see through "dense fog" up to 500 meters ahead, are already quietly hauling cargo on private roads and predetermined routes across Texas. While safety remains paramount — requiring dual computers, backup systems and years of testing — the potential to prevent thousands of annual trucking fatalities makes this technological leap seem not just inevitable but essential. The race between Aurora, Kodiak and Gatik represents distinct approaches to the challenge, from Aurora's deeply integrated systems and massive funding to Kodiak's scrappy modular design and Gatik's cautious focus on shorter, meticulously planned routes. Ars Technica (11 minutes)
Convergent and Divergent Thinking
Like seasoned mountaineers planning an ascent, successful problem-solvers know that reaching the summit requires both exploration and precision. Divergent thinking mirrors the initial route planning phase, where climbers survey every possible path up the mountain, considering unexpected traverses and creative approaches that others might have missed. Convergent thinking functions like the actual ascent, where climbers must methodically analyze each step, using clear criteria to select the safest and most efficient path through challenging terrain. The most effective problem-solvers, like experienced mountaineers, know when to switch between these approaches — first exploring all possibilities, then committing to and executing the optimal route with careful precision. Sunsama (7 minutes)
Read More Books
While the average American spends just 16 minutes reading daily, successful leaders like Warren Buffett dedicate up to 80% of their working day to reading and thinking — suggesting that "too busy" is merely an excuse, not a reality. Reading doesn't just improve memory and focus; it creates a mental scaffolding that helps connect seemingly unrelated ideas, much like completing a complex puzzle one piece at a time. The key to maximizing reading's benefits lies not in consuming vast quantities of random content, but in developing a "white hot core" of knowledge by diving deep into specific topics that genuinely interest you, allowing your understanding to expand organically from that foundation. Not Boring (6 minutes)
Own Your Calendar
Contrary to popular belief, mastering productivity isn't about cramming more tasks into your day or obsessively tracking output metrics — it's about deliberately allocating time blocks that align with your core values. By focusing on controllable inputs (time and attention) rather than unpredictable outputs (completed tasks), individuals can create a sustainable framework for success through a practice called timeboxing. The key is identifying your fundamental values across personal, professional and relationship domains, then translating those values into specific time commitments in your calendar. Most importantly, this value-driven approach to time management requires unwavering commitment to your scheduled blocks, regardless of external pressures or distractions, ensuring you consistently invest in what truly matters. Nir and Far (5 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.
Founder Fridays
Check out my other email Founder Fridays — a Friday morning briefing helping startup founders and operators scale smarter.
Weekend Wisdom
Be Water, My Friend. Empty your mind. Be formless, shapeless, like water. You put water into a cup, it becomes the cup. You put water into a bottle, it becomes the bottle. You put it into a teapot, it becomes the teapot. Now water can flow or it can crash. Be water, my friend. -Bruce Lee