Weekend Briefing No. 583
The Big Lie of Strategic Planning -- Reasoning From First Principles -- College’s Tragic Decline
Welcome to the weekend.
Prime Numbers
49 — A recent survey shows Americans are most supportive of adding former President Theodore Roosevelt and Dr. Martin Luther King Jr. (both 49%) to redesigned currency, while only 24% support Albert Einstein.
77 — According to a recent poll, 77% of Americans believe artists, writers, musicians and creators should be asked for consent before their work is used to train AI, highlighting strong public support for creator rights in the AI era.
60 — A recent report reveals alarming honeybee losses with U.S. commercial beekeepers experiencing 60%-100% hive losses, while highlighting that North America has 4,000 native bee species, including the solitary mason bee that could potentially serve as an alternative pollinator.
The Big Lie of Strategic Planning
True strategy isn't about comfortable planning but about making difficult choices under uncertainty. Instead of falling into the traps of strategic planning, cost-based thinking or self-referential frameworks, effective strategists focus on making clear decisions about where to play and how to win with customers. The best strategies can be summarized on a single page and make explicit logic behind key choices, testing assumptions against real-world outcomes as they unfold. Embrace being uncomfortable with your strategy — if you're entirely comfortable, you're probably not making the tough choices needed for competitive advantage. Harvard Business Review (7 minutes)
Reasoning From First Principles
If you spend a lot of time in tech, you'll inevitably hear people extolling the virtues of being a First Principles Thinker — that is, someone who analyzes situations in terms of foundational axioms and then uses their impeccable reasoning to determine a bold and original course of action. But if you've spent significant time operating a business, it's obvious that the solutions to your problems are rarely unique. The optimal approach breaks down this false dichotomy: reason from first principles to establish what your problems actually are, then reason from analogy to figure out what solutions you should deploy. This powerful combination requires humility — acknowledging that while your challenges might need methodical diagnosis, drawing from existing solution frameworks allows for faster implementation and multiple correction attempts. Stay SaaSy (4 minutes)
Skip the Tax Deadline
The approaching tax deadline can create significant pressure, but filing for an extension offers crucial breathing room and strategic advantages. An extension formally grants you additional months to file your complete tax return, although — critically — it does not extend the time to pay any taxes you anticipate owing. Utilizing an extension isn't merely delaying the inevitable; it's a strategic move allowing for meticulous record compilation, thoughtful consideration of deductions and credits, and avoidance of rushed errors that could prove costly. The tax code does not explicitly provide for a taxpayer to file an amendment or for the IRS to accept the amendment if you knowingly file an incorrect return only to amend it later. Neglecting to file either your return or an extension by the deadline results in substantial failure-to-file penalties, often far exceeding penalties for late payment. TaxFrame doesn't just submit extension forms — they help you accurately estimate your tax liability to minimize potential penalties and strategically use the extra time to ensure your final return is optimized for the best possible outcome. Avoid unnecessary stress and penalties — schedule a consultation today to navigate the deadline wisely. TaxFrame (Sponsored)
College’s Tragic Decline
If you spend time in academia today, you'll witness a shocking transformation in college students who increasingly struggle with basic literacy, critical thinking and sustained attention. The average student at a regional public university can't comprehend serious adult novels, writes at an eighth-grade level, routinely skips classes and cannot disconnect from their phones even for a 50-minute lecture. Technology addiction has created a generation of disengaged learners who view education as purely transactional, treating attendance as optional and expecting professors to accommodate their unwillingness to engage with course material. This isn't merely generational complaining — it represents a profound societal shift leaving educators caught between maintaining standards and meeting students "where they are," ultimately creating a pervasive sadness among faculty watching the traditional university experience deteriorate. Scriptorium Philosophia (6 minutes)
The Comedown Effect
The euphoria of accomplishment often gives way to an unexpected emotional void as our dopamine-driven brain, which thrives on anticipation rather than attainment, dramatically reduces its neurochemical rewards once a goal is reached. This "comedown effect" creates a neurological withdrawal that can feel like emptiness, especially when we've become accustomed to measuring our worth through external validation rather than intrinsic satisfaction. Managing this natural reset requires intentional strategies — creating transition rituals, reflective integration, small novel experiments, refocusing on internal values and gently exploring future possibilities without immediate commitment. Understanding that discomfort is part of our growth cycle helps us develop dual awareness: celebrating achievements while recognizing that our most meaningful experiences come from the continuous journey of curiosity and learning rather than from reaching final destinations. Ness Labs (6 minutes)
Prediction's Paradox
While science fiction writers completely failed to predict the internet before its arrival, they obsessively imagined artificial intelligence for over a century — almost exclusively through cautionary tales of robot uprisings and humanity's downfall. This asymmetry between "expected" technologies (like AI, which we've long anticipated with fear) and "unexpected" ones (like the internet, which arrived without cultural preparation) helps explain today's public anxiety toward AI, which exists not because of actual experience but because our cultural imagination lacks positive models for superintelligent machines. The premature attempts to regulate AI stem from this lopsided worry about imagined harms, yet such regulation is unlikely to succeed precisely because we don't know what the real impacts will be despite our extensive speculation. Instead of continuing this century-long rehearsal of AI catastrophes, we should redirect our imaginative energy toward envisioning AI's potential benefits and — perhaps more importantly — identifying the next wave of truly unexpected technologies that might be just around the corner. The Technium (4 minutes)
Pure Independence
Achieving independence — whether through a shy child ordering ice cream alone or an adult building financial freedom — creates a psychological reward far more powerful than any accomplishment achieved under supervision. True independence extends beyond finances to encompass intellectual and moral autonomy, freeing you from the exhausting burden of seeking validation from strangers while allowing you to strategically choose whose opinions truly matter. When independent, you're not accountable to anyone but yourself — a state where most people produce their most creative and fulfilling work. The greatest irony is that some who appear financially independent remain completely controlled by money, spending their days doing things they'd rather not because money dictates their choices instead of them using money as the tool it should be. Collab Fund (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.
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Weekend Wisdom
Do what you can, with what you have, where you are. -Teddy Roosevelt