Mastering Strategy
A curated collection of articles, stories, and exercises to deepen your understanding of Guidepost Five: The Power of Strategy
What’s New
Next Sunday? The Explorer’s feeling restless, the Navigator keeps redrawing the map, and the Workhorse is hauling dead weight—and none of them knows why. In Guidepost Six: The Power of Vacuum, they finally realize they’ve been dragging around clutter they didn’t even know was there. Clear space, clear mind, and suddenly? Everyone starts pulling in the same direction. If you don’t want to miss it—be sure you’re subscribed.
The Journey so Far
Navigating a Whackadoodle World: Episode Five
What’s the difference between knowing how to move the chess pieces—and knowing how to win the game? In this sharp, often funny exploration of strategy vs. tactics, our favorite tutor-student duo tackles everything from confused metaphors to real-world disasters. With Hurricane Ian as a case study and personal beliefs as the underlying terrain, this episode digs into what it takes to build a life—or a city—with vision, clarity, and a map that actually matches the territory. Strategy starts here. Ready to question your compass?
Navigating a Whackadoodle World: Episode 19; or Strategies and tactics don’t always lead to good, do they?
When is a goal not a strategy? When it’s “stay out of jail.” In this sharp, unsettling, and darkly funny exchange, the girl wrestles with the difference between tactics and strategy—and why it matters who’s using them, and to what end. Through branding, gaslighting, media manipulation, and fake apologies, they dissect the methods of a certain president—and land on a sobering truth: not all strategies aim for good. What matters most is the goal you're aiming for... and the map you're using to get there.
Navigating a Whackadoodle World: Episode 34, or Why the creative mind is the first step in strategy
What if strategy isn’t a grind—but a creative act? In this wry, revealing dialogue, the girl confuses strategy with suffering, only to discover it’s really about curiosity, courage, and designing a life you actually want. From dream-building to SAT hacks, from travel goals to rethinking prayer, this conversation peels back the mystique around Guidepost Five: the Power of Strategy. Turns out, strategy isn’t about controlling the future—it’s about choosing it. And then daring to ask the right questions to get yourself there.
Guidepost Five: The Power of Strategy (Aka Episode 48)
When a looming economics paper threatens to tank her grade (and her spirit), the girl nearly gives up—until a story about strawberries turns into a deep dive into the Two Santa Claus Theory, Social Security, and the surprising link between curiosity and strategy. Along the way, she bumps into FDR, Reagan, and even Taylor Swift, all while wrestling with the question: what makes learning worth it? This week's guidepost—The Power of Strategy—gets a real-world workout, proving that research can be painful… but only if you forget to bring your explorer.
Navigating a Whackadoodle World: Episode 62, The Power of Strategy, or What to do when what you've been doing isn't working as you'd hoped
The student’s picked her major, but the tutor’s stuck—staring at her coffee and stewing over a subscriber who missed the point. Enter Guidepost Fourteen: The Power of Strategy. In a sharp role reversal, the girl calls out her tutor for failing to practice what she teaches. Strategy isn’t just planning—it’s adapting when your plan flops. With equal parts sass and wisdom, the student reminds her mentor that when the map doesn’t match the terrain, it’s time to redraw the map.