Curious
Learning to Be Wrong
The smartest people aren’t always right—they’re just the fastest to admit when they’re wrong.
Sean Oldham
Hi, I'm Sean! I'm the guy that writes stuff here. I have an interest in just about everything I come across and I like to share what I learn as often as I can. I hope you enjoy being here!
Scribble
The Strange Comfort of Typing Over Writing
Somewhere along the way, typing became the default, and my handwriting started feeling like a backup skill I haven’t practiced in years.
Design
The Most Useful Concept You’ve Never Heard Of
That door you pulled the wrong way? That wasn’t your fault. It was bad affordance design. Let’s talk about the hidden rules that shape the world.
Knowledge
What We Know and How We Know It
From tribal intuition to documented facts, knowledge takes many forms—and each one matters in different ways.
Thinking
Seeing the Future with Second-Order Thinking
Second-order thinking helps you make decisions that hold up over time by forcing you to ask not just “What happens?” but “What happens next?”
Philosophy
What Is Aesthetics? The Philosophy of Beauty and Art
Aesthetics is more than art theory. It’s how we make sense of beauty, taste, and the feelings that art awakens in us.
Productivity
What is Systems Thinking and How Can I Use it Today?
Systems thinking is a powerful mindset for understanding the world not as a series of isolated events, but as an interconnected web of relationships and influences. It invites us to see complexity clearly, to grasp how seemingly unrelated parts can work together, and to identify how small changes might have
Aviation
The Airport as a Microcosm of Human Systems
Every time I walk through an airport, I’m struck by the choreography of it all: families juggling suitcases, business travelers pacing during calls, signage trying to cut through a fog of fatigue and urgency. It’s easy to think of airports as simply functional infrastructure—a way to get
Aviation
How Aviation Embodies the Spirit of Continuous Exploration
There is something timeless and universal about humanity’s fascination with flight. From the moment people could look up and see birds soaring above them, the desire to join them became more than a fantasy—it became a calling. Flight has always symbolized freedom, ingenuity, and a kind of sublime
Work
What Game Designers Know that Corporate Leaders Forget
What if work felt more like a well-designed game? Lessons from game design that could transform how we lead, train, and manage.
Work
The Curse of Expertise
We tend to assume that the smartest people—the domain experts, the senior engineers, the seasoned leaders—are naturally the best ones to explain how things work. They’re the ones who know the system inside and out. But here’s the paradox: often, the more someone knows, the harder
Books
Book Review: Measure What Matters by John Doerr
Measure What Matters reframes leadership around focus, outcomes, and purpose—OKRs aren’t a tactic, they’re a mindset.