To the Vector, Belong the Spoils
A love story about freedom, discipline, and knowing what you are
Earlier this week, deep in prep for a conference talk, I went down a rabbit hole that had nothing to do with the conference.
I found a cartoon. 1965. Oscar winner. Ten minutes long.
Go watch it. Right now. I mean it.
The Dot and the Line is a mid-century love story — orchestral staccatos, saturated colors, a narrator who sounds like he’s straight out of old-school Hollywood. The plot: a sensible straight line is hopelessly in love with a red dot. The dot is in love with a squiggle. The squiggle is... free.
The squiggle doesn’t do anything with the freedom. He just moves. Wherever. However. To a cocktail jazz soundtrack. Charming and chaotic and completely directionless. And the line, watching this, decides that’s what freedom looks like. So he tries it too.
He flails.
I’ve been an “official” entrepreneur (whatever that means) for about three months now. And the hardest thing (one I knew was coming, just not like this) isn’t necessarily the revenue or the clients or the grinding loneliness of building something from nothing.
It’s the constraints. Specifically: which ones to keep.
Twenty years in corporate teaches you a very particular set of rules about what is valuable, what is worth your time, what success looks like. Profit is the organizing principle. Growth is the metric. I didn’t agree with all of it. But I learned it. Internalized it. Built a career inside it.
And then I walked away.
Now I’m the squiggle. Free. Terrifying. Moving in any direction I want. Some days that feels like power. Some days it feels exactly like the line trying to imitate the squiggle.
Just flailing.
The line in the cartoon, however, figures something out, “For months he practiced sides, bends and angles…Before long he learned to…express himself in any shape he wished.”
I learned something like this at IDEO years ago. Design thinking lives inside a specific tension: diverge first, then converge. Go wide — really wide, no-wrong-answers wide — before you earn the right to focus. The divergence without convergence is just noise. Discipline in the craft AND discipline in the meaning.
The freedom is in knowing which constraints matter. Which ones are yours.
The cartoon calls the line a vector. A quantity with both magnitude and direction.
Not just movement — oriented movement.
Not just effort — directed effort.
That’s what I’m trying to build. Not a business that just moves, but one that knows why it’s moving and where. Grounded in what I actually believe about people and work and what’s worth doing. Not in what the market rewards this quarter or what my old corporate brain still insists is “real” value.
Don’t get me wrong. I still have to feed my family. And I’m incredibly clear on the fact that we’re all inside systems we didn’t make. Economic systems. Social systems. Information systems being rewritten in real time. None of us opted in. All of us are navigating.
The question is whether we know what we are inside those systems. Whether we have magnitude — something genuinely ours to offer — and direction — a reason for the offering that holds even when the signals change.
The squiggle has neither. The squiggle just moves.
To the vector, belong the spoils.
Amen.
P.S. Are you a squiggle right now, or a vector?
3 Things That Caught My Attention This Week
📝 My former boss, ex-IDEO Chief Creative Officer Paul Bennett, has been penning some glorious essays lately. His latest, on shared emotional geographies and the role of design in shaping how we feel, has taken up a permanent residence in my brain.
🎧 For my Spanish-speakers, Chisme Corporativo is my new favorite podcast to brush up on my “professional” vocabulary 😉 #iykyk — Dos chicas Mexicanas chismeando sobre el mundo empresarial.
💌 Profoundly obsessed with this project. Crossing Guard in Vermont starts snail mail club. It’s my dream creative side gig.