Puzzled

Anybody who knows me knows I love word games. When a hangout stalls, I pull people into idiom charades. If the AirBnB comes stocked with a games closet, I will insist on playing Codenames or Scrabble.

But above all else, I love the New York Times Crossword.

Between daily meetings when my stacked calendar coughs up fifteen free minutes, I instinctively type out nyt… My browser autocompletes and takes me to nytimes.com/crosswords. I start by banging out the Mini, a scowl forming whenever it takes longer than twenty-five seconds. But when that last letter drops and the grid celebrates… pure bliss.

No stakeholder alignment. No "let's circle back." Just binary certainty in a world built on maybe.

For exactly three seconds after I complete a crossword puzzle, the world makes complete sense.

I don't remember exactly how I first got into crosswords. I do remember plenty of hungover mornings in college when my roommates and I would gather on someone's bed, one of us plugging a laptop into the HDMI cord and sitting on the floor next to the TV so everyone could see. We'd steer through a puzzle together before dragging ourselves to brunch.

Even today, my cofounder and I still set aside fifteen minutes most afternoons to do the daily crossword on Zoom. No talk about fundraising or headcount, just a screenshare and flow-state collaboration.

The draw isn’t nostalgia or vocabulary building. It’s precision and satisfaction. Crosswords offer what life withholds: a bounded problem with a correct answer.

Work, relationships, politics, money, mortality… none of the hard parts of living yield clean, non-negotiable solutions. The crossword does. Everything eventually fits. Perfection appears, however briefly.

I feel wired to worship that feeling. I keep a carefully manicured calendar. Crafting and executing a checklist gives me deep satisfaction. Inbox Zero is my religion.

These puzzles feed the same appetite for control, the same desperate need to force order onto chaos.

I'm hooked on that sensation: the rush of closure. The little dopamine surge when ambiguity collapses into certainty.

OBSESSION

That's the crossword's high. The aha is joinery. Ambiguity snapping into inevitability and the brain-itch finally scratched.

Crosswords work because they respect the architecture of satisfaction. Unlike the endless scroll of social feeds that scattershot novelty in random bursts, crosswords hoard the reward and deliver it as a single, concentrated hit when a corner unlocks.

The formula is precise:

This is how Wordle conquered the world in six weeks during peak pandemic uncertainty. One puzzle. Six guesses. Binary outcome. Share your grid. See you tomorrow.

We're so starved for completion and resolution that we'll manufacture it anywhere we can. Puzzles create artificial finish lines in a world that refuses to stop moving.

EUREKA

Every day I face decisions that affect my business. A choice between two product features. Both have merit. Both have data. Both have passionate advocates. In a crossword, one would fit and one wouldn't. In reality, both could work, neither might work, and we won't know for months.

Sometimes I get trapped here. I'll spend days constructing matrices and documentation, running scenarios, hunting for the "right" answer. My team waits or moves on. But I stay stuck, looking for that perfect fit, that satisfying click of certainty. It never comes.

Sometimes I think the crossword has made me worse at my job.

As a founder, I've overfit decisions, delayed calls, hunted for "perfect" options that don't exist. I've turned simple choices into complex puzzles, adding constraints until there's only one possible answer, then wondering why everything takes so long.

The crossword trained me to crave a perfect fit, but life rewards me for moving without it.

I've been thinking about this a lot lately. The puzzle rehearses one kind of excellence: precise thinking, clean closure, that moment of joinery. The rest of my day demands something else: making calls with incomplete data, building with materials that don't quite fit, accepting visible seams.

Leadership rewards direction under uncertainty, not waiting for crossings to confirm every square. The real world demands motion with partial information, iteration in public, peace with imperfection.

PARALYSIS

Maybe you have your own version of this addiction. A perfectly executed meal prep, iPhone apps filed into neat folders, a dishwasher loaded just right. All tiny islands of control in an ocean of ambiguity.

We tell ourselves these habits make us sharper. But they might be training us to wait for certainty that never comes, to seek perfect fits in a world built on compromise and visible seams.

I notice this pattern everywhere. Founders who rebuild financial models until they show exactly what they want to see. Job seekers who won't apply until their resumes are flawless. Singles who swipe endlessly, waiting for someone who checks every box. House hunters who tour dozens of places but can never pull the trigger.

We're all searching for that sense of certainty in places it can never exist.

The most successful operators I know seem to share a specific cognitive skill: comfort with permanent uncertainty. They make decisions with 60% information while completion-addicted minds are still gathering data, hoping to reach the 100% threshold that never arrives.

ORDER

My calendar tomorrow shows 7.5 hours of meetings. Each will end with more questions than answers. Product decisions that affect users. Hiring decisions that shape growth. Strategic choices with no clean solution. Team dynamics that resist any framework.

But I'll still make time for the crossword, stealing minutes to chase that joinery: the seam disappearing, the perfect slide. For a few moments, I get to live in a world where every problem has an answer, where persistence guarantees resolution, where that soft click of certainty is always just one more crossing away.

Then I'll close the tab and get back to building in a world where the pieces rarely fit.

I'm not sure I want to be cured of this addiction. These moments of artificial completion might be necessary maintenance for minds that spend most of their time navigating ambiguity.

All I know is at least I'm not into Sudoku. Those grids don't even pretend to mean anything.

UP AND TO THE RIGHT