Any Game but Chess

At the 1998 Berkshire Hathaway Annual Meeting, Warren Buffett was making a point about competition when he said:

"Somebody said, 'How do you beat Bobby Fischer?' You play him in any game except chess."

He was talking about investing. But the line applies more broadly — especially to founders and executives navigating crowded markets and competitive organizations.

Before you commit capital, brand, time, or political equity, there’s a more fundamental question than “Can we win?”

It’s: Whose game are we playing?

Because winning inside someone else’s frame is far harder than most operators admit.

The Startup Version

Startups do this constantly. They enter a category where an incumbent has already defined the terms: what "good" looks like, what gets measured, what buyers compare, what belongs in the demo, what pricing feels standard.

Then the challenger declares:, "We're better."

Better how? Faster. Cheaper. More features. More AI.

That's chess.

That's playing inside someone else's frame — where the incumbent has years of distribution, credibility, and buyer muscle memory accumulated on their side. Even if your product is superior you're asking the market to expend effort to re-evaluate assumptions.. Markets are efficient. They resist unnecessary effort. And extra risk.

I wrote about this in Don't Accept the Defaults — how the danger of defaults isn't that they're wrong, but that they're invisible. Category defaults work the same way. The incumbent set the benchmarks. Everyone else inherited them. Now you're being graded on a rubric you didn't write.

The real job isn't crafting a more polished story about the same category.

The real job is defining the terms under which you can win.

That often requires reframing the conversation away from the incumbent's strengths and toward outcomes where you hold structural advantage. Not "we do what they do, but better." More like: you've been measuring the wrong thing.

Many benchmarks are proxies, not outcomes.  Category language can obscure the underlying problem. Buyers believe they are optimizing for success when they are merely optimizing for convenience.

That's not a marketing spin. That's strategic positioning. It's choosing a different game.

The Career Version

Organizations operate the same way.

Every company has an implicit scoreboard: responsiveness, visibility, meeting performance, executive fluency, velocity of shipping — even when what’s shipped is misaligned.

If those are the rules of the game, you can either get better at those rules or find a different game.

This isn't a moral judgment. It's an allocation decision.

If you're wired for deep work — building, fixing, designing, synthesizing — some environments that reward performative busyness will undervalue you. That doesn't mean you're not valuable or lack talent. It means you're in the wrong tournament.

In Fast Isn't the Point, I told the story about the racquetball player at the BQE Racquet Club who destroyed me — not because he outpaced me, but out-positioned me.  He played a different game than I did. Every shot had intent.. He never moved more than necessary. I chased everything. He conserved energy and dictated tempo. He was barely sweating.

That's the Buffett principle in action. He wasn't better at my game. He was playing his own.

The Quiet Trap

The danger of playing  chess matches you didn't choose is that they start to feel like reality. If you lose, you assume you're losing in life.

You're not.

You're losing at their scoring system optimized for stability, politics, risk avoidance, loyalty, proximity to power. Those incentives are not inherently wrong. But they may not align with innovation, autonomy or long-term leverage.

One of the most consequential roles of my career started with no default at all — no template, no job description. The ambiguity was disorienting. It was also liberating. It forced me to define success on my own terms. That role helped me create an entirely new function that took a company from scrappy startup to IPO. It happened because I wasn't playing someone else's chess match. I was playing a game where my particular wiring — connecting dots across functions, seeing patterns, building from ambiguity — was the advantage.

The advantage was not superior execution within someone else’s mold. It was the absence of the mold.

Two Questions

Whether you are competing in a market or navigating your own career, two questions clarify everything:

1. What game am I actually being asked to play?
   Not the JD. Not the category slide. The actual game.
   

2. If I win at this game, do I get what I want?
   Autonomy. Leverage. Learning. Growth. Sanity.

Because some games let you win and still lose. That's the quiet trap.

The Move

For companies: Stop saying you're better. Start showing the buyer what they're measuring wrong. And back it with proof that doesn't require trust.

For individuals: Stop optimizing to be impressive. Start optimizing to be valuable in a way that travels. As I wrote in People Like Bad Pizza, what matters isn't the absolute — it's the context. Portable value is leverage.

Context-bound value is dependency. 

Berkson's Bits

Technology rarely is the solution to a problem. It's part of a solution. Tools help you do things. If the things you are trying to do don't make sense, they'll still help you do them.

What I'm Listening To...

I don't quite know how this jam-funk band showed up in my Youtube Music feed but I've got Don't Get Comfy buy Hot Like Mars on repeat right now. Well, maybe I do know. I hope you like it as much as I do.

You don't beat Bobby Fischer at chess.

You win by refusing to play chess.

Once that distinction is clear, competition looks different. Not because the competition disappears or the job gets easier — but because you stop letting someone else's scoreboard tell you whether you're winning.

Looking forward to continuing the conversation…

Alan