The Cost of Contrarianism

Alistair Croll, co-author of Just Evil Enough and the mind behind Lean Analytics, has spent years mapping the architecture of subversive thinking. His framework is compelling: system awareness, a hunger for novelty, and what he calls disagreeability — the willingness to act without deference to received opinion. The Wilt Chamberlain story is his exhibit A. The greatest basketball player in history briefly abandoned the overhand free throw, adopted Rick Barry's granny-style underhand technique, and produced the best scoring season of his career. Then he stopped. Social shame overrode competitive logic. The lesson Croll draws is that sensitivity to public opinion is a liability.

It is a good story. It is also, on closer inspection, a story about an outlier so extreme as to be more of a cautionary tale than a general instruction.

Chamberlain did not adopt the underhand throw from a position of ordinary competitive parity. He entered the NBA having already forced a redrawing of the lane. The league banned him from passing over the backboard — not a metaphor, an actual rule change in response to a single man. His free throw problem existed precisely because opponents fouled him deliberately, knowing they could neutralize him no other way. The shame he eventually succumbed to was real, but the margin he was operating from was enormous. He could afford, at least for a time, to look ridiculous.

Most operators cannot. For a mid-market SaaS firm, a regional consultancy, or a government contractor with three active clients, reputational capital is not excess inventory. It is the working capital of the business. Public opprobrium does not arrive as gentle social pressure; it arrives as cancelled contracts, stalled procurement decisions, and the quiet removal of names from shortlists. The asymmetry matters. Chamberlain absorbed the cost of looking strange because his underlying performance made the experiment survivable. For companies without that margin, contrarian positioning is not a strategy so much as a wager on being right before the runway ends.

None of this renders Croll's framework useless. System awareness and a thirst for novelty remain genuinely transferable. But disagreeability, stripped of the dominance that made Chamberlain's experiment recoverable, is less a competitive asset than a tolerance for risk that most organisations are not actually priced to absorb.

The granny shot worked. That is not quite the same as saying anyone should take it.

What we’re into this week

Aaron

@Ana I know you’re not, but  I’m a sports fanatic, and this interview was just such fun for me. I’m having a lot of fun with Sports Viz Sunday right now—it’s like going to practice, but for my data skills. Anyone interested in data analytics should play around with this site.  

Ana

Look, it’s not that I don’t like sports; I just like playing them more than watching them. And this interview, with the re-drawing of rules because of one player’s dominance, reminds me of Robert Caro’s The Power Broker, which I’m reading right now. The book is about Robert Moses, who remade New York City from the 1920s-1960s, and how the city had to redraw the rules of engagement in the 1990s to avoid the kind of capture he created around himself. 

Scott

That’s dark, Ana. 

Ana

History is often dark, Scott! And New York recovered.

Scott

Fair enough, which is why I became a designer. Alistair’s position reminds me of the 2010s-era of media when I was at Vox and launching SB Nation. We were re-defining what media was and could be. We were launching, crashing, changing roles, doing it all again. We were never the Wilt Chamberlain of media, even though we thought we were. At the end of the day, the game is the way it is because it’s challenging. New ways of play can be introduced, new rules introduced to curb dominance, but the game is always tough, and, eventually, everyone retires. 

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Credits

Guest: Alistair Croll
Host: Aaron Meyers
Producer: Ana Monroe
Article: A Adams
Artwork: Saint James's Park, c. 1884/1886, James McNeill Whistler via the National Gallery
Why this artwork? Whistler shows just enough of the figures to evoke the place of the park and the activities going on there, but without giving any detail at all. I think that’s what Alistair is talking about when he’s talking about just evil enough, but not actually evil. Doing just enough to subvert a system so that your logic holds and others can follow it —Abi