All the devils

Wild Garden
4 min readJan 22, 2024

When you spend enough time being called a “planner” you might begin to ask some questions. What happens when my plans meet the real world? What can be planned?

My professional life involves frequent decision-making, but the single decision I make the most is where to surf this morning. That starts with a rough understanding of the forecast that I tend to look at 1–2 days ahead of time. Tide is the most predictable, then swell direction and height, then wind speed and direction. Then, the morning of, usually in the dark, I consider a few options. Factor in how I’m feeling that day, what kind of board I feel like riding, and I get to a decision of where to look first. By the time the sun comes up I’ve made a bet based on a model I’ve built in my head. I always surf, but my model is far from perfect; it’s very seldom exactly as I’ve pictured. My mornings are rather hopelessly attached to the mercurial whims of the North Pacific.

Yesterday afternoon on the Ventura coast

Mathematician Dan Rockmore recently wrote a piece for The New Yorker on the challenges of modeling when human factors are involved. In it he writes, “‘Art is the lie that makes us realize the truth,’ Picasso once said; the same could be said of mathematical modeling.” It’s the real world conflicting our projection of it.

I’ve been reading Annie Duke’s Thinking in Bets at the recommendation of my friend Brendon. (Normally he recommends books that are 1000+ pages and full of words with an average of four syllables each. I was relieved that this is not that.) Duke is a psychology PhD-dropout turned professional poker player who uses her experience in both fields to explore how we make decisions: “Thinking in bets starts with recognizing that there are exactly two things that determine how our lives turn out: the quality of our decisions and luck. Learning to recognize the difference between the two is what thinking in bets is all about.”

Her book made me think about a particularly buzzy topic at this point in history: Stanley cups. Having made the migration from TikTok to business news may foretell the peak of the brand whose revenue has increased 10x in five years (I’m no Nostradamus; search volume suggests we’re just past-peak Stanley).

Stanley search index, January 2023 to today

Culturally, this type of buzz is generally not sustainable:

Indeed, collabs have been key to driving the Stanley Quencher’s popularity. The Quencher is frequently released in limited edition colors that sell out in minutes. A recent collaboration with Starbucks resulted in a red Quencher that was being resold on eBay for hundreds of dollars the same day it dropped.

We move on to the next thing that says we’re culturally in-tune. See: Logan Paul and KSI’s PRIME, the energy drink that had people buying empty bottles for $35 last summer.

Prime Energy search index, January 2023 to today

But full credit to Stanley for bottling more buzz than most. What we should look at in cases like this: what was planned, and what was lucky?

The finance-led world of business buys metrics for a premium and luck on the cheap. It’s hard to predict future cash flows when you have to factor in luck. But there’s a sobriety, grit, and optimism to seeing business as a game that includes exogenous unknowns. As Duke writes, “Poker, in contrast [to chess], is a game of incomplete information. It is a game of decision-making under conditions of uncertainty over time. (Not coincidentally, that is close to the definition of game theory.)”

As Shakespeare said in The Tempest, “Hell is empty and all the devils are here.” The factors we need to make decisions all exist and some of them are, paradoxically, known unknowns.

Though I’d like to believe that I can get my surf forecast game to 100% accuracy, I’m not willing to bet on it. If I’m going to keep scoring, I need to risk a few days where I sit in the water retooling my model.

I write these posts, 3-MINUTE MONDAYS, every other week. My goal with them is to share a snippet of insight into how to do strategy, build teams, and grow. Comment here or message me on LinkedIn if you want to chat. — Ben

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Wild Garden

Wild Garden is an exploration of how companies use strategy, creativity, and organizational culture to nurture growth. Organically fertilized by Ben Perreira.