Meet the philosopher outsmarting me since kindergarten

One of my best friends since we were five years old, Dr. Jeff Kaplan, gave the convocation speech at Williams College earlier this month.

Like all best friends, our shared language tends to be debate: we spar over movies, politics, even which back road will save two minutes in traffic. (He’s usually right, which is particularly annoying.)

After Williams, Jeff went on to Oxford, Cambridge, and then earned his PhD in philosophy at Berkeley, so it’s no surprise he now makes his living persuading people with reasoning. (I just wish he’d go easier on me at dinner parties.)

His speech, which I encourage you to watch, was classic Jeff: gripping, funny, and deeply thoughtful.

He told the story of Qantas Flight 32, when an Airbus A380 nearly fell out of the sky after a massive engine failure. The pilot, Richard De Crespigny, saved 440 passengers not only with technical skill, but with reasoning and communication — giving people reasons to believe they were safe rather than empty reassurances.

Jeff’s point was that this ability to reason clearly and change minds is one of the most powerful skills you can learn in college. Or as he put it: “The artful giving of reasons is the most underrated intellectual capacity that exists.” I’ve known this since the age of five — because he’s been using that underrated capacity against me for nearly four decades.

Key quote: “What reasons do — and what vague reassurances don’t — they satisfy. They make you feel full, like you’ve eaten enough. So if vague reassurances are so bad, and giving reasons is so good, then why is our world full of so much empty, unpersuasive blather? Why doesn’t everyone just explain and justify their decisions? They can’t. Explaining the reasons for a decision, marshaling facts in order to rationally persuade someone: that’s not usually taught in pilot training. It is sometimes, when we do it right, taught in a liberal arts education, in the laying out of evidence in the sciences and social sciences, in the careful presentation of argument in the humanities.”

AI, critical thinking, and the Vaughn Tan Rule

Cedric Chin is one of my favorite business writers. Based in Singapore, he runs Commoncog, a site devoted to how expertise really works. In his new essay, How to Use AI Without Becoming Stupid, he introduces the Vaughn Tan Rule: don’t outsource your value judgments to AI unless you have a clear reason.

This is a question I think about constantly — how do we use these tools without letting them use us? Cedric’s idea is simple. AIs can process and summarize, but they can’t make meaning. Only humans can decide what is good, worthwhile, or even beautiful.

Cedric shows how this plays out in real life. Teachers can use AI to cut grading time but still handle the hard feedback themselves. Hedge funds can use AI to spot contradictions in transcripts but still make the big calls.

The rule is a guardrail: use AI to save time, but keep the meaning-making for yourself. Or as Chin writes: “In a world of rapid AI development, building business policy around things that don’t change is worth its weight in gold.”

Key quote: “The point of giving you this explanation is to reassure you that there is some theoretical basis behind the Vaughn Tan Rule, and that this theoretical basis will not change. It is one of the sublime ironies of our current moment that while cutting-edge LLMs are the crowning achievement of machine learning (as STEM a field as any), the Vaughn Tan Rule is derived from the humanities.”

Outlast Field Notes: Lisbon, September 2025 — Inside the world’s oldest bookstore

In last week’s Nightcrawler, I mentioned I’d be in Lisbon. True to my word, I found myself standing inside Livraria Bertrand this week — the world’s oldest operating bookstore, founded in 1732.

The store feels less like a retail space and more like a time capsule. One employee explained that after the 1755 earthquake, Bertrand moved a few streets down for two decades before returning to this original room. Even today, the wooden panels along the back wall conceal a secret: during the Salazar dictatorship (1933-1974), staff hid forbidden books there. Now, those panels only hide dust — but the stories remain.

What struck me most is how Bertrand has survived by embracing, not denying, its history. You can literally smell the centuries in the paper and wood. The employee told me that the bookstore thrives partly because of its stamp: when you buy a book here, you can have it embossed with the mark of “the world’s oldest bookstore.” That small ritual transforms a purchase into a keepsake.

But heritage alone doesn’t explain Bertrand’s longevity. Location helps — it sits in a lively district of Lisbon, where tourists and locals mingle. So does a refusal to chase trends. “It’s about embracing our history without caring if people know,” the employee told me. At the same time, the store has deftly leveraged modern tools: social media and travel influencers have amplified its profile, driving sales upward in the past two to three years.

The contrast with American mega-booksellers is telling. Bertrand is smaller, but perhaps its very scale — and its intimacy — is part of why it still thrives.

To walk through Bertrand is to walk through layers of history: earthquakes, dictatorships, revolutions, and now a tourism boom fueled by Instagram. In the end, it’s not just books that Bertrand sells — it’s the feeling of endurance itself.

A few more links I enjoyed:

The Stubborn Genius of James Dyson – via David Senra / Founders

Key quote: “‍And if I had to summarize it into a single sentence, it would be: difference and retention of total control. This is one of the most important ideas that I’ve learned from James Dyson, one that has absolutely grabbed me and held onto me for six or seven years. It says difference for the sake of it — in everything from the moment the idea strikes to the running of the business. […] This principle of Dyson will be repeated across decades. He says, ‘I have sought out originality for its own sake. This is a philosophy which demands difference from what exists.’”

The Surprisingly Sophisticated Mind of an Insect – via Noema

Key quote: “‍However, a growing collection of new experiments is challenging the old consensus. Far from being six-legged automatons, they can experience feelings akin to pain and suffering, joy and desire. When [ecologist Lars] Chittka gave bumblebees an extra jolt of sucrose, their favorite food, the bees buzzed with delight. Agitated, anxious honeybees, on the other hand, responded with pessimism when researchers shook them to simulate a predatory attack. Other researchers found that they “scream” when under threat. Ants display rudimentary counting abilities, can understand the concept of zero and make tools. Fruit flies learn from their peers. Cockroaches have complex social lives. Fruit flies drown themselves in booze when deprived of mating opportunities. Some earwigs and other insects play dead when threatened by a predator. In other words, insects have thoughts and feelings. The next question for philosophers and scientists alike is: Do they have consciousness?”