Limits of rationality
Humans don't reason their way to decisions. They decide, then reason.
People make decisions by reasoning through them logically.
People decide first, on instinct, then construct a logical sounding justification afterwards.
This is the largest theme in the archive, and its throughline is a sustained attack on the idea that people are, or should be, logical actors. Sutherland's central image is Jonathan Haidt's rider and elephant: the conscious, verbal mind doesn't drive behaviour so much as trail behind it, constructing plausible sounding justifications for decisions the elephant already made. The brain, in his line, is "the press office" of the self, not the "oval office."
He treats this as structurally reinforced by institutions: "no one ever gets fired for being logical," so businesses systematically prefer safe, deterministic, spreadsheet legible choices over better probabilistic ones, even though he calls business itself "a casino." Free markets, in his framing, are valuable precisely because they're a vast, decentralised experiment that lets millions of small irrational preferences average out into something smarter than any individual plan. Money, in his phrase, is "a truth drug."
A worldview built entirely on human irrationality struggles to explain why markets, institutions, and evolution produce outcomes that work as well as they demonstrably do. Either people are rational enough, often enough, for coordination to function, or irrationality is doing less explanatory work than a different, harder to formalise logic.
846 verified insights in this theme
846 verified insights in this theme
Rory contrasts average speed cameras (a well-defined objective with room for judgment) with fixed speed cameras (a rigid rule), building toward a critique of over-quantified management.
Rory argues that capitalism works by giving people clear objectives with latitude in how they're achieved, and that over-quantification destroys that latitude.
Rory, agreeing with Faris Aranki's account of being penalized as a junior consultant for relationship-building instead of billable modeling work, criticizes the big consulting firms' incentive structure.
On why people resist doing things differently even when it would benefit them.
On people using AI chatbots like a horoscope or oracle to offload a hard decision.
On why people distrust a human expert's gut instinct but readily trust an AI's.
On large companies sacrificing genuine long-term profitability for short-term quarterly optics.
On the pattern where a convenience (self-checkout, parking apps) becomes a forced default.
On an unintended consequence of supermarket self-checkout machines.
On why marketing data can't simply be centralized into one clean cause-and-effect dashboard.
On the limits of building a data dashboard that claims to model complex human behaviour.
On the gap between what people say in surveys and what they actually do — stated vs. revealed preference.
Explaining why a low-fat biscuit that tasted identical still sold worse once labelled 'low fat.'
On why low-calorie ice cream, despite sounding like an ideal product, has never really succeeded.
On an AI image classifier (per an anecdote from Tim Harford) that hallucinated an animal in pure white noise, and the human parallel (pareidolia).
On why businesses systematically underinvest in retention and customer experience relative to acquisition.
On why business decisions get dressed up in rational-looking process rather than admitted as subjective or intuitive.
On the advertising industry's need to pretend it follows a linear process when the real work is genuinely iterative and unpredictable.
Opening his answer on why innovation adoption is slower than we remember it being.
Describing what Edward Jenner had to overcome after developing the smallpox vaccine, as an example of resistance any new idea faces.
Illustrating slow technology adoption with a personal memory of being shouted at for using an early mobile phone in public.
Explaining why almost no electric-car owners would revert to fossil-fuel cars, arguing the appeal isn't primarily environmental.
Rory distinguishes stated from revealed preference while explaining why AI trained on what people say may miss what people actually want.
Rory summarizes the limitation of AI trained only on historical data, contrasting human awareness of gaps in knowledge with AI's blindness to what it hasn't seen.
Rory argues that admitting uncertainty about AI is a more effective leadership move than projecting false confidence, addressing the audience of HR executives.
Explaining why data-driven decision-making has an inherent bias toward the status quo.
Continuing the point that all data comes from the past, so data-driven approaches skew toward preserving the status quo.
Describing how people cherry-pick data to win arguments or defend themselves rather than to solve problems.
On quantification bias in organizational data — some things are measurable and so get weighted more heavily.
Arguing that psychological/attention-based solutions are systematically underweighted in business because they're not the most profitable or measurable focus.
Warning that whichever part of a business controls AI adoption determines whether it's used for savings or growth.
Arguing procurement gets credit for cost savings but is never held responsible for the value or opportunities it destroys.
Naming the business functions he sees as structurally risk-averse and resistant to opportunity-seeking.
Making the point (crediting an unnamed colleague for the original framing) that B2B decisions carry personal career risk that B2C ones don't.
Continuing the B2B-vs-B2C point: B2B decisions require documented justification to avoid personal blame.
Citing a finding on short-termism in corporate decision-making.
Explaining why family-owned and founder-led businesses are less prone to short-term thinking.
On why people default to benchmarking themselves against others despite its limitations.
Introducing an evolutionary-psychology idea about self-deception in explaining our own behavior.
Arguing experimentation and paying for things reveal what people actually want, unlike stated preferences.
Critiquing mainstream economics for ignoring non-monetary value creation like barter and favors.
Continuing the critique of finance-driven thinking's blindness to symbolic and relational value.
Answering a rapid-fire question about where he gets inspiration; his own summary of Ogilvy's description, not a verbatim Ogilvy quote.
Rory explaining why Uber's map view feels better than waiting blind for a cab.
Rory's summary principle of human decision-making, tied to menu design.
Rory on customers post-rationalizing their likes and dislikes.
Rory on the limits of customer research, before the TripAdvisor one-star-review example.
Rory introducing the Benjamin Franklin effect.
Rory explaining the Benjamin Franklin effect applied to guest requests.
Rory continuing on the Benjamin Franklin effect and guest requests.
Rory on culture and team-based evaluation, following the David Ogilvy anecdote.
Rory describing the fair, self-policing culture of a high-performing team (via The Pit TV analogy).
Rory on how advertising pitch teams naturally divide labor.
Rory summarizing his point about team-based versus individual measurement, citing Shackleton's Antarctic crew selection.
Rory's example of optimizing for group morale over individual metrics.
Rory on the limited tools available to financially-justified businesses.
Rory's example of farmers markets defying economic logic.
Opening framing of the tension between relational marketing and financial metrics.
Explaining why obvious business insights stay hidden.
Rory recounting advice he gave a client agonizing over commercial innovation.
On why organizations over-plan instead of experimenting.
Contrasting financial metrics with the true, longer-term value of a customer relationship.
Using the marriage analogy to explain why not every business transaction should be measured individually.
On why businesses underinvest in retention relative to acquisition.
On the structural bias toward transactional over relational business investment.
Discussing the AO bear gift and the case for actions that aren't immediately measurable.
Explaining why Amazon Prime's commitment mechanic appeals to consumers.
On the asymmetry between how marketing's costs and value are accounted for.
On why subscriptions were never actually popular with consumers, using the mobile phone industry as evidence.
On the unmeasurable but real effects of the Kagi refund policy.
On the origin of the subscription-economy push.
On subscription saturation among consumers.
Illustrating consumer wariness of forgotten subscriptions with a humorous example.
On subscription saturation as a barrier to new streaming entrants.
On consumers paying more for the psychological comfort of flexibility.
On his argument with a rail company about the psychological unfairness of flat-rate season tickets.
On the historical, technical origin of the subscription business model.
On why cheap, effective tactics like brand partnerships get overlooked in big organizations.
Rory's mea culpa about early-career ad-agency dogma against brand partnerships.
Explaining why Uber's success was a psychological transformation rather than an operational one.
On businesses' systematic bias toward objective over subjective measures.
Following the Churchill salt-shaker story, on why psychology's fuzziness is also its strength.
Contrasting marketing's "less wrong" logic with the single-right-answer mindset of exam maths.
On where the real risk of AI adoption originates.
On counterfactual comparison and Olympic medal outcomes.
On why subscription businesses design friction into cancellation.
On the perverse effects of tying pay and performance to fixed metrics.
On how free-holiday incentives compromise travel journalism's credibility.
Recounting Daniel Kahneman's private view on why comparison-heavy careers undermine happiness.
Rory on his general approach to understanding business and human behavior, contrasting physics-style theorizing with observational, evolutionary-style thinking.
Rory continuing the Newton/Darwin contrast, on how to approach complexity.
Rory continuing the Newton/Darwin contrast, on how to approach complexity.
Rory on how consumers actually make decisions, contra rational-actor models.
Rory on entrepreneurial and professional bravery.
Rory on the non-rational nature of much consumer spending.
Rory on why mathematicians have more free time than other science students.
Rory's petrol-cost-versus-porter-tip anecdote, illustrating the incoherence of the utility model of spending.
Rory's critique of economics' assumption of a consistent internal value-measuring device.
Rory on what hospitality work teaches about how a business really functions.
Rory on his own emotional reaction to avoidable versus unavoidable pain, tying to his interest in UX design.