Unsettling Questions That Disrupt Comfortable Certainties
Created at: August 10, 2025
Ask the question that unsettles your comfortable answers. — Zadie Smith
Discomfort as an Intellectual Compass
Zadie Smith's challenge urges us to treat unease as a guide rather than a threat. Comfortable answers can calcify into identity; the unsettling question breaks that crust so curiosity can breathe again. In essays like "Feel Free" (2018) and "Speaking in Tongues" (2008), Smith celebrates ambivalence and plurality, implying that a single, soothing narrative is rarely sufficient. Thus the task is not to humiliate our past selves, but to keep widening the room in which our thinking happens.
Socratic Roots of Fruitful Doubt
The lineage of this impulse runs back to Socrates, whose elenchus unsettled his interlocutors until their certainties collapsed. In Plato's "Apology" (c. 399 BC), he defends this practice as a civic duty, a way to expose unexamined assumptions masquerading as knowledge. Later, Rainer Maria Rilke advised to "live the questions" in Letters to a Young Poet (1903), shifting the focus from quick solutions to sustained inquiry. Together they suggest that disturbance, handled with care, is not cruelty but a public service.
Science Advances by Asking Against Itself
Modern science institutionalized this ethic. Karl Popper's "Conjectures and Refutations" (1963) holds that knowledge grows when we court falsification rather than confirmation, while Thomas Kuhn's "The Structure of Scientific Revolutions" (1962) shows how anomalies pry open new paradigms. A vivid example is Ignaz Semmelweis, who in 1847 asked why physician-run maternity wards had higher mortality than midwife-run ones; his unsettling answer—wash hands—clashed with comfortable miasma theories but saved lives. In short, progress favors questions that risk our pride.
Outsmarting Our Certainty Biases
Psychology explains why Smith's advice feels hard. Confirmation bias steers us toward agreeable data (see Nickerson, Psychological Bulletin, 1998), while motivated reasoning lets identity filter evidence (Kunda, Psychological Bulletin, 1990). The Dunning-Kruger effect warns that low skill can inflate confidence (Kruger & Dunning, JPSP, 1999). To counter these, we can steelman opposing views, seek disconfirming facts first, and borrow from Tetlock's "Superforecasting" (2015): ask what would change our mind and assign probabilities rather than absolutes.
Designing for Dissent Before Disaster
In practice, organizations can encode unsettling questions into routine. Toyota's "Five Whys" (Ohno, 1988) pushes teams past superficial fixes, while Gary Klein's premortem (HBR, 2007) asks, "It is one year later and the project failed—what happened?" The stakes are stark in the Challenger accident (1986), where engineer Roger Boisjoly's concerns about O-ring performance in cold weather were sidelined. Cultures that normalize stopping the line turn private doubt into collective safety.
Journalism, Literature, and Public Courage
Beyond labs and factories, public life depends on those who pose unsettling questions aloud. James Baldwin noted, "Not everything that is faced can be changed, but nothing can be changed until it is faced" (1962), a credo for reporting and critique. Hannah Arendt's "Truth and Politics" (1967) similarly defends inconvenient facts against comforting fiction. Smith's own novel "On Beauty" (2005) stages clashes of aesthetic and moral certainty, inviting readers to inhabit rival truths long enough to soften their own.
Ethics of Asking Without Wounding
Yet disturbance must be humane. Cognitive therapy uses Socratic questioning to gently examine catastrophic thoughts (Beck, 1979), modeling how to challenge without shaming. In groups, Amy Edmondson's research on psychological safety (The Fearless Organization, 2019) shows that people speak up when leaders admit fallibility and reward dissent. The ethical rule is simple: aim the question at the idea, not the person; signal curiosity, not conquest; and leave the other side with more dignity than you found.
Everyday Prompts to Stretch Your Frame
Finally, a practice emerges. Begin where comfort whispers: ask, "What would prove me wrong?" Then widen, "What am I not seeing because it would inconvenience me?" Close with generosity, "What is the strongest case against my position, and what can I adopt from it today?" As these questions loop, answers feel less like fortresses and more like tents—portable, revisable, and open to the weather of new evidence.