Repetition won’t save you in a wicked world

In many classrooms, students race through problems with the same worksheet over and over, convinced repetition is the golden ticket. In a physics lab, technicians practice identical calibrations until they’re flawless. These are “kind” environments: rules are clear, mistakes obvious, and improvement follows simple pattern recognition. Now imagine a start-up pivoting on product-market fit or a manager solving unrest on a team with no precedent. That’s a “wicked” world, where rules shift and feedback is murky. Here, drilling the same task harder may only reinforce the wrong habits. Our brains default to what feels easiest—repeat what we know—but that can blind us when challenges evolve.

Psychologists Daniel Kahneman and Robin Hogarth call this the difference between kind and wicked domains. In kind settings, skill grows by repeating the same moves: chess tactics or golf swings. In wicked settings, success demands variety—conceptual thinking, cross-domain analogies, and experimentation. Struggling with multiple contexts seeds the flexible mind, while excessive ease can breed brittle expertise. In other words, your next big leap often lies not in doing more of the same, but in doing it differently.

If you’re stuck on a wicked challenge—say, revamping company culture or mastering a new language—adding more practice on the same failed method will feel comfortable but won’t stick. Instead, you need spaced, varied trials, mixing formats, asking open questions, and testing ideas in new arenas. That kind of “desirable difficulty” forces you to extract the underlying principles, making your learning both deeper and more transferable. Over time, you become less reactive and more strategic, able to match thinking to novel problems rather than falling back on rote routines.

You’ve already started sorting tasks by ease versus complexity, and that insight alone can transform how you learn. Now, when you face a new challenge, quickly write down whether it’s kind—where perfect repetition works—or wicked—where patterns shift and rules aren’t clear. For wicked tasks, change environments, tweak your methods, and embrace small failures to force deeper understanding. For kind tasks, carve out focused time blocks for deliberate practice, repeating the right action until it becomes second nature. This simple mapping of tasks to strategies will reshape your progress, making you more agile in yesterday’s storms and tomorrow’s unknowns.