Lenny Rachitsky and Hilary Gridley have built a free, structured AI learning program modeled on Couch-to-5K, available at couchto5k.ai. The premise is direct: most people, from executives to students, are stuck at the "asking it questions" stage and cannot bridge the gap to workflows that actually return time. The program exists because that gap is a behavior change problem, not an information problem.
Gridley, who teaches AI-powered people management at Maven and writes on the subject at hils.substack.com, brings a product background spanning WHOOP, Dropbox, and Big Health. That history matters because the original article spends significant space on why behavior change fails before it explains how this program is designed to succeed. The structural reasoning is worth reading, not just the conclusion.
The full piece details the specific mechanics of how the program sequences AI skill-building to reduce friction and manufacture early wins, the same pattern used in consumer health products to move people from intention to habit. If you work in product, manage a team, or have told yourself you will get serious about AI next month, the original is worth your time.
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