Breaking Rules in the Age of AI

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Anand S

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Feb 1, 2026, 7:26:15 PM (2 days ago) Feb 1
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Several educators have AI-enabled their courses, like:

  1. David Malan at Harvard CS50 provides an AI-powered "rubber duck debugger" trained on course-specific materials.
  2. Mohan Paturi at UC San Diego has deployed AI-tutors to his students.
  3. Ethan Mollick at Wharton uses AI as tutor, coach, teammate, simulator, even student, and runs simulations.
  4. Jeremy Howard's Fast.ai encourages students to use LLMs to write code, with a strict verification loop.
  5. Andrew Ng DeepLearning.AI integrates a chatbot into the platform, next to code cells, to handle syntax errors and beginner questions.

But no one seems to have eliminated reading material, nor added an "Ask AI" button to solve each question, nor run it at my scale (~3,000 students annually).

Nice, but what should I teach in the age of AI?

Simon Willison led me to Matt Webb led me to Milan Cvitkovic led me to think about assumptions and things we assume we can't do.

We've taught students a lot of "learned helplessness", like:

  • You can't ask dumb questions
  • You can't use AI for help
  • You can't fail
  • You can't change direction mid-way
  • You can't solve without knowing
  • You can't question the teacher
  • You can't ask others for help
  • You can't delegate boring stuff

These aren't bad lessons. But doing the opposite (and knowing when to) is also an important skill for the AI age.

So, in my course, this term, students will also be taught that:

  • You CAN ask dumb questions. Every question has newbie prompts like "Why should I study this?" or "Why THIS tool?" or "Can you explain that in Marathi?". Ask away!
  • You CAN use AI for help. Every question has an "Ask AI" button. Click on it. If it gives you the answer directly, great! Copy-paste it and save yourself time. If it doesn't figure it out!
  • You CAN fail. Try an answer: you get an immediate response. If it doesn't work, try again. And again.
  • You CAN change direction mid-way. Some questions will guide you down a path that won't work. Change direction. Try something else.
  • You CAN solve without knowing. Some questions will be in foreign languages. Some will be "out of syllabus". Some will be "beyond your level". Use AI to bridge the gap!
  • You CAN question the teacher. Some questions will be wrong, literally unsolveable as stated. Some questions will be ambiguous. Some won't even have a question. That's life. Your client and boss will do that too. Solve it anyway!
  • You CAN ask others for help. Some questions are broken into parts. Different people get different parts. Find your team and ask for help (or hide your work and game, learn politics!)
  • You CAN delegate boring stuff. There's no restriction on having AI (or anyone else) do any part of the course for you. If it's boring, and you can get someone to do it, delegate!

Since AI can solve so many problems, let's learn to break some rules and ask impossible questions to our AI overlords?

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