The failure mode we're avoiding
The single biggest AI-fluency failure in the wild is not "bad prompts." It's delegating something you shouldn't have. You get a plausible output, you ship it, and months later you realize the output was making a decision you should have made.
So let's start Delegation with the negative: things to keep.
Four kinds of things to keep
1. Value judgments
"Is this opinion defensible?" "Is this tone kind?" "Is this trade-off fair?" An AI can draft, summarize, even critique — but the final value judgment is yours. Outsourcing it doesn't make it disappear; it just hides it.
2. Identity-shaping work
Anything that shapes who you are as a thinker:
- Writing that's genuinely yours — the voice and the argument.
- Original research framing — the question and the why.
- Creative work you want to grow into over decades.
Using AI to draft a boilerplate thank-you email is fine. Using AI to write your wedding toast is… a choice. Notice it.
3. Relational work
Anything where the process of doing it is part of the relationship:
- A hard conversation with a colleague.
- A letter to someone grieving.
- A code review where the discussion is more valuable than the fix.
AI can help you prepare. It should not be the thing that arrives.
4. Work you're learning from
If the point of a task is you getting better at something, delegating it is self-sabotage. A student who has AI write their proof has not practiced writing proofs. An engineer who has AI write their first Rust file has not learned Rust.
Notice this one carefully: it means sometimes less-capable you should do the work, on purpose, because the whole point is to become more capable.
A diagnostic question
Before delegating anything, ask: "If this came out perfectly, who gets better?"
- I get better → maybe keep it.
- The output gets better → delegate.
- Neither → why are you doing this at all?
Homework
Make two lists, on paper or in a note:
- "Don't delegate" — 5 specific tasks in your own life that you will not hand to AI, each with one reason.
- "Notice yourself wavering" — 3 tasks where you're tempted to delegate but you're not sure. We'll use these in the next lesson.
Short lesson. Important one.
Inspired by Anthropic's "AI Fluency: Framework & Foundations".