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Have you used AI for planning, task breakdown?

I’ve been playing with using AI not for writing, but for planning – specifically, asking it to help break down big, fuzzy goals into concrete tasks.

Example: instead of “Launch new pricing page”, I’ll ask AI:
– List key steps from idea -> live on production
– What am I probably forgetting?
– Suggest a rough task tree for this

It’s not perfect, but I’ve noticed:
– it’s great at surfacing “obvious but easy to forget” steps
– it helps when my brain is tired and everything feels too big
– I still have to edit heavily, but it gives me a solid starting skeleton.

I’m curious how others feel about this:

↓↓↓↓↓↓↓↓↓↓↓↓↓↓↓↓↓
Have you tried using AI to help plan or break down projects (not just to generate text)?
– If yes, what actually worked for you?
– If no, is there a reason you’re avoiding it?

Would love to hear real experiences, not just "AI is hype" or "AI is magic" 🙂

on December 18, 2025
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    Hi Josh!

    I found AI to be useful as context tracker. Switching between projects adds significant overhead to remember what's done and what's in progress, and AI can be surprisingly helpful.

    What had worked:

    • Splitting plan development in bite-size chunks. AI can drift on vague scopes, just like humans :) First I draft high-level structure (the skeleton), then ask AI to bring details and consider edge cases on each part, one point per question. Easier to supervise, less hallucinations. Be sure to include software/hardware constrains so it won't guess.
    • When plan is ready, I'm starting a new chat with that plan as the prompt, and add execution notes after each change (what's done, what needs correction, etc.). That allows to ask for summaries, next steps and pivot points on every step.
    • Tuning AI roles if necessary (architectural scope, implementation scope, testing scope). Important: when putting AI into some role, need to explicitly tell it to "get back" when changing the scope.

    Hope that helps!