The things I was always too embarrassed to ask (and how I finally learned them) 🐾

The stock market, my medications, a period of history, and a creative skill. Four things I finally understand — and the four prompts that made it happen.

There are things I’ve wanted to understand for years. Things that came up in conversations and I nodded along, not quite sure I was following. Things I told myself I’d look into properly “someday” — and someday kept not arriving.

This year, AI ended my someday streak. Four times over.

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The stock market

I’ve had a retirement account for over twenty years. For most of that time I genuinely could not have explained to you how the stock market actually works — why it moves, what a bear market means, why everyone acts like the Federal Reserve is a weather system. I was too embarrassed to ask because I felt like I should already know. I asked AI to explain it starting from the most basic concept and building from there — and to check in after each section to see if I wanted to go deeper. It took three sessions and a lot of follow-up questions. I understand it now. Actually understand it.

My medications

My doctor has explained my medication interactions more than once. I always nodded and then forgot immediately. This time I asked AI to explain them in plain language — and I was very clear: not for medical advice, just to understand what my doctor has already told me so I can ask better questions. The analogy it used finally made something click that no one had explained to me that way before. I brought better questions to my next appointment.

A period of history I was always fuzzy on

The Cold War. I lived through part of it and never fully understood the full picture. I asked AI to tell me the story — conversationally, not as a summary — and to ask me what I wanted to explore next after each section. I spent three evenings on it. By the end I understood something I’d been vague about my entire adult life.

A creative skill I always wanted to try

Watercolor. I asked AI to be my teacher from absolute zero — what supplies I actually needed, what to learn first, what my first simple project should be. The supply list was much shorter than I expected. I haven’t become an artist. But I started. And that’s everything.

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All four prompts I used are in Sunday’s video and in Tuesday’s Substack post this week. But first I want to ask you:

What’s one thing you’ve always wanted to understand — and felt like you were too far behind to ask? Hit reply and tell me. It can be anything. Big or small. Academic or practical or completely personal. Your answer might become next week’s Wednesday post. 🐾

🎬 Watch Sunday’s video: I walk through all four learning moments live — the prompts, how each conversation went, and what I did with what I learned.

👉 Sunday video link

— Debbie
AI Puppy Playbook