50 ChatGPT Prompts I Use Every Week

A free PDF with 50 specific, tested prompts organized into 8 categories — reading the fine print, negotiating bills, writing the email you've been avoiding, family logistics, small business work, and more. Designed to be skimmed first, bookmarked, and used week after week.

Download the PDF (free) ~100 KB · 6 pages · no email required

What's inside

50 prompts grouped into 8 everyday categories. These aren't "write me an email" templates — they're specific, tested prompts with the context-setting that makes AI actually useful.

• Reading things you wouldn't otherwise read
• Writing better emails
• Family and parenting
• Money and bills
• Small business and solopreneur
• Learning and explaining
• Decisions and research
• Time and productivity

Three sample prompts

To give you a feel for what's in the PDF — these three are pulled directly from it.

I'm going to paste a letter from my insurance company. Tell me, in plain English: (1) what they're actually saying, (2) what action — if any — I need to take, (3) the deadline if there is one, and (4) anything they've buried that I should push back on. Be specific, not generic. Here's the letter: [paste]

I need to reply to this message. The situation is [one-sentence context]. My goal is to [hold a boundary / decline politely / ask for what I need]. Tone: warm but firm, under 80 words, no apologies, no hedging. Here's their message: [paste]

Help me think through [decision]. The options I'm weighing are [list]. The constraints I have are [budget / time / who's involved]. What I care most about is [top 1-2 priorities]. Walk me through each option's strengths and weaknesses for MY situation specifically. Then tell me which one you'd pick and why — I want a real answer, not "it depends."

Use them as starting points, not finished products. Edit the bracketed bits, paste into ChatGPT or Claude, then iterate — the real magic is the back-and-forth. Last updated: May 2026.