Real small business challenges, fixed with AI (before & after) 🐾
An Etsy seller, a consultant, and a nonprofit director — three business challenges, three AI conversations, three very different outcomes.
This week I’ve been hearing from readers who run small businesses — and the challenges coming in are so specific and so real that I want to spend today’s post on three of them.
Each one is a situation that came up in the community this week. Each one has a before — what the person was stuck on — and an after — how an AI conversation helped them move through it.
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Linda, 64 — Etsy shop owner, handmade candles
“My product descriptions have always felt flat to me. I know what makes my candles special — the story behind them, the way they smell, the feeling they give — but when I try to write it down it comes out generic. I used the marketing copy prompt and told AI the story behind my best-selling candle. What came back captured it better than anything I’d written in three years.”
Linda’s key move: she gave AI the story, not just the product specs. “This candle smells like Sunday morning in my grandmother’s kitchen” is marketing. “Vanilla and cinnamon soy wax” is a label. AI can work with a story. It can’t invent one for you.
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Richard, 69 — Independent HR consultant
“I’ve been doing consulting for twelve years and I’ve never once raised my rates. I know I should — my clients tell me constantly that I undercharge. But every time I think about it I freeze. I used the pricing assumption prompt and the question ‘What would I need to believe about my work to feel comfortable charging more?’ stopped me completely. I sat with it for two days. Then I sent three clients a rate increase email that AI helped me draft. All three said yes without a word.”
Richard’s key move: he didn’t ask AI what to charge. He asked AI to help him examine why he was afraid to charge it. That’s a different conversation — and a more useful one.
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Patricia, 71 — Nonprofit director, local literacy program
“I needed to write a grant application letter and I was dreading it. I’m good at running the program. I’m not good at making it sound impressive on paper without it feeling like I’m bragging. I told AI what our program does, who we serve, what we’ve achieved, and asked it to write something that leads with the impact on real people, not statistics. The letter it drafted made me cry a little. We submitted it last week.”
Patricia’s key move: she told AI what she was bad at (making herself sound impressive) and what she wanted instead (impact over statistics). Being specific about the problem gets you a specific solution.
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Send me your business challenge
If you’re running something — any size, any kind — and there’s a specific task that’s been taking too long, costing you sleep, or just sitting on your list week after week: hit reply and describe it. Be specific. What is the task, what have you tried, and what’s making it hard? I’ll feature the best scenarios in a future Wednesday post and show you exactly which prompt to use.
📅 Catch up on this week:
🎬 Sunday: How I Use AI to Run My Small Business (The Parts Nobody Shows You)
🎬 Tuesday: The 15-Minute Weekly AI Workflow for Small Business
Come back Thursday for the lecture — I’m going strategic. Positioning, pricing psychology, bottleneck diagnosis, and your 90-day plan. The biggest lesson of the week.
Hit reply. Tell me your challenge. 🐾
— Debbie
AI Puppy Playbook