Hey there,
Welcome back. And a warm hello to anyone joining us for the first time.
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A quick note before we get going. When I say "side hustle or small business" today, I do not just mean people with a registered company and a storefront. I mean anyone selling something on Facebook Marketplace, running an Etsy shop on weekends, walking dogs after work, or doing a bit of freelance writing on the side. If you make even a little bit of money from something outside your day job, this one is for you.
And if that is not you at all, stick around anyway. A lot of what is below is just as useful for organizing a hobby, a fundraiser, or a community group you help run.
The part nobody tells you about running something small
Running a side hustle rarely fails because the idea was bad. It usually fails because the person behind it burns out doing the parts that have nothing to do with why they started. Writing listings. Answering the same three questions over and over. Trying to remember what they spent on supplies back in March.
AI will not build your business for you, and it will not replace the thing that actually makes people buy from you, which is you. But it can take a real bite out of the busywork. Here is how.
Four prompts to try this week
Prompt 1: Stress-test your idea before you spend a dollar Before you order supplies or set up a shop page, it is worth having something honestly poke holes in your plan. Tell AI what you are thinking of doing, and ask it to play devil's advocate. What would make this harder than expected? What are people in this space usually surprised by? This will not replace real research, but it is a genuinely useful gut check, and it costs you nothing but ten minutes. Denise in Saskatoon had been thinking about selling hand-poured candles at weekend markets. Before buying wax and jars, she asked ChatGPT to challenge her plan. It raised things she had not fully thought through, how much table fees at markets actually eat into margins, and how seasonal candle demand really is outside of the fall and winter months. She adjusted her pricing and picked her first three markets more carefully because of it. Fill in the blank:
Ready to use example:
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Prompt 2: Write a listing or service description that still sounds like you Staring at a blank listing page is one of the most common places people get stuck. Instead of asking AI to write the listing from nothing, give it the plain, unpolished facts the way you would tell a friend, then ask it to shape that into something clear and appealing. You keep the voice. AI just helps with the structure. Marcus in Victoria started walking dogs in his neighbourhood after retiring and wanted a simple post for the local community Facebook group. He gave AI the basics, his availability, that he had raised dogs his whole life, that he lived two blocks from the off-leash park, and asked it to turn that into a short, friendly post. He tweaked a couple of lines so it still sounded like him, and had three replies within the day. Fill in the blank:
Ready to use example:
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Prompt 3: Set up a simple way to track what you earn and spend A quick note before this one. Keep any real account numbers or banking details out of what you paste into AI, round figures are all you need here, and treat what AI tells you about taxes as a starting point, not final advice. When it comes to anything involving the CRA, a bookkeeper or accountant is worth the conversation, especially once real money starts moving. With that said, AI is genuinely useful for building a simple system from scratch if you do not have one yet. Ask it to set up a basic spreadsheet layout for tracking income and expenses for whatever you are doing, and to explain in plain terms what a sole proprietor in Canada generally needs to keep receipts for. Priya in Guelph had been selling beaded jewelry on Etsy for months and was tracking nothing beyond what was in her head. She asked ChatGPT to set up a simple spreadsheet layout for income and expenses and explain, in plain terms, what a hobby business like hers should generally be keeping receipts for. She built the sheet in an afternoon and finally had a real picture of whether she was actually making money. Fill in the blank:
Ready to use example:
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Prompt 4: Draft a reply to a tricky customer message Every side hustle eventually gets a message that is hard to answer calmly. A late order, a refund request, an unfair review. Instead of firing off a reply while you are still annoyed, paste the message into AI, explain the real situation, and ask for a calm, professional draft you can adjust before sending. It takes the edge off and almost always gets you a better outcome than the reply you would have sent in the moment. A reader in St. John's who sews custom baby blankets on the side got a message from a customer upset that an order arrived two days later than expected, even though the listing clearly stated a two to three week turnaround. She was frustrated but did not want to sound defensive. She asked Claude to help her draft a reply that acknowledged the customer's disappointment without apologizing for something outside her control. It struck exactly the tone she wanted, and the customer left a five star review a week later. Fill in the blank:
Ready to use example:
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Your challenge this week
If you already have something on the go, try Prompt 3 this week even if the idea of tracking your money makes you wince a little. It is the one people put off the longest and get the most relief from once it is actually done. If you are still just thinking about starting something, Prompt 1 is where to begin. Let AI find the holes before reality does.
Coming up next issue
Next issue is a more personal one. A real story about a time one of my own AI tools quietly started drifting off track without me noticing right away, what that looked like, and what it taught me about actually keeping an eye on the things AI builds for you.
AI assisted, Human led. Whatever AI produces for you, always read it, verify it, and make it sound like you. AI is an incredible first draft machine. Your judgment, your voice, and your values are always the final layer. |
As always, I read every reply personally. Do you have a side hustle on the go, or is there something you have been thinking about starting? Hit reply and tell me about it. I would love to hear what you are working on.
If you found this useful, pass it along to someone you know who sells, makes, or offers something on the side. This one might be exactly the nudge they need.
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Talk soon,
Chris
Founder, AI, Eh?