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Hey there,
Welcome back. And a warm hello to anyone joining us for the first time. Really glad you are here.
The sunburn has faded. The inbox has cleared up. Slightly. And I am back with what was supposed to be one issue about ChatGPT and turned into two, because ChatGPT has been busy and there is genuinely too much to cover in a single email without making your eyes glaze over.
So here is the updated plan. Issue 9 (this one) is a proper look at what ChatGPT can actually do right now, including some things that have changed significantly in the last year that most people have no idea about. Issue 10 will be a dedicated deep dive into ChatGPT's image creation, because that topic alone deserves its own issue. And after that we will be digging into AI and Canadian privacy law, plus a lot more to come beyond that.
Quick recap of where we have been:
Right. Let's talk about ChatGPT.
Your mental model of ChatGPT is probably out of date
Most people's picture of ChatGPT is the version that launched in late 2022. You typed something in, it typed something back. Sometimes it was great. Sometimes it was confidently wrong. It felt like a novelty.
That version of ChatGPT is long gone. What exists now is genuinely different. It can remember things about you across conversations. It can search the web in real time. It can generate and edit images. It can reason through complex problems step by step. And it is available, at least in its most useful form, for free.
If you tried it once a year or two ago and moved on, or if you are using it the same way you always have, this issue is going to change how you think about it.
Four things ChatGPT can do right now that most people are not using
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1. Brainstorming and getting unstuck
This is where ChatGPT genuinely shines. When you are staring at a blank page, a blank calendar, or a problem you cannot quite see your way around, it is an exceptional thinking partner. Not because it does the thinking for you, but because it gives you options you would not have come up with on your own, quickly, without judgment, and as many as you need.
Marcus in Winnipeg was trying to figure out how to talk to his teenage son about choosing a college program. He had no idea how to start the conversation without it turning into an argument. He described the situation to ChatGPT and asked for a few different ways he could approach it. He got five options, ranging from low-key and casual to more structured. He picked one, tweaked the wording to sound like himself, and had the conversation that weekend. It went fine.
Fill in the blank prompt:
| "I am trying to [DESCRIBE THE SITUATION OR DECISION]. I am not sure how to approach it. Give me [NUMBER] different options or angles I could consider, and for each one, give me a sentence on the pros and cons." |
Ready to use example:
| "I am trying to figure out how to bring up the topic of retirement planning with my parents, who are in their late 60s and I do not think have much saved. It is a sensitive topic and I do not want to come across as prying or condescending. Give me four different ways I could approach this conversation and for each one, give me a sentence on the pros and cons." |
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2. Memory across conversations
This one surprises people. ChatGPT can now remember things you have told it in past conversations and carry that context forward. You can tell it your name, your situation, your preferences, and it will use that information the next time you open a new chat. You do not have to re-explain yourself every time.
You can also tell it things you want it to always keep in mind. Things like "I am a nurse in Nova Scotia and I work rotating shifts" or "I have two kids under five and a very limited budget for activities." That context makes every future conversation more useful, because it is no longer starting from zero.
To set this up, go to Settings, then Personalization, and make sure Memory is turned on. You can also just tell it things directly in conversation and it will save them automatically.
Fill in the blank prompt:
| "I want you to remember a few things about me so our conversations are more useful. [YOUR NAME]. I live in [YOUR CITY], Canada. I work as [YOUR JOB OR SITUATION]. My main priorities right now are [1-2 THINGS]. Please keep this in mind going forward." |
Ready to use example:
| "I want you to remember a few things about me so our conversations are more useful. My name is Sandra. I live in Red Deer, Alberta. I am a part-time bookkeeper and a full-time mom of three. My main priorities right now are saving money on groceries and finding activities for the kids that do not cost a fortune. Please keep this in mind going forward." |
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3. Searching the web in real time
One of the biggest criticisms of early ChatGPT was that its knowledge had a cutoff date. Ask it about something that happened recently and it would either not know or, worse, make something up. That problem is largely solved now.
ChatGPT can now search the web when it needs to. Ask it about current events, recent news, today's weather, or anything time-sensitive, and it will pull live information rather than guessing from what it already knows. It will even show you the sources it pulled from so you can verify things yourself.
This makes it genuinely useful for things like researching a product before you buy, checking what grants or rebates might be available in your province, or getting a quick summary of something in the news that you want to understand better.
Fill in the blank prompt:
| "Search the web and give me a plain English summary of [TOPIC]. I am based in [YOUR PROVINCE], Canada. I want to understand [WHAT YOU ARE TRYING TO LEARN]. Keep it simple and point me to any sources worth reading." |
Ready to use example:
| "Search the web and give me a plain English summary of what home energy rebates are currently available in Ontario, Canada. I own a house and I am thinking about upgrading my insulation and replacing my furnace. I want to understand what money might be available to help with the cost. Keep it simple and point me to any government sources worth reading." |
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4. Working through a decision step by step
This is one of my favourite uses of ChatGPT and one of the most underrated. When you have a genuinely difficult decision in front of you, one with a lot of moving parts and no obvious right answer, ChatGPT is surprisingly good at helping you think it through in a structured way.
You are not outsourcing the decision. You are using it the same way you might talk something through with a smart friend over coffee. Someone who listens, asks good questions, and helps you see the angles you might have missed. The final call is still yours. That is the point.
Priya in Vancouver was trying to decide whether to leave her stable government job to go back to school full-time. She had been going back and forth on it for months. She laid out all the details for ChatGPT, her financial situation, her family commitments, what she was hoping to get out of the degree, and asked it to help her think it through. It did not tell her what to do. It helped her see the decision more clearly, which was exactly what she needed.
Fill in the blank prompt:
| "I have a decision to make and I want help thinking it through. Here is the situation: [DESCRIBE IT]. The main things pulling me in different directions are [YOUR CONCERNS OR COMPETING PRIORITIES]. I am not looking for you to tell me what to do. I want you to help me think through the tradeoffs clearly and maybe ask me a few questions that will help me get more clarity." |
Ready to use example:
| "I have a decision to make and I want help thinking it through. I am 44 years old and considering leaving my stable government job in Calgary to take a contract position that pays significantly more but comes with no benefits and no job security. My mortgage is paid off and my kids are almost done high school, so my fixed costs are going down. The main things pulling me in different directions are the security of what I have versus the income and challenge of the new opportunity. I am not looking for you to tell me what to do. I want you to help me think through the tradeoffs clearly and maybe ask me a few questions that will help me get more clarity." |
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A note on the free version vs paid
The free version of ChatGPT is genuinely useful and a perfectly fine place to start. Memory and web search are both available on the free plan. The paid plan (ChatGPT Plus, currently around $28 CAD per month) gives you access to the most advanced models, higher usage limits, and priority access when the service is busy.
My honest advice: start with free. Use it for a few weeks and see whether you are running into limits. If you are, that is a good sign that it is actually working for you, and that is when it might be worth upgrading.
Your challenge this week
Pick one decision or situation that has been sitting in the back of your mind and spend ten minutes with ChatGPT on it. Describe the situation honestly, tell it what is making the decision hard, and ask it to help you think it through. You might be surprised how quickly things become clearer when you actually write them out and have something useful to respond to.
Coming up next
Issue 10 is all about ChatGPT's image creation. This feature has come a long way in the last year and most people have no idea what it is actually capable of now. We are going to walk through what it can do, when it is genuinely useful, and how to get results that do not look like they came from a robot. Worth your time.
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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.
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As always, I read every reply personally. Have you tried any of these with ChatGPT? Hit reply and let me know how it went. I genuinely want to hear what you tried and what surprised you.
If you found this useful, pass it along to someone who would get something out of it. The more Canadians who feel confident with this stuff, the better.
And one more thing. If you are interested in leadership, people management, or just navigating work with a bit more empathy and less chaos, I wrote a book about that. It is called The Human Side of Leadership and it is available on Amazon. You can find out more about it, and a bit more about me, at chrismackinnon.ca. No pressure, just putting it out there.
Talk soon,
Chris
Founder, AI, Eh?
theaieh.ca 🍁
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