This article is a little different from my usual “things I learned by doing” articles. I use AI for a lot of in-depth business and thinking work. We can spend hours working through a problem, comparing options, or figuring out what needs to change.
But some of my favorite uses take a few minutes and are generally random.
This week, I asked about a sweater, got help with a word game, and tried to understand why an image tool kept adding people I never asked for.
Here are five questions I asked AI this week and what came out of them.
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1. Sometimes I want another opinion.
I had a casual sundress, a sweater, and shoes picked out for a wedding. I couldn’t decide whether the sweater worked or made the whole thing look too formal.
Instead of texting someone a photo and waiting for an answer, I asked AI.
The prompt that started it:
“Does this sweater look OK with this sundress?” [insert two pictures]My life lesson:
This was a small decision. A second opinion was enough to help me make it.
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2. AI is perfectly acceptable for cheating at word games.
At one point this week, my biggest problem was staring at a pile of letters and failing to see the word hiding in them.
So I started feeding the letters to AI.
STATUS. MOONLIGHT. CLASSROOM. ARTICLE.
I won’t pretend this was productive. But it was useful at that exact moment.
The prompt that started it:
“Use these letters to spell a word, don't add or subtract any: asstut”My life lesson:
Next time you play Scrabble, sneak off and get a second opinion.
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3. Two weird failed orders can give you something to investigate.
A client had two failed orders come through her online store with strange names and even stranger notes.
My first thought was: Is someone testing stolen credit cards?
The prompt that started it:
“I just had two failed orders come through my cart… was it testing credit cards?”That question helped me investigate card testing, how bots use checkout forms, and what Stripe was already blocking. It also led me to check where Cloudflare Turnstile could add another layer of protection.
A random “what the hell is this?” became an actual fix.
My life lesson:
Ask about what you suspect. Then check whether the evidence supports it.
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4. Sometimes the problem with the picture isn’t your prompt.
I spent far too much time trying to get Midjourney to create a homepage image without putting people in it.
More specifically: men.
Tell it “no people.” There’s a man.
Try a different scene. Man.
Change the concept. Hello again, random man.
Eventually, I stopped asking for another image and asked about the problem itself.
The prompt that started it:
“Why does Midjourney put men in every f*cking picture, even if you tell it no people?”That led to a conversation about patterns in training data and why an image generator might keep adding something I didn’t want.
It also gave me a different approach to try: Describe a scene where a person has no reason to be.
My life lesson:
Sometimes a question and a cuss word help you stop repeating the same failed approach.
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5. “Can AI see this?” is becoming a more useful question.
I wanted to connect AI to Cloudways so I could ask questions about my servers. I was tired of digging through dashboards and trying to interpret everything myself.
The prompt that started it:
“Do you have an MCP for Cloudways servers?”That sent me into connection tools, access tokens, and permissions. Knowing about Cloudways is one thing. Having permission to inspect my account is another.
It also gave me a better question to ask: What information can I safely give AI access to so it can help me understand what’s happening?
My life lesson:
Before spending time collecting information by hand, ask whether AI can access the source and what permission it needs.
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None of these questions needed a sophisticated prompt. I asked the question that was in my head, then followed up when I needed more.
That’s an easy way to get more comfortable using AI. Ask about the small, weird, ordinary things that catch your attention.
Sometimes you get an answer. Sometimes you find a different question worth asking.
And sometimes you finally figure out what word you can make from asstut.