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May 21, 2026

Issue 21: Smarter by Thursday

Smarter by Thursday — Issue 21

Issue 21 · week of May 18, 2026

Smarter by Thursday

One practical AI win, every week. No jargon required.

By Dr. Rowan Hayes · Estimated read time: 6 minutes

If you’ve ever spent a Sunday afternoon trying to make a road trip feel “easy” or stared at a bad service experience and thought, “Someone needs to write a proper complaint about this,” this issue is for you. Today’s two topics are practical ones: using AI to plan a road trip and using AI to write a complaint letter that actually gets a response. Both matter because they save time, lower stress, and help you say what you mean without turning it into a second job.

Try at least one before Sunday. That is the whole assignment.

Use Case 1 of 2

Use Case 1: Planning a road trip using AI

On a Thursday evening in late May, Linda Alvarez, 58, is sitting at her kitchen table in Columbus, Ohio, with a half-empty mug of tea and three sticky notes that say “Mammoth Cave,” “avoid tolls,” and “not too much driving.” She and her husband want to drive to North Carolina in July, but every time she starts looking at routes, hotels, and stops, she gets buried in tabs. Which highways are better? Where should they stop the first night? What if the kids join for one leg? She doesn’t want a travel essay. She wants a sensible plan she can trust enough to start booking. That’s where AI can help, not by dreaming up a fantasy vacation, but by organizing the messy middle into something usable.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I’m planning a road trip and I want help making it practical, not fancy. Build me a realistic road trip plan using the details below.

Trip details: - Starting point: - Destination: - Date range: - Number of travelers: - Ages of travelers: - Vehicle type: - Driving comfort level: - Preferred driving limit per day: - Must-see stops: - Things to avoid: - Budget range: - Hotel preferences: - Food preferences: - Any mobility, sleep, or schedule needs:

What I want from you: 1. Suggest the best route options and explain why each one makes sense. 2. Recommend where to stop each day if I want to keep driving days reasonable. 3. Suggest 2 - 3 good overnight towns or cities for each stop. 4. Include likely drive times, but tell me where traffic or weather could change them. 5. Give me a simple, step-by-step trip plan I can use to book hotels and start packing. 6. If anything I forgot to think about, list it at the end.

Do not make this overly dreamy or vague. Be specific, practical, and honest. If you are unsure about something, say so clearly instead of guessing.

Why this prompt works: It gives AI the facts it actually needs instead of saying “plan my trip” and hoping for magic. Good prompts for travel include the starting point, destination, dates, and your real limits, like how many hours you want to drive in a day. That lets the model produce something grounded: route choices, overnight stops, and tradeoffs. The instruction to be practical also helps keep it from wandering into postcard language.

One thing to watch out for AI can be confident about roads, drive times, or hotel suggestions and still be wrong or outdated. It may also miss seasonal problems like construction, holiday traffic, or mountain weather. Use it to organize your thinking, then verify route details and booking options yourself before you spend money.

Use Case 2 of 2

Use Case 2: Writing a complaint letter that actually gets results

On a Monday morning at 9:15, Gerald Thomas, 66, is sitting in his home office in Dayton with a bill from his internet provider and a long memory of bad customer service. The company overcharged him for three months, then bounced him between two support agents who each promised it would be fixed “within 24 hours.” Gerald is not trying to start a war. He just wants the charges reversed and a clear apology. But he knows from experience that angry, rambling complaints usually get ignored. AI can help him write something calm, firm, and effective - something that sounds like a person who expects action, not drama.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

Help me write a complaint letter that is firm, polite, and likely to get results.

Situation: - Company or organization: - What happened: - Dates or timeline: - What I paid or lost: - What I already tried: - Who I spoke to, if anyone: - My account number or order number: - What outcome I want:

Write the letter so it: 1. Briefly explains the problem in plain language. 2. Shows that I’ve already tried to resolve it. 3. Clearly asks for the specific result I want. 4. Stays calm and professional, not angry or sarcastic. 5. Sounds like a real person, not a legal document.

Also give me: - A stronger version if the first draft is too soft - A shorter version I could paste into an email or web form - A subject line that sounds serious but not dramatic

Do not invent facts. If my details are missing, tell me what I need to add before drafting the final version.

Why this prompt works: Complaint letters succeed when they are specific, brief, and easy to act on. This prompt forces AI to ask for the facts that matter: what happened, when, what was lost, and what resolution is being requested. It also keeps the tone from drifting into either apology or rage. Good prompts like this tell AI the job is not “write something impressive.” The job is “write something that gets read by a tired customer service person.”

One thing to watch out for AI may make the letter sound smoother than you actually are, which is useful up to a point. But if it adds facts, legal threats, or emotional language you didn’t intend, that can weaken your case. Check every detail carefully, and if the issue could become legal or financial, keep your own records and consider getting human advice before sending.

Know someone who spends too long on things AI could do in two minutes?

Forward Smarter by Thursday to three people who subscribe and I will send you my free AI Prompt Starter Pack: 20 ready-to-use prompts for everyday life.

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Smarter by Thursday · By Dr. Rowan Hayes · drrowanhayes.com
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