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July 16, 2026

Issue 29: Smarter by Thursday

Smarter by Thursday — Issue 29

Issue 29 · week of July 13, 2026

Smarter by Thursday

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

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

If you have ever stared at a blank screen thinking, *I just want this road trip planned without turning it into a second job*, or *I want this complaint letter to do more than sound annoyed*, this issue is for you. AI can help with both tasks, but only if you give it the kind of direction a busy, capable person would give a good assistant. Road trips need constraints, not fantasy. Complaint letters need facts, not fury.

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 Tuesday afternoon in late June, Janet, 62, sits at her kitchen table in Columbus with a yellow notepad, a half-finished cup of coffee, and two weeks before she and her husband leave for a road trip to Santa Fe. She wants scenic drives, good lunches, and no exhausting nine-hour days behind the wheel. Her daughter tells her to “just ask AI,” so she does. The first version gives her a cheerful but useless itinerary that ignores her dislike of long driving days, suggests a few stops that are miles out of the way, and forgets that they hate checking into hotels after dark. This is exactly where AI can help, but only if Janet treats it like a planning partner with a strong memory for instructions and no native sense of common sense.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I am planning a road trip and I want you to help me build a realistic, enjoyable itinerary.

Trip details: - Starting point: - Ending point: - Travel dates: - Number of travelers: - Ages, if relevant: - Maximum driving time per day: - Total budget: - Hotel style I want: - Things we care about: - Things we do not want: - Mobility, food, or timing limits: - Any must-see stops:

Please do three things: 1. Suggest the best route with a day-by-day plan. 2. Keep the driving days reasonable and group stops by area so we are not zigzagging all over the map. 3. Include one backup option for bad weather, traffic, or a sold-out attraction.

Before you start, ask me up to five questions if anything important is missing. When you answer, explain the trade-offs clearly and tell me which parts I should verify before booking.

Why this prompt works: It gives AI the same kind of structure a human travel agent would need: where you are starting, where you are going, how long you want to drive, what kind of trip you actually enjoy, and what you do not want. Microsoft’s Copilot guidance recommends sharing dates, destinations, interests, then refining with follow-up prompts, while other travel guides emphasize that the more specific the constraints, the better the itinerary. Asking for backup plans also matters because AI trip ideas can look good on paper while failing in real life.

One thing to watch out for AI can invent details that sound plausible but are wrong, especially for hotel names, opening hours, road closures, and driving times. Treat the itinerary as a first draft, not a reservation confirmation. Before you commit, verify any critical detail with maps, official websites, or current traffic and weather information.

Use Case 2 of 2

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

On a Thursday morning at 8:15, Leonard, 58, opens the bill from his internet provider and sees the same problem for the third month in a row: a charge he was told had been removed. He is angry, but he also knows that a rant gets ignored and a clean, specific complaint sometimes gets action. He does not want a “Dear Sir or Madam” letter that sounds like it was written by a machine. He wants something firm, organized, and impossible to dismiss. This is where AI can help if you feed it the facts, the outcome you want, and the tone you need.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I need help writing a complaint letter that is firm, clear, and professional.

Here are the facts: - Company name: - What happened: - Dates and times: - Account number or reference number: - What I was promised or told: - What the problem cost me: - What I already tried: - The result I want: - Deadline, if any:

Write a complaint letter that does all of the following: - States the problem clearly in the first paragraph - Explains the facts in a simple timeline - Names the specific result I want - Uses a calm but firm tone - Sounds like a real person, not a legal memo - Leaves out threats, insults, and extra drama

After the letter, give me a shorter version I can use as an email subject line and opening paragraph.

Why this prompt works: Complaint letters succeed when they are specific, organized, and outcome-driven. AI is useful here because it can turn messy frustration into a clean timeline and keep the tone steady, which matters when the goal is to be taken seriously. Good prompts also tell the model what *not* to do: no threats, no rambling, no emotional overstatement. That improves the odds that the letter reads like evidence rather than venting.

One thing to watch out for AI can make your complaint sound stronger than the facts actually support, which is a mistake. If it adds claims you cannot prove, the letter becomes easier to ignore. Also, if you give it vague complaints like “they were rude” without dates, names, or documents, the result will be generic and weak. The best complaint letters are built from specifics, not adjectives.

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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