Smarter by Thursday logo

Smarter by Thursday

Archives
Log in
Subscribe
June 22, 2026

Issue 25: Smarter by Thursday

Smarter by Thursday — Issue 25

Issue 25 · week of June 22, 2026

Smarter by Thursday

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

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

Two jobs people keep handing to AI this summer are *trip planning* and *complaint writing*. Both sound simple until you are the one juggling dates, budgets, bad roads, bad service, and the very human problem of wanting something fixed without sounding angry or foolish.

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 morning in late June, Linda, 58, in Columbus, opens her laptop with three sticky notes beside it: one says “Denver with sister,” one says “avoid exhausting drive days,” and one says “don’t miss anything good.” She is not trying to become a travel expert. She just wants a road trip that feels manageable instead of messy. AI can help with that, but only if she gives it the kind of details a real person would use when talking to a practical friend. Microsoft’s Copilot recommends sharing dates, destinations, interests, and preferences, then refining the plan with follow-up prompts, and Outside found that more specific travel questions produce more robust itineraries.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

```text Help me plan a road trip like a sensible travel assistant, not a fantasy travel influencer.

Trip details: - Starting point: [your city] - Destination: [destination] - Dates: [dates] - Number of travelers: [number] - Ages or mobility issues, if relevant: [details] - Driving style: [fastest / most scenic / balanced] - Daily driving limit: [hours or miles] - Budget level: [low / moderate / comfortable] - Interests: [food, history, nature, quiet towns, museums, scenic drives, family activities, etc.] - Things we want to avoid: [long detours, expensive attractions, crowded tourist traps, toll roads, night driving, etc.]

What I want from you: 1. Give me 2 route options: fastest and most scenic. 2. Build a day-by-day driving plan with realistic drive times and rest stops. 3. Suggest good places for lunch, bathrooms, coffee, and an overnight stop each day. 4. Cluster activities by geography so we are not zigzagging all over the map. 5. Include backup options in case of rain, traffic, or a closed attraction. 6. Flag anything that should be verified before we leave, such as road closures, weather, or reservation requirements. 7. Keep the tone practical and specific.

Before you finalize anything, ask me up to 5 questions that would help improve the plan. ```

Why this prompt works: It gives the AI the same facts a good travel planner would need, especially constraints, preferences, and non-negotiables. Microsoft’s guidance stresses clear prompts, follow-up refinement, and verifying critical information, while Seven Corners notes that rephrasing or recreating parts of the itinerary can improve weak results. The request for route options, grouped stops, and backup plans pushes the AI beyond a generic list of attractions and into something usable.

One thing to watch out for AI trip plans can look polished while still being unrealistic, and Outside notes that the first pass is often more of an outline than a finished itinerary. The weak spot is usually the human stuff: too much driving, not enough downtime, or a “scenic stop” that turns out to be a ten-minute overlook with no bathrooms. Always check hours, reservations, weather, and road conditions before you leave.

Use Case 2 of 2

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

On a Friday afternoon, George, 67, in Phoenix, is staring at a hotel bill that includes a “resort fee” he never agreed to, plus a charged minibar item he did not touch. He is not looking for a legal battle. He wants the bill corrected quickly, politely, and without writing a letter so angry that it gets ignored. AI can help him draft a firm complaint letter, but only if he gives it the facts, the outcome he wants, and the tone he wants the company to feel when they read it. That matters because most complaint letters fail for one of two reasons: they are too vague to act on, or so emotional that they stop sounding credible.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

```text Write a complaint letter that is firm, specific, and likely to get a helpful response.

Use these details: - My name: [name] - Company or organization: [name] - What happened: [clear summary in 3-5 sentences] - Date(s): [dates] - Account number, invoice number, order number, or reservation number: [details] - Amount involved: [amount] - What I have already done: [calls, emails, chats, screenshots, receipts, prior case numbers] - What I want fixed: [refund, replacement, correction, apology, fee removed, account corrected, etc.] - Deadline: [reasonable date] - Tone: calm, professional, and firm

Write: 1. A subject line. 2. A short opening that states the problem plainly. 3. A middle section with the facts in chronological order. 4. A clear request for the exact remedy I want. 5. A final paragraph that says I am willing to resolve this quickly.

Keep it under 300 words. Do not be rude. Do not sound legalistic. Do not exaggerate. Do not add facts I did not provide.

After the letter, give me 3 stronger subject lines and 3 shorter versions I could use in an email or online complaint form. ```

Why this prompt works: Good complaint letters are not dramatic; they are easy to process. This prompt forces the AI to stick to facts, chronology, and a single desired outcome, which is what customer service teams can actually act on. It also helps the AI avoid the two classic mistakes: overexplaining the story or writing something so soft that nobody feels responsible for responding. A concise letter with dates, reference numbers, and a specific remedy is much more useful than a long emotional paragraph.

One thing to watch out for AI can make a weak case sound polished, but polish is not evidence. If you do not provide receipts, dates, names, and prior contact history, the letter may sound convincing while still being easy to dismiss. Also, some companies respond better to a short, plain complaint than to a formal-sounding one, so if the first version gets ignored, ask the AI to rewrite it in simpler language with fewer adjectives and more concrete facts.

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.

Forward by email Open in browser Share on Facebook
Smarter by Thursday · By Dr. Rowan Hayes · drrowanhayes.com
Unsubscribe · View in browser

Don't miss what's next. Subscribe to Smarter by Thursday:
← Newer Issue 25: Smarter by Thursday Older → Issue 25: Smarter by Thursday
Bluesky
Powered by Buttondown, the easiest way to start and grow your newsletter.