Smarter by Thursday

Smarter by Thursday

Archives
Log in
Subscribe
October 14, 2026

Issue 41: Smarter by Thursday

Smarter by Thursday — Issue 41

Issue 41 · week of October 12, 2026

Smarter by Thursday

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

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

Intro paragraph 1: Two ordinary problems can become much easier with AI: planning a road trip you will actually enjoy, and writing a complaint letter that gets a useful response instead of disappearing into a customer-service inbox. Neither requires technical skill. You simply need to give AI enough real-world detail to work with - and enough boundaries to keep it from inventing a plan that looks good on paper but fails in practice.

Intro paragraph 2: 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

At 7:40 p.m. on Tuesday, October 13, Linda Morales sat at her kitchen table with three browser tabs open, a yellow legal pad beside her, and no clear idea how to get from Cleveland to Asheville without spending nine exhausting hours behind the wheel. She and her sister planned to leave the following Friday. Linda wanted scenic stops, a comfortable hotel, and time to walk around small towns - not merely the fastest route suggested by a map app. She also needed to avoid mountain driving after dark and keep the total cost reasonable. The problem was not finding information. It was sorting through too much of it. AI could help her create a first draft of the trip, provided she treated that draft as a planning assistant’s recommendation, not a final booking.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

> I am planning a road trip and want a realistic, comfortable itinerary - not the most aggressive driving schedule. > > Trip details: > - Starting point: Cleveland, Ohio > - Destination: Asheville, North Carolina > - Departure date: Friday, October 23, 2026 > - Return date: Tuesday, October 27, 2026 > - Travelers: Two adults, both in their 60s > - Vehicle: Personal car > - Maximum comfortable driving time: 5 hours per day, excluding stops > - Preferences: Scenic roads where practical, historic towns, easy walks, good local food, clean quiet hotels, and no driving on mountain roads after dark > - Avoid: Very strenuous hikes, large theme parks, crowded nightlife, and unnecessary backtracking > - Budget: About $225 per day for lodging, meals, fuel, and activities, excluding souvenirs > - We would like to spend two nights in one location rather than changing hotels every night. > > Create a day-by-day itinerary. For each day, include: > 1. Approximate driving time and mileage > 2. Two or three worthwhile stops > 3. A suggested lunch or dinner location > 4. A realistic arrival time > 5. One backup option in case of rain > 6. An estimated daily cost > > Put safety and comfort ahead of squeezing in more attractions. Identify any parts of the route that may involve difficult driving, seasonal weather, limited cell service, or a risk of arriving after dark. Do not invent opening hours, current prices, road closures, or hotel availability. Mark anything that must be checked before booking, and finish with a short checklist of what I should verify using official websites.

Why this prompt works: It gives AI the information a travel agent would need: dates, travelers, driving limits, budget, preferences, and things to avoid. The phrase “comfortable, not aggressive” changes the entire answer; without it, AI may optimize for distance and produce a punishing schedule. Asking for mileage, arrival times, costs, rain alternatives, and items to verify forces the response into practical details. Most importantly, the prompt tells AI not to invent current information. That matters because travel details change. AAA recommends realistic daily mileage, regular stops, emergency supplies, and a paper map or offline backup when planning a road trip.

One thing to watch out for AI may confidently recommend a restaurant, hotel, attraction, or road that is closed, fully booked, seasonal, or more expensive than the estimate. Check dates, opening hours, weather, road conditions, and reservations on official sources before leaving. Also remember that a computer cannot judge your fatigue, eyesight, comfort with winding roads, or the condition of your actual vehicle.

Use Case 2 of 2

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

On Wednesday, October 14, at 10:15 a.m., Robert Chen opened his latest internet bill and discovered that a promised $60 monthly discount had vanished. He had already spent forty minutes on the phone two weeks earlier. The representative had said the problem was corrected, but the next bill showed an additional $118 in unexplained charges. Robert was angry, which was understandable, but his first draft was mostly anger: “Your company has lied to me repeatedly, and I am done being treated like an idiot.” That may express the truth of his frustration, but it gives the company little to act on. A strong complaint letter is calmer and more specific. It identifies the agreement, the error, the evidence, the remedy requested, and the deadline for responding.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

> Help me write a firm, concise complaint letter to my internet provider. > > My goal is to have the billing error corrected, the promised discount restored, and any improper fees removed. Do not make threats, exaggerate, or use insulting language. > > Facts: > - Company: [company name] > - My name: [full name] > - Account number: [account number] > - Service address: [address] > - Date I signed up or changed service: [date] > - Promise or offer made: [describe the price, discount, or terms] > - What my bill should have shown: [amount] > - What the bill actually shows: [amount] > - Amount I dispute: [amount] > - Dates and short summaries of previous conversations: [list them] > - Names or employee numbers of representatives, if known: [details] > - Documents I can attach: [contract, email, screenshots, bills, notes] > > Write a letter of no more than 450 words. Include: > 1. A clear subject line > 2. A brief timeline of what happened > 3. The exact amount disputed > 4. The specific correction I am requesting > 5. A request for a written response within 14 calendar days > 6. A sentence stating that I am keeping copies of the letter and supporting documents > 7. A professional closing > > Do not invent facts, legal rights, deadlines, or company policies. If any important information is missing, put [ADD DETAIL HERE] rather than guessing. After the letter, provide a short list of documents I should attach and a separate list of statements I should verify before sending.

Why this prompt works: The prompt separates facts from feelings and tells AI exactly what outcome to request. It also supplies a structure: timeline, disputed amount, remedy, deadline, and evidence. The instruction to use “[ADD DETAIL HERE]” is essential because AI often fills gaps with plausible but untrue details. A firm tone works better than an insulting one because the letter can be forwarded to a supervisor, regulator, or dispute department without weakening your credibility. The FTC recommends including relevant information, keeping a copy, and considering certified mail with a return receipt for important complaints.

One thing to watch out for A polished letter is not proof that your position is legally correct. Check the contract, billing records, warranty, and applicable deadline yourself, and do not claim that a company violated a law unless you have verified it. Send the complaint to the correct department, preserve your evidence, and escalate through the appropriate regulator or dispute process if the company does not respond.

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 42: Smarter by Thursday Older → Issue 41: Smarter by Thursday
Bluesky
Powered by Buttondown, the easiest way to start and grow your newsletter.