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July 20, 2026

Issue 29: Smarter by Thursday

Smarter by Thursday — Issue 29

Issue 29 · week of July 20, 2026

Smarter by Thursday

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

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

Two things matter more than they look this week: planning a road trip without turning it into a moving stress test, and writing a complaint letter that actually gets a human being to take you seriously. AI can help with both, but only if you give it the right kind of instructions and then check its work.

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 July, Ellen, 58, is sitting at her kitchen table in Columbus with a legal pad, a half-finished cup of coffee, and a plan to drive to Santa Fe with her sister in September. She has the broad outline: two weeks, not too much driving each day, decent hotels, scenic stops, and absolutely no days that end with “we drove eight hours and then argued in a parking lot about dinner.” What she does not have is the part that usually eats the whole afternoon: figuring out the route, the pacing, and the places worth stopping without missing the trip she actually wants to have. That is where AI can help, but only if Ellen treats it like a planning partner, not a fortune teller.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I am planning a road trip and want help building a realistic itinerary. Ask me any clarifying questions first before you suggest anything.

Here are my basics: - Start: Columbus, Ohio - Destination: Santa Fe, New Mexico - Travelers: 2 adults, ages 58 and 61 - Dates: mid-September - Total trip length: 12 to 14 days - Maximum driving time per day: 5 to 6 hours - Budget: mid-range hotels, good value, not luxury - Interests: scenic drives, small towns, good food, interesting museums, and places with easy walking - Avoid: overly touristy stops, packed schedules, and long detours that do not add much

Please give me: 1. Three route options with different trade-offs 2. A day-by-day itinerary for the best option 3. Suggested overnight stops 4. A rough daily driving estimate 5. Places that are worth the detour and places I should skip 6. Backup options if weather, road work, or fatigue changes the plan

Do not book anything. Do not assume I want to drive more than I said. If a day looks too full, simplify it. If a stop is not a good fit for adults in their late 50s, say so directly.

Why this prompt works: It gives the AI the kind of input it can actually use: where you are starting, where you are going, how long you have, what matters to you, and what to avoid. It also asks for trade-offs instead of one “perfect” answer, which is important because road trips are always a compromise between distance, scenery, rest, and curiosity. The last part matters too: telling the AI not to overfill the day makes it more likely to produce something a normal person can live with.

One thing to watch out for AI travel plans can look polished and still be wrong in practical ways. A route may sound lovely but involve too much zigzagging, unrealistic arrival times, or attractions that are closed on the day you arrive. Treat the first draft as a sketch, then verify road conditions, hours, and hotel details separately before you commit.

Use Case 2 of 2

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

On a Friday afternoon, Marcus, 66, has one of those maddening problems that never feels big enough to hire a lawyer over but is absolutely big enough to ruin his week: a hotel charged him twice for the same stay, customer service has bounced him between departments, and the latest email he received begins with “We appreciate your patience,” which is corporate code for “please go away.” He does not need a rant. He needs a letter that is calm, specific, and hard to dismiss. AI is useful here because it can turn anger into structure, which is often the difference between being ignored and being refunded.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I need help writing a complaint letter that gets results.

First, ask me for the facts you need. Then draft a short, firm letter in plain language that I can send to a company.

Here is the situation: - Company: [name] - Problem: [what happened] - Date(s): [dates] - Amount involved: [$ amount] - What I already did: [calls, emails, chats, case numbers] - What I want: [refund, replacement, correction, apology, written confirmation] - Tone: polite, firm, not emotional, not threatening - Length: one page or less

Please make the letter include: - A clear subject line - A simple timeline of what happened - The specific outcome I want - A deadline for response - A final sentence that says I will escalate if needed, without sounding dramatic

Then give me: 1. A stronger version for customer service 2. A version for a manager or executive 3. A list of details I should attach as evidence

Do not make it sound legalistic. Do not overdo the emotion. Do not use fancy words when simple ones work better.

Why this prompt works: Good complaint letters are not about sounding outraged; they are about being easy to understand and difficult to ignore. This prompt tells the AI to gather the facts first, which is important because missing dates, amounts, and prior contacts are exactly what weaken most complaints. It also forces the letter to stay short, specific, and action-oriented, which is what busy customer service people respond to most often.

One thing to watch out for AI can make a complaint sound smoother than it should, and that is not always an advantage. If the letter becomes too polished, it may blur the timeline or include claims you cannot prove. Read every sentence carefully, especially the dates, numbers, and the exact remedy you want, because those are the parts that matter if the company actually takes you seriously.

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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