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June 20, 2026

Issue 25: Smarter by Thursday

Smarter by Thursday — Issue 25

Issue 25 · week of June 15, 2026

Smarter by Thursday

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

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

Aiden spent last Saturday night staring at a map, three browser tabs, and a half-finished road trip plan for his family’s July drive from Cleveland to Asheville. Meanwhile, Marcy was trying to write a complaint letter about a broken refrigerator that had been “scheduled” for repair three times and never fixed. These are the two kinds of jobs AI can actually help with: planning something complicated, and saying something firmly without sounding angry or confused.

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 Tuesday at 7:40 p.m., Aiden, 58, is at the kitchen table with his wife and two grandchildren asking the same question every family faces before a long drive: “Where should we stop so this does not turn into a miserable day?” He has the route, but not the shape of the trip. He wants rest stops that feel safe, a lunch stop that is not a fast-food gamble, a place to stretch the kids’ legs, and maybe one scenic detour if it does not add two hours and a fight. The problem is not that Aiden lacks information. The problem is that road-trip planning requires sorting too many small choices at once. AI can help by turning a pile of preferences into a usable plan, but only if you tell it the trip in plain language and make it do the organizing work for you.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

You are my road trip planner. Help me plan a comfortable, realistic road trip for a [number]-hour drive from [starting city] to [destination city] on [date or day of week]. I am traveling with [who is traveling with me, including ages if relevant]. My priorities are: [comfort / speed / scenic views / kid-friendly stops / avoiding tolls / avoiding steep hills / avoiding night driving]. Please give me a plan with: 1. The best route option in plain English 2. Two or three good places to stop for coffee, lunch, and bathrooms 3. One optional scenic or interesting stop if it does not add more than [x] minutes 4. A suggested schedule with approximate times 5. Things I should avoid or be careful about on this route Please keep the advice practical, not fancy. If you are unsure about a place, say so instead of guessing. If there are multiple good options, give me the top two and explain the difference.

Why this prompt works: It gives the AI the job, the route, the people, and the priorities, which is what turns a vague request into a useful plan. It also asks for a schedule, not just suggestions, because a road trip falls apart when you know where to go but not when to leave each place. The instruction to “say so instead of guessing” matters because AI can sound confident about places it has not actually verified.

One thing to watch out for AI is best used as a planner, not as a live map. It may recommend a restaurant that has closed, a scenic stop that no longer fits your timeline, or a route that looks good on paper but is bad in traffic. Before you leave, check the final stops against current hours, road conditions, and your navigation app. That extra five minutes is what keeps a good plan from turning into a story about missed exits.

Use Case 2 of 2

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

On Thursday morning at 9:15, Marcy, 64, opens her email for the fourth time and sees the same useless message from an appliance company: “Your case is being reviewed.” Her refrigerator has been broken for two weeks, her groceries are ruined, and she is past the point of polite disappointment. She does not want a rant. She wants action. This is exactly the kind of moment where AI can help, because the strongest complaint letters are not emotional. They are specific, organized, and hard to ignore. The trick is to give AI the facts, the outcome you want, and the tone you want to project: calm, firm, and serious.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

Write a complaint letter on my behalf to [company name]. The problem is: [brief description of the issue]. Here are the facts in order: - [date and first problem] - [what I tried] - [dates of follow-up] - [what the company promised] - [what happened instead] My desired outcome is: [refund / repair / replacement / credit / cancellation / written apology]. Please write the letter in a calm, firm tone. Do not sound angry or dramatic. Include: 1. A short opening that explains the problem 2. A clear timeline of what happened 3. The specific resolution I want 4. A deadline for response of [number] days 5. A closing that is professional but serious Keep it under 400 words. Also give me a second version that is a little stronger in tone, in case the first one is ignored.

Why this prompt works: Good complaint letters are built on facts, not volume. This prompt forces the AI to organize the timeline, which makes the letter easier for a human reader to follow and harder for the company to brush off. Asking for two versions is useful because a first, polite letter is often the best starting point, but a firmer follow-up may be needed if the company stalls. The word limit also helps the AI stay focused.

One thing to watch out for AI can make a weak case sound polished, but polish is not the same as proof. If you leave out dates, names, receipts, or the exact promise the company made, the letter may sound good and still go nowhere. The best complaint letters feel almost boring because they are so clear. If you are dealing with a big money problem, keep your original records and send the letter from your own name, because the force of the complaint comes from the facts, not the wording.

Know someone who spends too long on things AI could do in two minutes? Forward this to three people who subscribe and I will send you my free AI Prompt Starter Pack: 20 ready-to-use prompts for everyday life.

Next Thursday Turning messy receipts into a simple spending summary and using AI to draft a polite follow-up when someone owes you money.

By Dr. Rowan Hayes


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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