Planning a road trip and writing a complaint letter do not sound like “AI problems.” They sound like “Saturday morning at the kitchen table with a legal pad” problems. But these are exactly the kinds of real-life situations where AI can quietly save you hours, help you think more clearly, and give you language you might not come up with on your own. This week we’ll look at two specific, very practical cases: **using AI to plan a road trip** and **using AI to write a complaint letter that actually gets results.**

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 Wednesday evening in late June, around 7:30 pm, Maria (56) is at her dining table in Columbus, Ohio. Her husband has just said, “If we don’t book something by this weekend, we’re not going anywhere this summer.” Their adult daughter is joining them for part of the trip, they want to drive somewhere new, and the constraints are piling up: no more than 6 hours of driving a day, dog-friendly hotels, nothing too strenuous for Maria’s knee, and they’d love some small towns instead of just big cities.

Maria has spent an hour bouncing between Google Maps, hotel sites, and travel blogs. Every time she picks a place, she realizes she hasn’t checked how long the next day’s drive is, or whether there’s anything to actually *do* there. She’s tired, a little annoyed, and thinking, “This is why people pay travel agents.”

This is where AI is useful: not as a booking engine, and not as a crystal ball, but as a very fast, very patient planning assistant that can turn your vague idea (“maybe a loop through Michigan?”) into a structured, day-by-day draft itinerary you can then refine and fact-check.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

> I want you to act as my road trip planning assistant. > > Here are the basics of the trip: > - Starting point: Columbus, Ohio > - Trip length: 7 days, round trip by car > - Travel dates: [insert your approximate dates or month] > - Daily driving limit: no more than 5 - 6 hours of driving in a day > - Who’s going: two adults in our 50s plus our adult daughter for the first 3 days > - Physical needs: one of us has a bad knee, so no long hikes or lots of stairs > - Interests: charming small towns, lake views, short easy walks, good local food, bookstores, and interesting history > - Budget level: mid-range hotels or well-reviewed motels, no luxury resorts > - Dog-friendly: please assume we have a dog with us and avoid places that obviously wouldn’t allow pets > > Step 1: Ask me up to 8 clarifying questions about our preferences (for example, which direction we’d like to go, whether we prefer one or two bases vs moving every night, any states we especially want to visit, etc.). Do NOT plan the trip yet. > > Step 2: Once I answer your questions, propose 2 different 7-day road trip route options starting and ending in Columbus, Ohio. For each option, include: > - A short overview of the route and why it fits our preferences > - A day-by-day plan with: driving time, key towns or stops, 2 - 3 activity ideas, and 1 - 2 neighborhoods or areas where it would make sense to stay the night > - At least one “flex day” where we could slow down, skip something, or stay longer if we’re tired > > Step 3: At the end, list 8 - 10 items I should double-check myself (hotel options, road closures, seasonal hours, dog rules, etc.), and suggest what to copy into Google Maps or another map app to sanity-check the route. > > Important: > - Keep suggestions realistic for people in their 50s/60s, not 20-somethings racing through 6 cities. > - Space activities in a way that doesn’t feel rushed. > - If there are multiple interesting options for a day, present them as “Option A / Option B” so we can choose.

Why this prompt works: You are giving the AI **constraints** (start/end point, driving limits, physical needs), **preferences** (small towns, lakes, bookstores), and a **clear structure** (ask questions first, then present two options, then a checklist to verify). You’re not asking it to “find deals” or “book things,” just to create a thoughtful draft itinerary. You also explicitly tell it to think about your age and energy level, which most tools will otherwise ignore.

Use Case 2 of 2

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

On a Monday afternoon around 2:15 pm, Derek (62) is staring at an email draft to an airline. He is not a chronic complainer. But last month, his flight was cancelled with almost no notice, he was stuck overnight in a strange city, and the rebooked flight put him in the middle seat of the last row for a 5-hour flight. He spent over $250 on a hotel and food during that unplanned layover, and the customer service line was a maze of scripts and “we understand your frustration” with no actual resolution.

He’s already sent one short complaint through the airline’s web form and got a generic “we value your feedback” response with a tiny voucher that doesn’t cover half of what he spent. Now he wants to escalate. But he doesn’t want to rant, and he doesn’t know how to structure the letter so that a real person in the right department takes it seriously. He’s annoyed, but he also just wants this off his plate.

This is where AI can help you turn scattered frustration into a **calm, specific, well-structured complaint letter** that: - States the facts clearly - Shows you understand what you’re entitled to (or at least what’s reasonable) - Makes a concrete request - Stays firm but professional, which is exactly what a human agent is more likely to respond to.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

> I want you to help me write a clear, firm, professional complaint letter that has a good chance of getting results. > > Situation: > - Company: [insert company name] > - Type of issue: [e.g., flight cancellation, damaged product, terrible hotel stay, ongoing billing problem] > - Date(s) of incident: [insert date(s)] > - What happened in simple bullet points: > • [example: My flight [number] on [date] from [city] to [city] was cancelled about 2 hours before departure.] > • [example: I was rebooked for the next day and had to pay for my own hotel and meals.] > • [example: I contacted customer service twice and received only a generic apology and a small voucher.] > - Out-of-pocket costs: [list approximate amounts and what they were for] > - Any supporting policies: [mention if you know of relevant laws, company policies, or guarantees, even roughly, e.g., “I believe EU regulations require compensation in cases like this” or “Your website states a 30-day satisfaction guarantee.”] > - What resolution I want: [e.g., full reimbursement of hotel and meals, additional compensation, refund, repair, cancellation of charges, removal of a fee, etc.] > > Please write a concise email (no more than 400 - 500 words) with this structure: > 1. Brief, calm statement of purpose (why I’m writing). > 2. Short timeline of what happened, in order, with key facts and dates. > 3. Clear description of the impact on me (time, cost, inconvenience), without emotional language or insults. > 4. Reference to any relevant policy or consumer rights, in plain language, without sounding like legal threats. > 5. A specific, reasonable request for what I would like the company to do. > 6. A polite but firm closing that invites a response within a reasonable time frame (for example, 10 - 14 days). > > Important: > - The tone should be calm, respectful, and confident, not angry or dramatic. > - Do NOT apologize for raising the issue. > - Avoid over-the-top language (no “worst experience ever,” “outrageous,” or similar). > - Make it easy for a busy customer service person or supervisor to see the facts and approve a fair resolution. > > After you draft the email, suggest 3 - 5 specific subject lines that are likely to get attention without sounding spammy or aggressive.

Why this prompt works: You’re giving the AI **raw material** (what happened, when, what you spent, what you want) and a **clear structure** for the letter. You’re also instructing it on tone: firm, factual, and respectful instead of emotional or vague. AI is very good at turning messy bullet points into something that reads like it came from a composed, organized adult who knows what they’re asking for and why.