Planning a summer road trip and dealing with companies that don’t do what they promise sound like two totally different problems. In practice, they have the same bottleneck: you’re trying to make good decisions with limited time and partial information. This week, we’ll use AI for both - first to design a **road trip that feels like you**, and then to write a **complaint letter that gets results instead of getting ignored**.

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 July, Denise - 58, lives in Ohio - sat at her kitchen table with a legal pad and a half‑cold cup of tea. She and her husband Mark had two weeks off in August. They wanted to drive somewhere “out West,” maybe see some national parks, maybe a few interesting towns.

Denise did what most of us do: opened three tabs - Google Maps, a travel blog somebody sent her, and a Facebook group full of long comment threads. Within 30 minutes she had six different possible routes, four hotel options per night, and no clear idea of how long anything would take. She knew they didn’t want to drive more than six hours a day. She knew Mark’s knee couldn’t handle long hikes. And she knew if she kept scrolling, they’d still be “planning the trip” three weeks from now.

What she *didn’t* know was that AI could take her messy notes - preferences, constraints, and half‑formed ideas - and turn them into three clear options with trade‑offs explained: more scenery vs. fewer hotel changes, cheaper vs. more comfortable, slower pace vs. seeing more.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

> You are my road trip planning assistant. I am in my late 50s and I want a realistic, enjoyable driving trip, not something exhausting or designed for 25-year-old backpackers. > > Here are my constraints and preferences. Read them carefully, then ask me up to 5 clarifying questions *before* you design anything: > - Starting city: [YOUR CITY] > - Dates or rough timing: [DATES OR “ABOUT 10 DAYS IN LATE AUGUST”] > - Who’s going: [NUMBER OF PEOPLE, AGES, ANY MOBILITY ISSUES] > - Daily driving limit: [MAX HOURS YOU WANT TO DRIVE PER DAY] > - Total trip length: [NUMBER OF DAYS] > - Budget/comfort level: [“BUDGET”, “MID‑RANGE”, OR “COMFORTABLE BUT NOT LUXURY”] > - Interests: [E.G. SCENIC DRIVES, SMALL TOWNS, GOOD FOOD, LIGHT HIKES, MUSEUMS, LIVE MUSIC] > - Things to avoid: [E.G. VERY LONG HIKES, BIG CROWDS, CHAINS RESTAURANTS, EXPENSIVE RESORTS] > - Special needs: [E.G. BAD KNEE, HATES HOT WEATHER, NEEDS EV CHARGING, ETC.] > > After you ask and I answer your clarifying questions, propose **3 different itinerary options** for a road trip that matches my constraints. For each option, include: > 1. A short description of the overall “feel” of the trip. > 2. A day‑by‑day outline with driving time estimates, major stops, and suggested towns to stay in. > 3. The main trade‑offs vs. the other options (for example: more scenic but more driving, cheaper but fewer restaurant choices, etc.). > > Very important: > - Assume you might be wrong about details like opening hours or road closures. Do **not** tell me to book anything directly from your suggestions. > - When you’re unsure or the information might be outdated, say “This needs to be verified with Google Maps or official sites.” > - Keep the tone practical and aimed at travelers in their 40s - 70s who want a comfortable, interesting trip, not an extreme adventure.

Why this prompt works:

This prompt gives the AI exactly what good trip planners need: clear constraints (where, when, who, how long, budget), personal preferences, and deal‑breakers. It also tells the AI to *ask questions first*, which improves the quality of what you get back. Requesting three options with trade‑offs forces it to think in terms of comparison - helpful when you’re deciding between “more nature” and “less driving.”

AI is not a live travel agent. It doesn’t see today’s weather, road closures, or whether a specific restaurant is still in business. Treat its suggestions as a draft, not a final plan: verify driving times and key stops in Google Maps, check hotels on Booking.com or similar sites, and confirm any ticketed attractions on official websites. And watch for over‑packed days - AI often assumes you want to fit in “just one more thing” when your future self would prefer a nap.

Use Case 2 of 2

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

On a Monday morning in early July, Carlos - 62, retired teacher in Arizona - opened his credit card bill and saw a charge for $189 from a hotel he never stayed in. He had booked, then canceled well within the stated free‑cancellation window. The hotel’s website even showed “Canceled.” But the charge was still there.

Carlos did what many of us do: he called customer service, waited on hold, explained the situation, and was told, “We’ll look into it.” Two weeks later, nothing had changed. The charge was still there.

He knew he needed something more formal - a written complaint that would go to the right place and make it clear he wasn’t going away. But he didn’t want to sound angry or unhinged. He wanted to sound like an adult who knows his rights, has documentation, and expects a timely fix. He’d written plenty of letters in his life, but he wasn’t sure how to structure one that would cut through the noise.

This is where AI can quietly shine: taking your notes, dates, and documents and shaping them into a clear, firm, professional letter - whether it’s to a hotel, an airline, a contractor, a doctor’s office, or a subscription service that “forgot” to cancel.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

> You are my professional writing assistant. I need a clear, firm complaint letter that is likely to get a result, not just a generic apology. > > First, ask me up to 7 questions to understand the situation and gather key facts. Then draft the letter. > > Here is what you should ask about: > - Who the letter is going to (company name, department if known). > - What went wrong (in plain language). > - Key dates and amounts (purchase date, cancellation date, dollar amount, account numbers). > - What I’ve already tried (phone calls, emails, chats, who I spoke to, any case numbers). > - What outcome I want (refund, correction to my record, written confirmation, etc.). > - Any relevant policies or laws (for example, “free cancellation until [date]” or local consumer laws I know about). > - My tolerance level: do I want very firm wording, or polite but still clear. > > After I answer, draft a one‑page letter that includes: > 1. A short, factual summary of the problem at the top. > 2. A timeline of key events in 3 - 5 sentences. > 3. A clear statement of what resolution I expect and by when. > 4. A mention of any documentation I am attaching or can provide (screenshots, emails, receipts). > 5. A calm but firm closing that makes it clear I will escalate if necessary (for example, disputing the charge with my bank or contacting a regulator) without sounding threatening. > > Important instructions for the tone and wording: > - Write for an adult in their 40s - 70s: professional, composed, not dramatic. > - Avoid legal jargon unless absolutely necessary; explain any legal terms in plain language. > - Do **not** invent laws or policies. If you reference laws, phrase it like: “I understand that under [type of law], customers are entitled to…” rather than citing specific codes I haven’t confirmed. > - Keep the letter specific to my situation - not a generic template. Use concrete details I’ve provided.

Why this prompt works:

You’re telling the AI to operate like a good paralegal: gather facts first, structure the story second, and then make a specific request with a deadline. The instructions about tone keep it out of “internet outrage” territory and in the realm of calm, credible complaint. Asking for a timeline and clear expected resolution ensures your letter gives the recipient something concrete to do, which increases the odds of action.

AI is not your lawyer and it can easily over‑state your rights if you let it. That’s why the prompt explicitly tells it *not* to invent laws or cite specific codes you haven’t checked. Read the letter carefully before sending, remove anything you’re not comfortable standing behind, and make sure all dates, amounts, and descriptions match your records. And remember: a strong letter helps, but some companies still ignore things - be prepared to follow through on whatever escalation you mention (bank dispute, regulator, small‑claims court, etc.) if they don’t respond.