This week we’re going very practical: first, how to use AI to plan a relaxed, realistic road trip without falling down a dozen Google rabbit holes, and second, how to write a complaint letter that actually gets a useful response instead of a canned “we apologize for the inconvenience.” Both are things most adults deal with: travel planning and getting companies to do the right thing. AI can make both faster and less stressful - if you know what to ask and how.

Try at least one before Sunday. That is the whole assignment.

Use Case 1 of 2

Use Case 1: Planning a Road Trip with AI (That Matches How You Actually Travel)

On a Tuesday night in early June, around 8:30 p.m., Mark and Elena were sitting at their kitchen table in St. Louis. Their youngest had just graduated from college, and they wanted to celebrate with a one-week road trip, just the two of them, up to northern Michigan.

Mark had three tabs open: Google Maps, a travel blog from 2018, and a long TripAdvisor thread. Every recommendation seemed to be for “must-see” places that were either crowded, expensive, or aimed at 20-somethings who liked hiking 12 miles before lunch. Elena was tired. She didn’t want “epic.” She wanted two-lane roads, small town cafés, and maybe one nice inn overlooking the water - without spending five hours comparing options.

They’d been “researching” for an hour and had very little to show for it except frustration and a half-finished bag of pretzels. Mark finally said, “I wish someone would just tell us: Here’s a sensible route, here’s where to stop, here’s where to sleep. No nonsense.” That “someone” can be AI - if you describe what you actually want in detail, instead of just typing “road trip Michigan.”

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

- Starting point: [YOUR STARTING CITY/AREA] - Ending point: [YOUR ENDING CITY/AREA OR “LOOP BACK TO START”] - Dates / total days available: [DATES OR “X DAYS TOTAL”] - Daily driving limit: We prefer to drive no more than [X] hours per day. - Pace: We like a relaxed pace. We’d rather see fewer places and enjoy them more. - Interests: [E.g., small towns, local cafés, easy nature walks, bookstores, historic sites, wine tasting, etc.] - Things we want to avoid: [E.g., long hikes, very crowded tourist traps, chain restaurants, night driving, super fancy hotels] - Budget per night for lodging: Approximately [RANGE] per night. - Lodging preferences: [E.g., small inns/bed-and-breakfasts, mid-range hotels, no camping, must have private bathroom, etc.] - Physical considerations: [Any mobility issues, stairs to avoid, need for frequent rest stops, etc.] - Food preferences or restrictions: [E.g., vegetarian, need gluten-free options, dislike spicy food, etc.]

After you ask your 5 questions and I answer them, please create:

1. A day-by-day itinerary with: - Start and end town for each day - Estimated driving time - 1 - 3 suggested stops (towns, parks, or attractions) that match our interests 2. 2 - 3 lodging suggestions for each night (not luxury, but comfortable and well-reviewed). 3. A short explanation each day of why this route and these stops are a good fit for us. 4. A final summary that lists: - Total driving hours - Biggest “don’t miss” stops for our style - Any days that might feel rushed and how to simplify them.

If you’re not sure about a detail, say so and give your best guess instead of making things up. Focus on realism and comfort, not trying to cram in everything.

Why this prompt works:

First, it forces the AI to ask clarifying questions before planning, which is exactly what a good human travel agent would do. Second, it gives constraints (driving time, budget, pace, preferences), which prevent the “Pinterest fantasy itinerary” problem where every day is overloaded. Third, it specifies the output format - day-by-day plan, lodging suggestions, summaries - so you don’t get a vague list of cities, you get something you can actually follow and tweak.

AI can invent specific hotel names, restaurant names, or “hidden gems” that sound real but aren’t accurate anymore - or never existed. Treat the itinerary as a first draft: copy the names into Google Maps, double-check that places are open, and read a few real reviews. Also, pay attention to drive times. What AI calls “3 hours” might be four and a half in summer traffic or on mountain roads; always verify the route in a real map app before you lock anything in.

Use Case 2 of 2

Use Case 2: Writing a Complaint Letter That Actually Gets Results

On a Wednesday morning at 9:15, Denise opened her credit card statement and saw a $487 charge from an airline - months after the trip where everything had gone wrong. Her flight had been canceled after they boarded. They sat for four hours, were given a tiny voucher that didn’t cover a hotel, and she ended up arriving at her niece’s wedding halfway through the reception. The airline had promised a refund for the unused leg “within 7 - 10 business days.” It had been three months.

Denise had already tried calling twice. Both times she’d waited on hold, spoken to someone who apologized cheerfully, promised to “escalate the case,” and then… nothing. When she tried the airline’s online complaint form, she got a robotic email response: “We regret any inconvenience.” No refund. No voucher. No acknowledgment that this wasn’t just an inconvenience; it was missing an important life event.

She wasn’t looking for revenge. She wanted her money back and some recognition that they’d messed up. She also wanted her letter to sound firm and professional, not like an angry Yelp review. This is where AI can help you structure a letter that hits the right notes: clear facts, reasonable request, polite but serious tone, and a hint that you know your rights.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I need help drafting a firm but professional complaint letter that is likely to get a real response, not a generic apology. I will paste the facts of my situation below. Please do the following:

1. Ask me up to 5 clarifying questions to make sure you understand the situation, the timeline, and what resolution I’m seeking. 2. Then draft a letter I can send by email or physical mail that: - States the facts and dates clearly and briefly - Explains the impact on me in a calm, non-dramatic way - References any relevant policies, guarantees, or consumer rights (if you know them) - Clearly states what I want them to do to fix this (refund, credit, replacement, etc.) - Sets a reasonable deadline for response (e.g., 10 business days) - Is polite but firm, and sounds like it’s written by an adult, not a lawyer or an internet troll

Here are the facts of my situation: [Paste your story here: dates, times, order/booking numbers, who you spoke with, what was promised, what actually happened, what you want.]

When you write the letter, please: - Use plain language at about an 8th - 10th grade reading level. - Keep it to 3 - 6 short paragraphs. - Include a clear subject line and a suggested email closing (with my name left as [YOUR NAME]). - Offer a version I can send directly to the company AND a brief, more formal version I could send to a regulator or consumer protection agency if needed.

If you are not sure about specific legal rights in my country or state, say so and keep the language general rather than guessing.

Why this prompt works:

It tells the AI to ask questions first, which improves accuracy and keeps the letter focused. It also gives clear instructions about tone, length, and structure, so you don’t get something that sounds like a legal brief or an emotional rant. By explicitly asking for both a company-facing version and a regulator-facing version, you get options: one to resolve the issue quietly, and one as backup if they ignore you.

AI is not your lawyer and can be overconfident about laws or regulations. If it cites a specific law, rule, or government agency you don’t recognize, look it up before sending, or strip out the legal references and keep the general language (“according to your stated refund policy,” “under applicable consumer protection laws”). Also, remember that even a beautifully written letter isn’t a magic wand. Some companies respond well; others don’t. Use the AI draft as a strong starting point, then adjust it so it genuinely sounds like you.