This week we’re looking at two very “grown‑up” uses of AI: **planning a road trip** and **writing a complaint letter that actually gets results**. Both are situations where you have enough life experience to know what you want, but not enough hours in the day to wrestle with details, fine print, or endless back‑and‑forth emails. AI won’t drive the car for you or magically make companies behave, but it can cut the busywork way down.

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 Thursday evening in August, around 7:30 p.m., Martin (59) sat at his kitchen table with a paper map spread out, his iPad open, and a legal pad full of scribbles. He and his wife, Dana, wanted to drive from St. Louis to Glacier National Park in September. They had ten days, a modest budget, and two non‑negotiables: avoid driving after dark, and build in time for short hikes instead of just “car tourism.”

Two hours in, Martin had six browser tabs open: national park websites, Google Maps, hotel searches, a random blog about “best Midwest road trips.” Every time he picked a route, something broke it: too many hours behind the wheel, no decent motels where they needed them, or backtracking that doubled their driving. He’d heard that “AI can plan your trip,” but also that AI sometimes makes things up, and he was not interested in getting stranded because a chatbot invented a gas station in rural Montana.

What he really needed was not a magic answer - but a reasonably good first draft of an itinerary and route that he could then tweak and verify, instead of starting from zero.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

Copy/paste this into your AI of choice (ChatGPT, Copilot, Gemini, etc.), then adjust the cities and dates:

I want you to act as a **road trip planner** for two adults in their 50s who prefer slower travel.

Here are the basics of the trip: - Starting point: St. Louis, Missouri - Final destination: Glacier National Park, Montana (west side entrance) - Dates: September 10 - 20 (10 days total, including driving days) - Daily driving limit: No more than 6 hours of actual driving per day - Budget level: Moderate (we’re fine with mid-range chain hotels or clean motels, not luxury) - Interests: Short hikes (1 - 3 hours), scenic viewpoints, small towns, interesting local food, historic sites - Things to avoid: Interstates all day if there is a more scenic alternative that doesn’t add more than 90 minutes, driving after dark, nightlife, shopping malls

Please: 1. Propose **two different route options** from St. Louis to Glacier and back, both in a loop if possible, and explain the main differences (for example, more national parks vs. more small towns). 2. For the route you think fits our preferences best, create a **day‑by‑day itinerary** that includes: - Starting point and ending point each day - Approximate driving time and major roads - 1 - 2 suggested stops (short hike, scenic viewpoint, or small town) with a sentence on why each is worth stopping 3. Flag any **long stretches without many services** where we should plan ahead for gas and food. 4. At the end, give me a short checklist titled “Things to double‑check before booking” that reminds me to verify hotel availability, road closures, weather, and opening hours on official websites.

Before you give the final answer, **think step‑by‑step** about the driving times, the sequence of stops, and whether each day feels reasonable for two people in their 50s who don’t like to rush.

Why this prompt works:

You’re telling the AI who you are (age, travel style), what you care about (scenic, shorter drives, small towns), and what you want the output to look like (two route options, then a detailed day‑by‑day plan plus a checklist). Tools like Copilot and other AI trip planners explicitly recommend being specific about your dates, interests, and constraints for better results. Asking it to “think step‑by‑step” and flag long service gaps helps catch unrealistic days before you ever get in the car.

AI is very good at *structure* and *ideas*, but not always good at *current details*. It might suggest a restaurant that closed last year or underestimate how long a mountain road takes to drive. Treat the itinerary as a draft, not gospel: verify hotels, road conditions, and opening hours on official sites, and cross‑check key legs in Google Maps or your own GPS. Also, AI tends to be optimistic about how much you can do in a day; if you like slow mornings or long dinners, trim the schedule yourself.

Use Case 2 of 2

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

On a Monday morning at 9:15 a.m., Anita (63) sat staring at an email from her credit card company that made her blood pressure spike. She’d been charged a $275 “no show” fee by a hotel she absolutely had checked into - a mix‑up at the front desk that she thought was resolved months ago. She’d already spent 45 minutes on hold with the hotel and another 30 with the credit card company, only to be told, “You’ll need to submit your complaint in writing.”

In the past, Anita would dash off something like, “This is unacceptable, I’ve been a loyal customer for years, please fix this immediately.” She knew, from experience, that these emails often sank into a black hole or returned with a canned response that didn’t address the actual issue. She didn’t want to be rude, but she did want someone with authority to look at her case, see that the facts were clear, and fix the charge.

What she really needed was a letter that was firm but professional: clear facts, specific ask, and just enough legal‑sounding structure to make it hard to ignore - without turning into a rant.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

You’ll use AI in two steps: first to structure your story, then to polish the letter. Step 1 helps you think clearly; step 2 helps you sound effective.

Step 1 - organize the facts

Copy/paste this and fill in the brackets:

Help me organize the facts for a clear, effective complaint letter about a billing problem.

Here are the key details: - Company name: [Company or hotel name] - My relationship to them: [e.g., credit card customer since 2012, hotel guest, etc.] - What went wrong (in plain language): [Brief description of the problem in your own words] - Dates and amounts involved: [Date(s) of stay or transaction, amount charged, incorrect fee, etc.] - Evidence I have: [e.g., email confirmations, receipts, names of staff I spoke with, call dates] - What I want them to do: [e.g., reverse the charge, refund a specific amount, correct my account record] - Deadline or urgency: [e.g., “This is affecting my ability to pay my bill on time” or a date by which you need a response]

First, please: 1. Lay out the facts in a clear timeline. 2. Identify any details that are missing or unclear that would be important for a complaint. 3. Suggest a simple structure for my letter with short headings (for example, “Background,” “Issue,” “Requested Resolution”).

Do not write the full letter yet. Just help me get the facts straight and the structure clear.

Step 2 - write the letter

Once you have that, take the AI’s timeline/structure, and run this:

Using the organized facts and structure we just created, write a **polite but firm complaint letter** that I can send by email.

Requirements: - Address it generically to “Customer Relations” unless I’ve provided a specific name. - Use a calm, professional tone. No sarcasm, no threats. - Start with a brief summary of the issue and what resolution I’m requesting. - Then present the facts in a simple, chronological order using clear paragraphs. - Refer to key evidence I have (like confirmation numbers or receipts) but do not invent any details. If information is missing, leave a placeholder like [reservation number] for me to fill in. - End with a specific request and a clear, reasonable timeframe for a response (for example, 10 business days). - Keep the final letter under 500 words.

Before you show me the final letter, quickly check: - Is the request realistic? - Is the tone respectful but assertive? If not, adjust accordingly, then present the final version.

Why this prompt works:

Most people jump straight to “Write a complaint letter,” which produces something generic and easy for a company to ignore. Here, you first make the AI help you think: timeline, missing facts, and structure. That matches how good human advocates work - they clarify the story before they write. Giving specific requirements (tone, word limit, placeholders instead of made‑up details, and a response timeframe) pushes the AI toward something you can safely send and fine‑tune, not a puffed‑up template.

AI will happily **invent** specifics if you let it. That’s deadly in a dispute. Insist that it only use facts you’ve provided, and check the letter line by line against your records before sending. Also, be careful if you escalate to mentioning regulators, lawyers, or “legal action”; AI sometimes over‑dramatizes that kind of language. You want firm and credible, not blustery.