If you’ve ever thought, “I should really figure out this AI thing, but not today,” this week is for you. We’re taking on two very practical problems: **planning a road trip using AI** and **writing a complaint letter that actually gets results**. Neither requires being “techy.” They do require being willing to describe what you want like you would to a thoughtful human assistant - and then letting the machine do the tedious parts.

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 Wednesday night at 8:15 p.m., Diane - 57, lives outside Columbus - sits at her kitchen table with a yellow legal pad and three different web pages open on her laptop. She and her husband want to drive to Asheville next month, maybe swing through Louisville, and possibly stop in a small town with good antiques and a decent diner. Two days ago her sister said, “Just use one of those AI things, it’s way easier,” and Diane nodded politely while thinking, “Sure, I’ll add that to the list of things I don’t understand.”

Right now she’s doing what she’s always done: googling “best stops between Columbus and Asheville,” clicking random articles, and trying to stitch them together into something that makes sense. She’s worried about ending up on endless interstates with nothing interesting to see, or accidentally booking a hotel that’s next to a highway off-ramp and a Waffle House instead of somewhere she can walk around in the evening. She doesn’t want a flashy “Top 10 Road Trips” travel blog; she wants a simple, realistic plan that fits how she and her husband actually travel in their 50s: not rushed, not backpackers, and absolutely not sleeping in the car.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I’m planning a 6-day driving road trip and I want your help as a practical travel planner, not a hype-y blogger.

Here are the basics: - Starting point: Columbus, Ohio - Ending point: Asheville, North Carolina - Dates: October 10 - 15 (flexible by a day) - Travelers: married couple, ages 57 and 60 - Driving preference: no more than 4.5 hours of driving per day, ideally with one interesting stop on the way - Interests: walkable downtowns, local diners or cafés, small museums, scenic drives, light hiking (2 - 3 miles), antiques and used bookstores - Avoid: big party scenes, super-touristy “must-see” spots, very expensive restaurants, complicated parking - Budget: mid-range (okay with decent hotels, don’t need luxury)

Please: 1. Suggest a realistic day-by-day route with specific towns to stay in each night. 2. For each day, list: - departure and arrival towns - approximate driving time - one scenic or interesting stop on the way - 2 - 3 ideas for simple activities in the arrival town that evening 3. Focus on places that will feel comfortable and interesting to travelers in their 50s and 60s, not aimed at 20-somethings. 4. Then give a short checklist I can use to sanity-check your plan (things like “check actual driving times,” “confirm hotel prices,” etc.).

Ask me 3 - 5 clarifying questions at the end if anything is vague or you need more detail about our preferences.

Why this prompt works:

This prompt tells the AI what role to play (“practical travel planner”), gives concrete constraints (dates, driving limits, interests, budget), and is explicit about what to avoid. That keeps it from giving you a generic “top attractions” list and pushes it toward a usable daily plan. Asking for a sanity-check checklist and clarifying questions forces the AI to treat this like a real plan, not a travel fantasy.

AI will happily invent restaurants, shops, or small attractions that sound plausible but don’t exist or have closed. It’s very good at structure, not perfect on facts. Use its plan as a **draft**, then check every specific recommendation in Google Maps or similar before you commit. Also, because it can’t see current traffic, weather, or construction, treat drive times as rough estimates and adjust based on reality.

Use Case 2 of 2

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

Friday morning at 9:30 a.m., Luis - 62, semi-retired, lives in Phoenix - opens yet another email from his health insurance company. It’s the final denial on a claim for a routine test his doctor ordered. The test was “out of network,” although no one mentioned that at the time, and now he’s sitting on a $780 bill. He’s written three drafts of a complaint letter over the last week. The first was too angry, the second too polite, and the third one he never sent because he wasn’t sure it made sense.

Luis is not looking for a philosophical debate about the healthcare system. He wants one thing: a letter that gives him the best chance of having this decision reconsidered, or at least escalated to a supervisor who will look at it carefully. He’s tired of feeling like the only options are yelling (which he suspects will get him ignored) or rolling over and paying the bill. His wife forwarded him an article about “AI writing assistants,” but when he tried typing, “Write a complaint letter to my insurance” into a chatbot, the result sounded like a corporate robot talking to another corporate robot. He thought, “If I send this, they’ll just put it in a pile with the other auto-generated junk.”

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

I need help drafting a clear, firm, professional complaint letter about a denied health insurance claim. I want it to sound like a thoughtful adult wrote it, not like a generic template.

Here are the facts (please organize them into a coherent letter): - I am a long-time customer of [Insurance Company Name], insured since [Year]. - Claim number: [Claim Number] - Date of service: [Date] - Provider: [Doctor or Facility Name] - The test/procedure: [Brief description] - The denial reason given: “[Quoted reason from the denial letter]” - Why I believe this denial is unfair or incorrect: [Your explanation in 3 - 5 bullet points, e.g. “provider was recommended by in-network doctor,” “no one informed me it was out-of-network,” “this test is standard of care for my condition,” etc.] - What I am requesting: reconsideration of the claim and coverage for this service, or a detailed written explanation of why coverage is being denied, referencing the specific policy language.

Please: 1. Write the letter in my voice: plain language, respectful but firm, and specific about the facts. 2. Use short paragraphs and avoid legal jargon. 3. Include: - a brief opening stating the purpose of the letter - a clear summary of the situation and timeline - a concise explanation of why the denial should be reconsidered - a specific request and a reasonable deadline for response 4. At the end, include a separate bullet list titled “Key points from this letter” that I can use if I need to speak to someone by phone.

Before you write, ask me 3 questions to clarify anything that is unclear or missing.

Why this prompt works:

Here you’re feeding the AI the **raw material** - dates, claim number, reasons - then asking it to organize and tone it, not invent anything. You’re very explicit about style (“plain language, respectful but firm”) and structure (opening, summary, explanation, request). That keeps it from producing fluffy corporate-speak and helps you get a letter that sounds like a careful human, not a script.

AI has no idea what your actual insurance policy covers, and it can’t give legal advice, even if it sounds confident. It will sometimes slip in grand statements like “according to standard practices” or “this clearly violates your obligations” - delete anything that goes beyond the facts you’ve given or sounds like a lawyer talking. Before sending, read the letter aloud to yourself; if any sentence feels too aggressive or too vague, edit it to match how you’d speak on the phone.