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June 18, 2026

Issue 25: Smarter by Thursday

Smarter by Thursday — Issue 25

Issue 25 · week of June 15, 2026

Smarter by Thursday

One practical AI win, every week. No jargon required.

By Dr. Rowan Hayes · Estimated read time: 6 minutes

This week we’re looking at two places AI can save you time, money, and aggravation: **planning a road trip** and **writing a complaint letter that actually gets results**. Both are situations where most people either wing it or stew about it - then spend hours on Google or rewriting the same email five times. AI can quietly take the heavy lifting off your plate, while you stay in charge of the decisions and the tone.

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 Tuesday night in late June, around 9:30 p.m., Maria is at her kitchen table with a yellow legal pad, two guidebooks, and six browser tabs open. She’s 57, lives in Ohio, and wants to drive to Asheville and the Blue Ridge Parkway with her husband for a week in September.

She’s trying to balance a dozen things in her head: how many hours they actually like to be in the car in one day, whether their budget can handle “cute inn” prices, if the hiking she’s bookmarking is realistic for her slightly cranky knees, and what days the Biltmore House is less crowded. Every time she looks something up, she falls into another rabbit hole of “Top 27 Things to Do” lists. Forty minutes in, she has two half-finished lists and no actual plan.

This is where AI is useful: not as a magic travel agent, but as a **fast, flexible planning assistant**. It can take all your preferences, dates, and limits and turn them into a draft itinerary you can react to. You still verify details and make bookings yourself, but you don’t start from a blank page.

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

Copy/paste this into your AI tool and fill in the brackets with your specifics.

> You are my personal road trip planning assistant. > > I want to plan a driving trip. Here are the details about us and the trip: > - Travelers: [who is going, ages, any mobility limits, fitness level] > - Travel style: [relaxed / fast-paced / love museums / prefer nature / hate crowds / prefer local diners over fancy restaurants, etc.] > - Trip dates: [start and end dates, or month and approximate length in days] > - Starting point and ending point: [city/region] > - Maximum daily driving time: [e.g., 4 - 5 hours of driving per day] > - Total budget range for the whole trip (excluding gas): [rough number or range] > - Accommodation preferences: [motels / midrange hotels / B&Bs / avoid Airbnb / need pet-friendly, etc.] > - Must-see stops or experiences: [e.g., “drive part of the Blue Ridge Parkway,” “1 - 2 easy hikes under 3 miles,” “one day with no driving at all,” specific towns you want to include] > - Things to avoid: [e.g., “no fancy tasting menus,” “avoid dirt roads,” “no late-night driving,” “minimum 2-night stay in each place”] > > Using this information, create a **day-by-day road trip plan** for [number] days that: > - Keeps each day’s drive within my maximum driving time. > - Groups stops in a logical driving order (no backtracking). > - Suggests 1 - 3 lodging options in each overnight town in a moderate price range, with the neighborhood or area noted. > - Suggests 2 - 3 activity ideas per day (mix of outdoors, culture, and relaxed options that fit our fitness level). > - Suggests 2 - 3 specific restaurant or café ideas per day that match our preferences. > > Present the plan in a table with columns: Day, Overnight Location, Approx. Drive Time, Main Route, Activities, Food Suggestions, Lodging Suggestions, Notes. > > At the end, add a short section titled “Things to double-check” listing items I should personally verify (like opening days, seasonal closures, road work, or current prices).

Why this prompt works:

You’re treating the AI like a human trip planner: you define its **role**, give it a **clear picture of who you are and how you like to travel**, set **hard limits** (driving time, budget, knees that don’t love steep trails), and ask for a **structured output** instead of a blob of text. The “Things to double-check” section nudges it to admit where you need to verify details, which is exactly how experts say you should use AI for travel planning.

One thing to watch out for

AI can and does make up specifics - particularly about opening hours, prices, and sometimes even restaurant names. Always click through to real websites or maps to confirm anything you plan to book, and double-check that the driving times and routing make sense for *you*, not for a 25-year-old road warrior. If a suggested day feels rushed on paper, it will feel worse in real life, so ask the AI to adjust and slow it down.


Use Case 2 of 2

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

On a Wednesday afternoon, around 3:15 p.m., James is staring at his laptop drafting an email he does not want to write. He’s 63, semi-retired, and usually pretty even-tempered. Two months ago he bought a new washing machine from a big-box store. It’s been leaking since week one. The first service visit didn’t fix it. The second technician never showed.

He has notes in a spiral notebook with dates, names, and ticket numbers. He’s also got three half-written emails in his Drafts folder: one too angry to send, one so polite it barely sounds like a complaint, and one long, rambling saga no customer service rep will read to the end. He wants a clear outcome: either a working machine within a week or a replacement. But putting that into firm, professional language is exhausting.

AI is very good at drafting **structured, calm, firm letters** when you give it the facts and the outcome you want. It won’t feel your frustration, so it won’t vent - but that’s exactly what gets you taken seriously instead of dismissed as “difficult.”

Here is the exact prompt to use:

Copy and paste this into ChatGPT or Claude:

> You are my professional writing assistant. Help me draft a clear, firm, and polite complaint letter about a consumer problem so I have the best chance of getting a fair resolution. > > I will paste the key facts below. First, read them and then ask me up to 5 clarifying questions to make sure you understand the situation and what I want. After I answer, write the letter. > > Here are the facts of my situation (use these as bullet points, not as the final letter): > - Product or service: [what it is, brand/model if relevant] > - Company: [company name] > - Purchase date and price: [date, amount] > - Where I purchased it: [store/website] > - What went wrong: [brief description in plain language] > - What I have already tried: [calls made, emails sent, service visits, promises made, etc., with dates if you have them] > - Any documentation: [order numbers, ticket numbers, photos, receipts] > - How this has affected me: [time lost, money spent, inconvenience, safety concerns, etc.] > - What outcome I want: [refund, replacement, repair by a certain date, additional compensation, etc.] > - Tone I want: [calm and firm / disappointed but courteous / very formal / conversational but professional] > - Who I’m writing to: [customer service, store manager, corporate executive, regulator/ombudsman, credit card company, etc.] > > After your questions and my answers, draft a letter or email that: > - Opens with a clear purpose sentence (“I am writing to request…”). > - Summarizes the problem in a factual, chronological way (no exaggeration). > - Highlights the key efforts I have already made to resolve it. > - States the outcome I am requesting and a reasonable deadline. > - Uses a respectful but firm tone, with no insults or threats. > - Is concise enough that a busy person will actually read it. > > At the end of the letter, include a short bullet list titled “Attachments” suggesting what I should attach (receipts, photos, prior emails, etc.).

You would then paste your bullet-point facts under that prompt and let the AI ask you follow-up questions. Answer them briefly, then let it draft.

Why this prompt works:

You’re not asking the AI to “write an angry letter.” You’re asking for a **professional advocate** who builds a clear narrative from your facts and focuses on the **specific remedy** you want. By having it ask clarifying questions first, you force it to understand the situation instead of filling in gaps with generic language. The structure you specify - purpose, facts, efforts, requested outcome, tone - matches how effective complaint letters are usually written in practice.

One thing to watch out for

AI will sometimes over-promise on your behalf, using language like “I expect immediate resolution” or hinting at legal threats when that’s not your intention. Always read the draft slowly and edit phrases that feel too aggressive, too soft, or simply not like you. Also, double-check any references to “consumer law” or “statutory rights” - AI often invents legal citations or obligations, and you do not want to claim legal rights you don’t actually have.


Know someone who spends too long on things AI could do in two minutes?

Forward Smarter by Thursday to three people who subscribe and I will send you my free AI Prompt Starter Pack: 20 ready-to-use prompts for everyday life.

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Smarter by Thursday · By Dr. Rowan Hayes · drrowanhayes.com
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