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Good morning. Today's issue is about AI being confidently wrong, first about your calendar, then about you. The tutorial teaches AI to ask before it answers, which would have saved a few headaches around here too.
AI INSIGHT
Your AI Remembers You. Just Maybe Not Correctly.
I've gotten into the habit of telling Claude and ChatGPT what day it is before I ask them anything else, because left alone, both will tell me, with total confidence, the wrong date. It's genuinely funny, and a little stunning, that neither has a built-in calendar. But confident and wrong is exactly the pattern underneath AI's other new trick: remembering things about you between conversations.
Every major AI tool now quietly stores details between chats: your job, your kids' names, a project you complained about back in March. It's supposed to feel like it knows you. The problem isn't that it forgets. It's that it remembers wrong, just as confidently as it gets the date wrong, and a stored detail can get flattened, generalized, or never updated while still coming back sounding certain.
That's worth actually checking, not shrugging at. Most tools now let you view, edit, or delete what they've stored about you, usually a few menus deep in settings.
The catch: deleting bad memory doesn't undo the responses it already shaped, and most people never look at what's stored until something feels off.
FROM OUR PARTNER
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AI TUTORIAL
The 10 Questions AI Should Ask Before It Answers You
Working on this very newsletter, Claude has occasionally mixed up which issue we're on or what day it publishes, not the facts inside a story, just the production details around it. To be fair, it catches just as many mistakes I make. Both point at the same thing: AI answers instantly, even when it's missing a detail that would change the answer completely. Bring it a real decision, not just a production schedule, and the stakes get higher.
1. Bring your real decision or project in one or two plain sentences, without over-explaining it upfront.
2. Ask AI to interview you with its own questions before it gives you an answer, not the other way around.
3. Tell it explicitly: ask at least ten clarifying questions, one at a time, before responding with a plan.
4. Answer honestly, including the details that feel too obvious or too personal to mention.
5. Once it has enough, ask it to summarize what it now understands before it moves to advice.
6. Correct anything it got wrong in that summary before letting it continue.
Try This With AI What it does: It forces AI to gather the details that actually change the answer, instead of handing you generic advice built on guesses. "Act as a thoughtful consultant helping me with a decision. My situation: [describe your decision or project in one or two sentences]. Before you give me any advice or a plan, ask me at least ten clarifying questions, one at a time, waiting for my answer before asking the next. Once you have enough information, summarize what you understand, then give me your actual recommendation." Customize it: Swap in whatever real decision you're facing, from a home renovation to a family conversation you're dreading. |
If it does not work: it ignores the instruction and answers immediately anyway. Stop it and say plainly: do not answer yet, ask your questions first, one at a time.
What this doesn't fix: more questions from AI doesn't mean better judgment, especially for decisions involving other people's feelings or money you can't easily undo.
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NEWS YOU CAN USE
This Matters at Home
Short, practical summaries to help you stay updated on recent AI news—and what it means for everyday life.
✈️ Google's AI Mode Just Became Your Pushiest Travel Agent. Google's AI Mode can now track flight prices and help book hotels right inside search, so you can plan a trip without forty open browser tabs.
🎓 Every Teacher In A School District Can Now Get Claude For Free. A district signs up once and every educator gets access, single sign-on included. Sign up by June 2027 and the first year is free.
📺 That Viral Kimmel Clip You Shared? Might Be A Robot. AI deepfakes of Jimmy Kimmel and Jon Stewart are racking up hundreds of thousands of views online, and most viewers can't tell the difference. Stay skeptical.
🔒 The Best Free Tools For Keeping Your Data Out Of AI. One tool strips your name and address from text before you paste it into a chatbot. Another transcribes meetings entirely on your laptop, nothing uploaded.
REAL WORLD
How We Used AI This Week
Real people, real uses—here’s how AI is quietly making life better, one small win at a time.
🍽️ Carolyn, Spartanburg, SC. She asked AI to build a menu plan from the food she already had on hand, for two adults and two dogs. One of them manages diabetes, the other hypertension, plus a shared preference for less heat and more sweetness. The first draft needed fine tuning to match actual grocery prices, but the final plan worked around both conditions and both palates. Two humans, two dogs, one week of meals nobody had to cook twice.
READER POLL
Has your AI assistant ever confidently told you something about yourself, or even just the date, that was flat wrong?
TOOLS FOR YOU
🔒 Tool Spotlight: NordVPN
If today's lead has you thinking about what AI tools remember and share, your internet connection is the bigger leak most people never check. NordVPN encrypts your connection and hides your location from the sites and apps you visit, including the ones quietly training AI on browsing patterns. Setup takes about two minutes across your phone, laptop, and browser. Start here.
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