Small Steps with AI

Jill McKinley
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AI isn't just a search engine. It can help you think through a hard decision, organize your house, plan your retirement, and sometimes — if you let it — say exactly what you needed to hear. Small Steps with AI is hosted by Jill from the Northwoods, a real person figuring out how this technology fits into real life. No coding. No hype. Just small steps.

  1. 6d ago

    What Not to Share with AI

    AI can explain, compare, draft, and troubleshoot, but useful assistance does not require handing over every private detail. I walk through a practical circle of trust for information, safer ways to share documents, and the extra care needed when AI suggests computer commands or advice with serious consequences. Ask Three Questions Before SharingWhat does AI actually need to know? What happens if its answer is wrong? What would happen if the information were exposed? These questions help separate relevant context from unnecessary identifying details and keep our judgment involved as tools become more capable. Red, Yellow, and Green InformationPasswords, login codes, recovery keys, and full account identifiers belong in the red category. Health, financial, employment, and other people's private information require careful judgment in the yellow category. Generalized examples and nonidentifying context can often provide a greener way to get useful help. Protect Other People and Work MaterialsA friend's diagnosis or a coworker's private situation is not ours to disclose casually. Workplace rules also matter: permission to use an approved company tool does not automatically cover a personal account. I share why checking the rules and removing unnecessary names can make a difference. Look Beyond the Question in a ScreenshotAI may notice more than the detail we intended to show. Documents and photographs can reveal addresses, account numbers, background objects, and other information. Crop to the relevant area and check the finished image before sharing rather than assuming the rest will be ignored. Keep Judgment over Actions and AdviceA command that fixes a problem can also delete files, change permissions, or modify a database. Understand it, make backups, and seek qualified help when needed. For medical, financial, and legal questions, AI can help organize information and prepare questions, while important decisions deserve professional verification. Before your next upload or powerful command, pause and ask the three questions. Share only what is needed, understand proposed actions, and increase verification as the stakes rise. jill@startwithsmallsteps.com and jillfromthenorthwoods.com A note on this podcast: I’m not a software developer or an AI professional, just someone who uses these tools every day and shares what’s working for me. Test anything I mention against your own situation before you rely on it. TIMESTAMPS 00:00 Using AI includes knowing when to pause01:59 Three questions for safer AI use03:05 Relevant context without identifiers06:54 Red information: credentials and codes12:07 Yellow information and privacy14:56 Other people and workplace rules16:39 Green information and general examples18:19 Crop documents and check screenshots20:53 Understand commands before running them23:42 High stakes and your final judgment

  2. Oct 14

    How AI Can Help People With Low Vision

    A listener asked me how AI might help someone with low vision, and that sent me into a series of experiments. I wanted to know what these tools could actually do with tiny print, household products, photographs, instructions, and ordinary objects, and just as importantly, where they could fail. AI Can Help With More Than ReadingA listener question sent me looking at how AI can help people who are blind or have low vision. I tested ordinary situations where a camera, voice conversation, and follow-up questions can turn visual information into something more usable. From Tiny Print to Useful AnswersMagnification and text recognition have been around for years, but generative AI adds another layer. It can read instructions, explain what they mean, answer questions about an object, and sometimes adapt the information to what you actually need. The Tools Are Getting More ConversationalI look at Apple Magnifier and voice features, Microsoft Seeing AI, Be My Eyes, and smart glasses. The interesting change is not simply that technology can recognize something, but that you can keep asking questions about what it sees. AI Can Be Right and Still Miss SomethingOne of my tests produced accurate information while skipping a line entirely. That is an important warning for visual accessibility because a person who cannot see the original may not know that anything was omitted. Match the Verification to the RiskA wrong shirt color is inconvenient. A wrong answer about medication, allergies, finances, legal papers, or physical safety can matter a great deal, so higher-risk situations need another source of verification. Try One Ordinary ThingAI does not replace established accessibility tools, training, specialists, screen readers, or human help. It can be one more flexible tool, and the best first experiment is something small and low stakes. The useful shift is from a tool that simply magnifies or reads to one you can question. Start with something ordinary, keep the stakes low, ask follow-up questions, and learn where AI fits alongside the accessibility tools and people you already trust. Contact: jill@startwithsmallsteps.com | jillfromthenorthwoods.com A note on this podcast: I'm not a software developer or an AI professional, just someone who uses these tools every day and shares what's working for me. Test anything I mention against your own situation before you rely on it. TIMESTAMPS 00:00 AI and low vision03:44 From magnification to conversation05:32 Testing AI on everyday objects07:35 Apple Magnifier and visual questions09:42 When a correct answer is incomplete11:31 Voice control and hands-free help13:35 Seeing AI, Be My Eyes, and smart glasses16:55 The confidence problem19:34 Low stakes versus high stakes23:24 Start with one ordinary task

  3. Oct 7

    I Used AI to Plan a Walking Tour of Marquette

    Someone who runs local walking tours emailed me asking how AI could help him. So I built a pretend scenario: I live in Marquette, Michigan, a friend is coming to visit, and I realize I don't actually know the story of my own town. What happened next shows the most useful AI skill there is, and it isn't prompt engineering. It's asking the next question. **Start With a Plain Question** My first prompt was simple: tell me something interesting about Marquette that I've walked past a hundred times without knowing its story. No role-playing, no special formula. Just a real question about something I cared about. **One Answer Leads to Another** Iron ore led to the Marquette Iron Company of 1849. That led to a settlement first called New Worcester, the Ojibwe community of Chief Charles Kawbawgam and his wife Charlotte, and Father Jacques Marquette, who explored the region nearly two centuries earlier. None of those were in my first question. **The Dock That Washed Away** Marquette's first dock was swept away by Lake Superior almost as soon as it was built. Asking AI to connect that failure to the massive 1931 Lower Harbor Ore Dock turned a concrete landmark I swam beside as a kid into a story about solving one problem over eighty years. **Old Fears About New Technology** The men who moved ore by wheelbarrow watched railroads and pocket docks change their work. The mix of wonder and job worry they felt is the same one many of us feel about AI now. **You're the Editor, Not AI** AI can be wrong, and confidently wrong. If you're going to repeat something to a friend or a tour group, ask for sources, look for a second independent confirmation, and check historical societies, museums, and archives. AI isn't the source. You're responsible for what you repeat. **Lunch Becomes Part of the Tour** A hungry stop turns into history too: the pasty, brought by Cornish miners, adopted by Finnish immigrants, and still a U.P. staple. Then the most useful question of all: "What haven't I asked yet?" You don't need to be a genius to use AI well. Tell it what you're trying to do and who it's for, push back when an answer isn't useful, ask for evidence when something sounds off, and keep asking the next question. It'll introduce you to names, places, and questions you didn't know existed. You can find everything I do at jillfromthenorthwoods.com, and you can reach me directly at jill@startwithsmallsteps.com. --- **A note on this podcast:** I'm not a software developer or an AI professional, just someone who uses these tools every day and shares what's working for me. Test anything I mention against your own situation before you rely on it. TIMESTAMPS 00:00 Using AI to explore your hometown 02:19 The first question 02:58 Iron ore and who founded Marquette 05:24 Why is it called Marquette? 09:38 The Lower Harbor ore docks 11:01 The dock that washed away 17:32 Building the walking tour 20:36 Verify what AI tells you 22:16 Lunch: the Upper Peninsula pasty 26:09 Ask AI what you're missing

  4. Sep 30

    AI Shopping Isn't Magic, But It's Close

    Online shopping gives us enormous selection, but selection isn't the same thing as clarity. This episode is all about how AI changes the shopping conversation, not by magically finding the perfect thing, but by listening to your whole problem the way a search box never could. **When "I Liked It Last Time" Stops Working** Shoe companies redesign their shoes. Hiking pants get discontinued. The old trick of just buying the same thing again falls apart the moment a product changes or disappears, and that's exactly where AI earns its keep. **Describing the Experience, Not Just the Product** Instead of searching for a shoe brand, you can describe what you actually liked about the old one, wide toe box, moderate cushioning, low heel drop, and ask AI to translate that into what's available now. It turns shopping into a translation problem instead of a search problem. **Finding a Chair Built for a Very Specific Body** I talk through how I used AI to find a chair for my short legs and short trunk-to-knee measurement, right down to it telling me exactly what to measure on myself before recommending five real options. **A Camera Upgrade Worth Actually Making** As a birdwatcher, I asked AI whether a newer version of my camera was worth it. It read through specs and reviews I couldn't find on my own and pointed to the one genuine upgrade that mattered for bird photography: subject tracking. **AI Asking You Questions Back** One of the most useful parts of shopping with AI is when it asks you questions instead of just answering yours: why do you want this, what isn't your current one doing for you. That's often where the real requirements show up. **Grocery Shopping and Food Substitutions** From tracing a friend's heartburn back to her coffee, to finding pepper substitutes for fajitas, AI can turn grocery shopping into an experiment instead of a guessing game. This podcast is for entertainment and educational purposes only. I'm not a software developer or AI professional, just someone who uses these tools daily and shares what I've learned. Find all of Jill's podcasts and videos at jillfromthenorthwoods.com. Questions or topic requests? Email jill@startwithsmallsteps.com. TIMESTAMPS 00:00 When "I Liked It Last Time" Stops Working 03:36 Describing the Experience, Not Just the Product 06:29 Finding a Chair Built for a Very Specific Body 07:48 A Camera Upgrade Worth Actually Making 10:12 AI Asking You Questions Back 12:20 Grocery Shopping and Food Substitutions 16:09 Making It Work for Clothes Shopping Too

  5. Sep 23

    Ask AI Before You Upgrade or Subscribe

    # Ask AI Before You Upgrade I got an upgrade email this week for photo editing software I already own, and instead of asking whether the new version was any good, I asked AI a completely different question: do I actually need this? **Ask "Is This For Me," Not "Is This Good"** Almost any piece of software is well-made. The real question is whether its new features match how you actually use it. I compared a new release against my own two specific use cases, cleaning up bad bird photos and prettying up sunset shots, instead of asking a generic "should I upgrade" question, and the answer came back no. **The Best Product Isn't Always the Best for You** The best professional video editor is wrong for someone who just wants a 30-second dog video, and the best backpacking boots are overkill for someone walking a paved trail. AI is good at translating a features list into "will this actually change your life," which a search engine and a comparison chart can't do. **Reading Subscription Tiers Through Your Own Life** Comparison charts tell you what each tier includes, but not which of those things you'll actually use. I described my real workflow to AI and let it sort the plans by relevance, sometimes landing on the cheapest tier, sometimes realizing the expensive one actually saves real time. **The "Beginner's Tax" on New Hobbies** Starting something new, like a Cricut crafting machine, tempts you to buy every accessory available. AI can help separate what a true beginner needs from what's aimed at advanced users, and can flag features you already own somewhere else entirely. **Running a Subscription Audit** I walked AI through my actual software subscriptions against what I really use, which led me to cancel a calendar app subscription once I realized Apple's built-in calendar already did the job. Sometimes the answer AI gives you is simply: you already own this. The real shift isn't that AI makes things cheaper. It's that it can ask "what problem are you actually trying to solve" instead of trying to sell you something. Before your next upgrade or subscription, try handing AI your actual use case and your budget, and see what it tells you to skip. You can find everything I do at jillfromthenorthwoods.com, and you can reach me directly at jill@startwithsmallsteps.com. --- **A note on this podcast:** I'm not a software developer or an AI professional, just someone who uses these tools every day and shares what's working for me. Test anything I mention against your own situation before you rely on it. TIMESTAMPS 00:00 The software upgrade email 01:29 Asking "do I need this," not "is it good" 05:29 The best product isn't the best for you 08:26 Reading subscription tiers through your own life 12:21 A real example: choosing a website plan 17:16 The Cricut trap and the "beginner's tax" 23:07 Why AI beats upselling 26:36 Assigning AI a skeptical role on purpose 28:34 Running a full subscription audit 32:01 The cost of complexity, and the closing takeaway

  6. Sep 16

    Do You Need a Paid AI Subscription?

    Everyone wants to ask "which AI subscription should I buy?" I think that's the wrong first question. The right one is: what did the free version actually stop me from doing? This episode walks through how to figure that out before you hand over $20 a month to anyone. TRY FREE FIRST, ON PURPOSE Spend a week using a free AI tool on real tasks you'd normally do, gardening spreadsheets, birding lists, rough retirement math (no account numbers, just ballpark thinking). Notice exactly where you hit a wall. THE ONLY QUESTION THAT MATTERS Not "which AI should I subscribe to," but "what did free prevent me from doing?" If the answer at the end of the week is nothing, you've saved yourself a subscription. WHERE FREE TENDS TO BREAK DOWN Usage limits that cut you off mid-project, features locked behind a paywall like larger projects or deep research, or a specific integration that would save you real hours every week. Those are legitimate reasons to upgrade. "Someone on YouTube said so" is not. HOW THE MODELS DIFFER RIGHT NOW ChatGPT tends to win on personalization, image generation, and third-party integrations. Claude tends to win on writing quality but has tighter free-tier limits. Perplexity has a reputation for strong sourcing. Each has real free-tier limitations worth testing for yourself, since it changes constantly. A REAL EXAMPLE OF WASTED MONEY A friend bought a full year of an AI subscription and realized afterward she didn't write professional documents, didn't code, and wasn't using it for anything a free tier couldn't already do. WHEN IT BECOMES OBVIOUS YOU NEED PAID Running multiple podcasts made a paid account an easy call: grouped projects for thumbnail work, heavier research needs, and specific automations that save real time each week. The bottom line: don't subscribe because you're worried about missing out. Subscribe because you can name the exact wall you keep hitting. If you've got a story about deciding between free and paid AI, I'd love to hear it. Email me at northwoodsjill@fastmail.com, or find everything at jillfromthenorthwoods.com. Jill’s Links https://jillfromthenorthwoods.com/ - Find my podcasts, videos, downloads and ways to contact me https://www.buymeacoffee.com/smallstepspod https://x.com/NorthWoodsJill Email the podcast at jill@startwithsmallsteps.com By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and educational purposes only. I am not a software developer, data scientist, or AI professional. Any tips, tools, or suggestions offered should not be considered a substitute for professional technical advice. AI tools and platforms change frequently — always verify current features, pricing, and terms directly with the providers. You are solely responsible for any decisions or actions you take based on this content.

  7. Sep 9

    My Real AI Workflow for Books, Podcasts, and Saved Articles

    I consume a genuinely ridiculous amount of content, books, podcasts, videos, articles I've been saving for twenty plus years into a filing cabinet in my basement that I haven't opened in probably as long. For most of my life, the weak link in all of that consuming was always me: I'd underline something, screenshot a quote, tell myself I'd come back to it, and then watch it disappear into the enormous warehouse of things I once found interesting. This episode is about how AI changed that, not by writing content for me, but by helping me actually use everything I take in. The old model of consuming content was broken by design Books, podcasts, notes, saved articles, they all sat in a system (my filing cabinet, in my case) waiting to be remembered and retrieved, and most of it never was. I moved from Pocket to Notion a while back, and now every transcript and saved article lands in one searchable place instead of a drawer I forget exists. A real example, fact checking a nutrition article while mowing the lawn I ran a health article's advice past AI and asked which parts were actually backed by evidence versus which weren't. It agreed on some things (choline from eggs, for instance) and helped me push back on claims that didn't have real research behind them, including asking for sources when something felt shaky. A real example, turning career advice into something personal I listened to Mel Robbins interview Carla Harris on career advice by decade of life, then had AI pull out what actually applied to me at my age and stage, including some hard self reflection about growing up needing to please other people rather than asking myself what I actually wanted. Why this makes creators better instead of making everyone the same The fear that AI will homogenize content is real if you use it lazily, ask ten people to "write a podcast about productivity" and you get ten forgettable scripts. But the better use starts before the writing: what irritated you, what you noticed, what connected to something you've been thinking about for months. That's the part AI can't generate on its own, it can only help you dig it out. AI as a sparring partner, not a ghostwriter Because everything I save lives in one system now, AI can connect a career podcast to my own ikigai episode from months ago, warn me when a draft has an edge I don't actually want, or collapse a dozen saved stretching articles into one usable routine, all without me having to remember any of it existed. What I actually want from AI as a creator Not speed, and not friction free content. I want something that helps me notice more, question more, and remember what I already know, so that by the time I turn on a microphone, I have something that's actually mine to say. If you're a content hungry person who's tried and failed to build a "system" for everything you read and listen to, this one's for you. I'd love to hear how you're using AI to think, not just to produce, send me your version. 00:00 Intro, twenty years of saved articles I never look at 01:59 Why the old model of consuming content breaks down 03:28 Moving from Pocket to Notion, building a real system 04:27 What AI actually adds beyond summarizing 06:58 Case study, fact checking a nutrition article and a career podcast 11:53 Why bringing yourself to the process is what prevents generic content 16:21 Connecting new ideas to old ones, the ikigai example 21:19 Turning saved articles into one usable stretching routine 22:21 How AI helped me notice my own "harsh edge" while writing 26:22 Why not everything needs to become content, wrap up northwoodsjill@fastmail.com jillfromthenorthwoods.com Jill’s Links https://jillfromthenorthwoods.com/ - Find my podcasts, videos, downloads and ways to contact me https://www.buymeacoffee.com/smallstepspod https://x.com/NorthWoodsJill Email the podcast at jill@startwithsmallsteps.com By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and educational purposes only. I am not a software developer, data scientist, or AI professional. Any tips, tools, or suggestions offered should not be considered a substitute for professional technical advice. AI tools and platforms change frequently — always verify current features, pricing, and terms directly with the providers. You are solely responsible for any decisions or actions you take based on this content.

  8. Sep 2

    23 - The Three Questions I Ask Before Publishing Anything AI Wrote

    A few weeks ago an AI tool handed me back a paragraph that sounded completely confident, totally polished, and was just wrong. Not obviously wrong, the kind of wrong that slides right past you if you’re in a hurry. That moment is basically this whole episode. AI is a genuinely useful tool, but the same thing that makes it fast and confident is exactly what makes it dangerous to lean on without checking. Logistics AI has always done well. Recommendation engines, calendar assistance, first-pass drafts, these are the same category as auto pay or a calendar reminder: friction removed, nothing lost. AI is genuinely great at the blank page problem, at restructuring a messy voice memo, at comparing two spreadsheets, at giving you a first draft of show notes. Where AI is different from a calendar reminder. A calendar reminder never tries to be right about facts. It just tells you the time. AI will state a false thing in the exact same confident tone as a true one. I’ve caught it misidentifying birds on my nature podcast and inventing plausible-sounding history on my Bible podcast. Unlike a human expert, who’ll tell you when they’re not sure, AI states everything with equal confidence unless you specifically prompt it not to. The Dome of the Rock thumbnail story. I asked for an image of Jesus looking over Jerusalem, and AI put a mosque that wasn’t built until roughly 600 years later into the scene. It’s a good drafting partner, not a source of information, and that distinction matters. The context problem. I share a story about someone who had AI rewrite an internal email for a different audience without checking it, and the tool didn’t know which details didn’t apply to the new group. The email went out confused, and leadership had to send a correction. The failure wasn’t really AI being wrong, it was nobody reviewing the output before it went out under someone’s name. Three questions before you publish anything AI touched. Can I verify this myself, especially any hard fact, date, or name? Does it still sound like me, or has it turned into smoothed-out generic internet voice? And would I be comfortable if someone traced this sentence back to me? I tell the story of an early Substack draft where AI invented a detail in a personal story about my dad during a snowstorm when I was eleven. No one else would have caught it. I did, because it was my story. How I actually use it. I start with my own draft, let AI suggest structure and flow, then rewrite it myself, then let it help with grammar. Different creators layer it differently, but the point is the same: your voice in your own project has to stay yours. One resource: look up “automation bias,” the research term for our tendency to over-trust confident-sounding systems. Jill’s Links https://jillfromthenorthwoods.com/ - Find my podcasts, videos, downloads and ways to contact me https://www.buymeacoffee.com/smallstepspod https://x.com/NorthWoodsJill Email the podcast at jill@startwithsmallsteps.com By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and educational purposes only. I am not a software developer, data scientist, or AI professional. Any tips, tools, or suggestions offered should not be considered a substitute for professional technical advice. AI tools and platforms change frequently — always verify current features, pricing, and terms directly with the providers. You are solely responsible for any decisions or actions you take based on this content.

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About

AI isn't just a search engine. It can help you think through a hard decision, organize your house, plan your retirement, and sometimes — if you let it — say exactly what you needed to hear. Small Steps with AI is hosted by Jill from the Northwoods, a real person figuring out how this technology fits into real life. No coding. No hype. Just small steps.

Information

  • Creator
    Jill McKinley
  • Years Active
    2026
  • Episodes
    30
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Jill McKinley
  • Show Website
    Small Steps with AI

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