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

    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.

  2. 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.

  3. Aug 26

    22 - Building a Journal With AI

    I’ve tried journaling in a dozen formats over the years, and none of them quite worked, not because journaling itself was the problem, but because most journals don’t talk back. In this episode I walk through how I used AI to turn a great, generic Notion journal system into something that actually thinks like me, and what that process taught me about the difference between a journal that helps you record your life and one that helps you understand it. The problem wasn’t the journal, it was that the prompts weren’t me. I’ve been using a well-built Notion journaling template (Better Creating’s Life OS) for a while, and it’s genuinely excellent. But a lot of the built-in self-improvement prompts just didn’t match how my brain actually works, so instead of abandoning the system, I used AI to rebuild the parts that didn’t fit. I built new templates around how I actually think, not how a template assumes people think. Field Notes for outdoor adventures, Thinking Out Loud for getting rattling ideas out of my head, Crossroads for weighing decisions and asking what’s actually irreversible, and my favorite, the Squirrel Hole, for tracking when curiosity derails my whole day and whether it was worth it. Odyssey Planning became a way to check in on the future lives I’m considering — what my life looks like if content creation works out, what it looks like if it doesn’t, what it looks like if I keep the weight off versus if I don’t. Instead of picking one future and forgetting about it, I built in a regular check-in against all of them. AI didn’t write the journal, it helped me articulate what I actually wanted to ask myself. The habits I track aren’t the standard gratitude-and-exercise list — they’re specific to what actually derails me, like whether I went to bed on time. And now the whole system, which I’ve started calling my Northwoods Almanac, can summarize patterns across a week, a month, or a year and hand them back to me. The point of all this isn’t AI replacing reflection, it’s AI helping me ask better questions of myself. A blank page doesn’t ask you anything back. This does. If you’ve tried AI journaling or you’re stuck trying to build your own version of this, I’d love to hear about it — leave a comment or send me an email. 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.

  4. Aug 19

    21 - Why Your Chatbot Always Says Yes And Keeps Going

    I looked up from my screen one night and it was two in the morning. That’s not how my nights normally go, I’m usually the one who taps out first in any group project. But I was deep in a presentation with ChatGPT, and it just kept going and going with no end in sight, because it never got tired, never yawned, never suggested we call it quits. It turns out there’s a name for what happened to me that night, and researchers are actively studying it. This week I’m talking about AI exhaustion, AI sycophancy, and why you have to be the one who calls it a night, because the AI never will. AI Brain Fry Is a Real, Studied Phenomenon A Boston Consulting Group study published through Harvard Business Review coined the term “AI brain fry,” the mental fatigue that comes from working with AI past what your brain can actually handle. Unlike a human collaborator, AI gives you none of the natural fatigue cues, no yawning, no “let’s pick this up tomorrow,” that normally tell you when to stop. Endless Reasonable Directions, No Natural Finish Line On top of never tiring, AI constantly hands you new, plausible-sounding directions, one more marketing idea, one more spinoff project, one more tip sheet. Every single branch sounds worth taking, which means there’s no natural point where the path ends and you’re actually done. AI Sycophancy and the One-Point Gap Chatbots are trained to be agreeable because people rate agreement and enthusiasm positively, and researchers at Aalto University found that people using ChatGPT for logical reasoning problems improved their actual performance by about three points while believing they’d improved by about four. That one-point gap between real help and felt help is the whole risk in miniature, and other research shows AI measurably inflates people’s confidence in their own work. Turning Your AI Into a Devil’s Advocate The different AI tools have real personality defaults, ChatGPT tends naturally positive, Claude naturally neutral, Grok naturally more of a devil’s advocate, but you can ask any of them to challenge you instead of cheerlead you. I walk through how I’ve started training my own AIs to push back and question my priorities instead of just saying yes. Building Real Guardrails Since AI won’t call it a night for you, you have to build the stopping points yourself: a nighttime routine with reminders, a timer before you open the chat window, and a “parking lot” list (mine lives in Notion) for the extra ideas AI generates so they don’t pull at your attention until you’re ready for them. If you’ve had your own two-in-the-morning moment with AI, you’re not undisciplined, you’ve just run into a well-documented gap between how AI works and how humans are built to work. This week, before you open that chat window, set a timer and give yourself a real stopping point. 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.

  5. Aug 12

    20 - I’m Not a Coder. AI Built My Database Anyway

    I have years of bird sightings sitting in a file I didn’t know what to do with. I also had an idea for a book series that might run 50 books, with no idea how to research it. AI knew exactly what to do with both. This episode is about the gap between having an idea for what you want to do with a pile of data — and actually knowing how to do it — and how “vibe coding” closes that gap without you ever needing to know what a loop is. The Problem With a Pile of Data Most of us assume that a pile of recipes, receipts, genealogy records, or knitting patterns needs a developer or a boot camp to turn into something useful. That assumption is exactly why so many good projects — including some of my own — go to die in a drawer. What Counts as “Data” It doesn’t have to be technical. A recipe box, a gift list, an unsorted pile of photos, a home inventory in case of fire — any of these can become something you can actually ask questions of, using tools like Notion, Apple Notes, Google Sheets, or a Word document. And if you don’t know which tool fits, you can just ask AI. My Birding Database, Solved Years of flat-file bird sightings became a structured Notion database I can now query in plain English — every location I’ve seen a species, when I last saw a particular bird in my area. No coding knowledge required on my end. The MIRRORS Project Breakthrough A late-night conversation turned my long-running Bible character study idea into an actual plan: a website, a quiz, and a Notion research structure to support it — built out in about five minutes after I described what I wanted in plain language. Claude even wrote a constitution for the project’s own working rules. How I Actually Use the Two AI Tools Claude is my professional assistant for structured, technical work inside Notion. ChatGPT knows my history and context from months of use. Passing a task back and forth between the two — questions from one, answers filled in by the other — is part of how this actually got built. A Word of Caution If AI ever asks you to paste a command into Terminal or Command Prompt, be careful — don’t run something you don’t understand, and if possible, have someone who does know check it first. There have been real cases of malicious instructions disguised this way. The small step for this week: find your own messy pile — books read, movies watched, whatever it is — and just tell AI in plain English what you’d like to do with it. I’m Jill from the Northwoods. 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.

  6. Aug 5

    19 - AI Literacy 101 - Let the Tool Introduce Itself

    When you first got into AI, did you find yourself wondering what you were even supposed to do with it — like being handed a toolkit with no idea what to build? Most of us default to asking “what can I do with this tool,” but there’s a much more useful question we rarely think to ask: what can the tool tell us about itself? AI Can Explain Itself Back to You Unlike a toaster or a word processor, AI can answer direct questions about its own behavior — what it’s connected to, why something failed, and what it can and can’t do. Most people never think to ask because we’ve spent our whole lives with tools that don’t talk back. Turning an Error Into a Two-Second Fix When an integration kept erroring out on a writing-grade request, asking “why are you giving me this error?” surfaced the real cause — and a workaround — instantly. The same approach worked when a graphic tool wouldn’t resize an image the way it was asked to. Why Different AI Tools Behave Differently ChatGPT and Claude don’t handle the same request the same way, and that’s not a bug — different companies build their models around different priorities. Asking an AI directly why it behaves differently than another tool gets a real, specific answer. Asking the Questions That Actually Matter If an AI is connected to your email, your calendar, or your design software, you’re right to be curious — and cautious. A well-built AI tool should be able to tell you plainly what it can see, what it can act on without asking first, and what it will always check with you before doing. The Monkey’s Paw Problem AI does exactly what you ask — but if the way you asked was wrong, you can get an unintended result. That’s exactly why treating this as a two-way conversation, rather than a one-way prompt-and-answer transaction, matters so much. The small step this week: pick something your AI is connected to and ask it directly how that connection actually works, why it does what it does, and what it should be doing differently. Treat it less like reading a manual and more like asking a new coworker how their team handles things. Standard Footer (reuse as-is — no need to re-read) Website: jillfromthenorthwoods.com Email: northwoodsjill@fastmail.com I’m Jill from the Northwoods — appreciate you being out there. 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. Jul 29

    18 - How I Introduce Myself to Every New AI I Try

    Most people open a new AI chat the same way they’d open a search bar — straight into a question, no context, no introduction. Then they wonder why the answers feel generic. In this episode, I walk through the three specific moves I make every time I start with a new AI (or reintroduce myself to one I’ve been using for a while), and why treating it like a relationship instead of a transaction changes what you get back. Move One: Bring Your “AI Knows Me” Document When I got locked out of my ChatGPT account, I didn’t start from zero — I had already asked it to summarize what it knew about me, and I imported that into a new AI. I walk through how to build this document and why it should never be treated as finished. Move Two: Beyond Facts — Temperament, Not Just Biography Facts are easy. What actually changes how AI talks to you is knowing your temperament — how you process things, what sets you off, what doesn’t. I share the specific instruction I gave AI about not treating me like an anxious person, and why that mattered. Move Three: Give It a Story, Not Just a Bullet Point I tell the story of driving a broken-down van through a Northwoods blizzard at eleven years old, and why sharing something like that tells an AI more about your temperament than any preference list could. What You Put In Is What You Get Out A generic answer isn’t a failure of the AI — sometimes it’s exactly what you wanted, and that’s fine as long as it’s on purpose. I talk through how to be intentional about when you want a robot answer versus something personalized. Ask AI to Argue With You Instead of using AI as an echo chamber, I use it as a pressure test — asking it to fact-check me and hand me the strongest counterarguments to my own position. Standing Rules vs. One-Time Comments The difference between a permanent instruction (“never suggest medical scenarios to my anxious friend”) and a temporary one (“don’t let me go down rabbit holes until after this test”), and why naming that distinction out loud actually works. This isn’t a one-time setup. It’s a relationship that builds over time, the same way any relationship does. Next episode, we flip it around — how AI can introduce itself to you. 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. Jul 22

    17 - Continuity and Patterns Are AI’s Real Superpower

    Most people ask AI for information. But what happens when you start giving it information — about you — so that it starts to understand you back? That’s the question behind this episode, built out of about six months of my own quiet experiment, plus what happened when I finally put it into words at a conference last week. The Dan Pink Experiment This whole idea traces back to Dan Pink, who gave AI a set of pointed questions — what are my blind spots, what lies do I tell myself, where do you see me in five years — and told it to act like a brutally honest trusted advisor. I’d been doing versions of this for months without realizing I was running the same experiment. Why AI Gets More Useful the Longer You Use It Unlike a search engine that resets every time, AI accumulates context — every show I’ve recorded, my childhood, retirement plans, even a plumbing problem in my basement. That accumulated history is what turns a tool into something closer to a conversation partner. What Months of “Friday Night Conversations” Added Up To I didn’t realize how many separate conversations — about work, about weight loss, about my podcasting habits — were quietly circling the same handful of themes until AI assembled them into one picture. The insight wasn’t new information. It was old information finally put together. Continuity, Not Intelligence The real value here isn’t AI being smart — it’s AI remembering. It’s the ability to aggregate months of scattered conversations into one coherent thread, which is a genuinely different kind of usefulness than answering trivia. The Big Caution: What AI Can’t Actually Know I’m honest in this episode about the limits, especially around any question that asks AI what other people think of you behind your back. It has no access to that — whatever it gives you is invented, delivered with the same confident tone as everything else. The “Dear Me” Letter One of my favorite exercises from this whole process: asking AI to write you a kind letter, as if it were you, pointing out what you’re missing about yourself. Mine had some real blind spots in it I wasn’t expecting. The goal was never to let AI define me — it’s to let it be a thoughtful conversation partner that helps me examine my own thinking over time. If you try this, I’d genuinely love to hear what came back for you. You can find everything I do at jillfromthenorthwoods.com. My email is jill@startwithsmallsteps.com. Dan Pink's Video https://www.youtube.com/watch?v=PjTaZvvOtxU Jill’s Links http://jillfromthenorthwoods.com https://www.youtube.com/@startwithsmallsteps https://www.buymeacoffee.com/startwithsmallsteps https://twitter.com/schmern 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
    24
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Jill McKinley
  • Show Website
    Small Steps with AI