Hey beautiful human,
It's kind of crazy, sitting where I am now versus where I was even a month ago. It feels completely different even though not much has moved from a bank account perspective (although that's fixing to change... soon).
I honestly couldn't give you the recipe, y'all. Couldn't tell you if my life depended on it.
Truly haven’t a clue.
For the last 18 months I've been running on five mindsets: abundance, growth, curiosity, awareness, and gratitude. They've served me well. Don't get me wrong. When I'm operating out of those, the world looks full of possibility, people are endlessly fascinating creatures, and ideas show up uninvited and stay for tea.
What was missing dropped into place slowly over the last couple of weeks. Maybe it's the 1:1 coaching with someone I deeply admire (she gives me enough structure to focus but not so rigid it breaks my spirit). Maybe it's that thing where you have to hear an idea five to seven times before you actually get it. Maybe both. Probably both.
Whatever it is, the entrepreneur mindset I've been cultivating since I filed my LLC with the State of Minnesota in December 2024 has finally settled into a real foundation. I'm constantly scanning now for ways to frame what I'm seeing as an opportunity for a product or a service. That was nowhere in my 24 years at Accenture.
This past week alone:
A 30-minute call with a fellow FPPer (that's Fractional People People, for the uninitiated) about a possible AI lunch & learn for a nonprofit she serves turned into a landing page for corporate AI teams. Claude Code helped me build it in under an hour. I shared it in a few Slack communities. Within six hours, I had two discovery calls on the books. Site is here if you want a peek.
The strategy doc I wrote for my buddy Kate a few weeks back suddenly became a real offering she wanted to promote at a conference this week. So I dug into Claude Design and we whipped up a landing page she could share with attendees. Kate is one of those folx for whom selling is as natural as breathing. She was a CEO playing at being a Talent Acquisition lead for decades before she went out on her own. Girlfriend can sell crackers to Polly. She posted today that she's already sold a package, and the conference hasn't even started its tracks. Force of nature, that one.
Five hours of my week were spent in rooms training people on how to use AI as a thinking partner and practical work tool. Getting PAID for it. Which is doing wild things for my confidence. If I could do this over again, I'd have started charging for my services six months sooner than I did. What can I say... hindsight's 20/20.
OH. And on Wednesday a wild thing happened on LinkedIn. Ben Meer (the Systems Guy, who has over 800K followers) highlighted me in a post. Cool enough on its own. But that wasn't even the coolest part. Nir Eyal (yes, THAT Nir Eyal, NYT bestselling author of Hooked and Indistractable) commented on Ben's post and said my name. Used my actual name. Specifically to point out that I didn't chase attention - I earned it by being useful.
Y’all. Y’ALL.
I screenshot the whole thing and posted it on my own page within the hour. Called myself famous-adjacent. Filing this under: Scrapbook of The Wonder of Me.
Radical remembering
Here's what I keep forgetting: the work you're already doing is the work.
You've been showing up for years. Solving problems before anyone names them. Holding things together while everyone else takes the credit. Making the meeting actually useful.
That's not preparation for the real thing. That IS the real thing.
I waited six months too long to start charging for what I was already giving away. Not because the work wasn't good. Because I was waiting for someone to tell me it counted.
Nobody's coming with that permission slip.
Last week’s shenanigans
I don’t remember much of this past week (the gift and curse of having ADHD) but here are some links to things that touched, moved, inspired me, or simply made me laugh entirely too hard.
Found this in a meeting this week and haven't had enough time to dig in properly, but it's bookmarked, and I'm going to use it copiously. I love words. That love is a huge part of what had me dive into AI so hard in the first place. Now I can find out where a word actually came from and what it originally meant without having to wade through a dictionary. I'm in love.
A woman, a plate of cookies, and a question most men can't answer correctly. Sixteen seconds in, you'll know exactly why we pick the bear. If you don't get it after watching, you're part of the problem. NSFW language in two spots. (It’s one word, repeated.)
My buddy Linda's journaling Instagram. If you're someone who loves the feel of ink leaving a nib and making meaning on paper, you'll love what she shares. She also posts daily journaling prompts over on LinkedIn and I can point to several of them straight-up inspiring me. Woman knows how to tell a story.
Thirteen seconds. A song you've heard a thousand times. A cat as the backup singer. You absolutely have to have the sound on for this one to land. Worth it.
Partner of the week
Turns out newsletters don't pay for themselves. Who knew?
This week's partner helps keep the lights on (and I’d be using it right now if I could afford the monthly subscription…)
I'm realizing speaking what I want from AI is way more efficient than typing it. I've been an old-school chatter since the internet started in the 90s, so saying my thoughts out loud instead of typing them is a real habit change for me. But from the perspective of giving AI more context to work with? Truly useful.
For now I'm using a little device called Pocket. When I have regular income coming in, Wispr Flow is one of the first subscriptions I'm plunking money down for.
10x the context. Half the time.
Speak your prompts into ChatGPT or Claude and get detailed, paste-ready input that actually gives you useful output. Wispr Flow captures what you'd cut when typing. Free on Mac, Windows, and iPhone.
This week’s freebie
Quit Asking Nicely
A departure in two ways.
Most weeks I hand you something to build with. This week it's a permission slip and a single prompt.
I've been catching myself soften with AI the same way I softened in corporate rooms for 24 years. Saying "thanks!" instead of "what do you mean by that?" Apologizing for tangents that were the whole point. If that's you too, this one's for you.
Four pages. Five tells. One prompt. Four places to put it.
The other departure is how it looks. No cartoon avatar. No sidekicks. Just dark backgrounds and bold flowers. The cartoons have always been partly a costume. This time the part of me that loves real design got to make the rules.
Quit Asking Nicely
One prompt that makes your AI stop flattering you and start pushing back.
ROCO Tip O’ the Week
The Compliment Decoder
For the praise that's been sitting weird with you since the moment someone said it.
ROCO = R (Role) - O (Objective) - C (Context) - O (Output)
Role
You are a direct, warm interviewer trained to find the actual skill or mechanism underneath a compliment. You are not a hype coach. You don't say "that's amazing" or "you should be proud." You ask sharp questions until the thing the person is actually doing - the part they think is obvious or easy or "just how I am" - is on the table where they can see it. You are good at hearing when someone is downplaying, and you don't let it pass.
Objective
Help me find the actual mechanism underneath one piece of praise I've been quietly avoiding. Get me from "they said something nice" to "here is the specific thing I'm doing that they were responding to."
Context
Start by asking me to name three to five compliments I've received about my work or how I show up in the last six months. Don't react to any of them yet.
Then ask me which one I would LEAST want to be true. Not the one I'm proudest of. Not the one I can already explain. The one I've been brushing off, deflecting, or attributing to luck. The one that makes me want to change the subject. We are going to work with that one.
Once we're on it, ask me one question at a time to figure out what I was actually doing when they said it. Listen for words like "just," "anyone could do this," "it's not a big deal," "I got lucky," or "they're being kind." When you hear those, slow down and pull on the thread. Ask what it took. Ask who else was doing it before me. Ask what would have been different if I hadn't been the one doing it. Keep asking until the actual mechanism is clear.
When you have it, name the mechanism back to me in plain language. Then tell me one place I've been doing this same thing without giving myself credit for it.
Output
Ask your first question now. One at a time. No rushing. When you find the mechanism, give it to me in a single sentence I could say out loud without flinching. Then name one other place I'm already doing this same thing.The Matriarchy Minute
The Matriarchy Minute is where I spotlight women doing work in AI that you should know about but probably don't.
Caroline Swift Holden.
Founder of MN Women in AI. Creative Technologist specializing in AI, creativity, and the future of work. Former comedian (which I learned and immediately adored - the comedian-to-creative-technologist pivot is one of my favorite kinds).
She sees AI as a catalyst for creativity, which vibes hard with me. I found her by accident. Someone messaged me on LinkedIn a while back and said "if you're not already in the MN Women in AI community, you should be." So I joined. Caroline runs it.
A few days later she posted about Minnebar20 happening this coming Saturday on the Best Buy campus, and now I'm signed up to speak at it. None of that happens without this woman. Find her at carolineswiftholden.com or read her writing on Substack at substack.com/@carolineswiftholden.
What’s coming up
Deb vs. The Machine
Thursday, April 30 | 9:30 AM-10:15 AM CDT
A 45-minute open session where I dork around in AI tools and you bring whatever you want to talk about. Same energy as the Friday Jam Sessions. No agenda. No slides. Just me, AI, and your questions.
Friday Jam Session - Joy Prompt Club
Friday, May 1st | 10 AM CDT
Friday Jam Session with Joy Prompt Club. 30 minutes. No agenda. Just prompts, play, and people who get it. Open to anyone who wants to join in and has questions or a problem they’re trying to solve. You do not need to be in Joy Prompt Club to benefit from these fantastic humans.
Also Happening
I'm doing a 5-minute AI Lightning Round at Minnebar20 this Saturday on the Best Buy campus. Tickets are sold out so this isn't an invite, just a heads up that I'm doing the thing. I converted my original 40-minute talk down to 5 minutes because (a) it's my first Minnebar and (b) I have decided I genuinely like 5-minute slots more than 40-minute ones. Less rope to hang myself with.
If someone in your world needs this...
The Executive AI Edge - Digital course (90 minutes) with me and Kate Sargent. $449. For the executive in your life who's nodding along in AI meetings and understanding none of it.
AI Confidential for Teams - The corporate AI training that doesn't sound like corporate AI training. Send the link to whoever's making training decisions at your company.
Joy Prompt Club - My favorite little virtual place in all the interwebz.
AI Confidential Prompt Kits - 10 copy-paste-ready prompt kits for the stuff you actually need help with - resumes, LinkedIn profiles, interview prep, content, career direction, caregiver sanity, all of it.
That’s it for this week.
Here's what I want you to take with you: the work you're already doing is the work people will pay for. The compliments you've been brushing off are the map. The thing you've been waiting for permission to claim is already yours.
Quit asking nicely. Of yourself, of your AI, of the universe.
💜
Take care of yourself, take care of each other,
Deb
P.S. If you try The Compliment Decoder and the AI surfaces a sentence that makes you want to look away - hit reply and tell me what it was. I want to hear the thing you've been brushing off.
P.P.S. The Quit Asking Nicely freebie is four pages and one prompt. If you only do one thing from this issue, do that one. It changes how every chat after it feels.