Hey beautiful human,
It's been a fun week.
Fun as in actually fun. And also fun as in "well. THAT was fun," said flatly, into the middle distance, by a woman who did not enjoy herself.
Both. All week.
Tuesday night I was up too late clicking around my own LinkedIn like a weirdo, and I landed on a post I wrote in July 2024 about being unemployed.
22,165 people saw that one.
I remember writing it. I remember exactly how my stomach felt.
Two days later I'm on a live with Emily Worden and 141 people are in the room asking questions.
Same woman. Two years apart.
I don't have one tidy feeling about that. I have about nine.
The business is finally clicking. People get what I do and they're buying it, which took forever and which I had honestly stopped expecting.
And right as it clicks, I'm working out that some of the work I've been doing is the wrong work for me.
One-on-one coaching. Some of those hours are FANTASTIC. Both of us going, ideas flying, and I walk out with more than I walked in with.
And some of them I'm sitting across from a person who wants it handed to them, finished. They booked the hour, they showed up, and now apparently I perform a miracle while they watch.
I can't. I'm not up for it.
Ten years ago, maybe...
And I don't know which one I've got until I'm twenty minutes in. Same booking. Same hour. Same me. One version has me buzzing all afternoon. The other leaves me wrung out like a dishrag somebody left in the sink.
Then Friday.
Jam Session in Joy Prompt Club. Six women. Scheduled for 45 minutes, ran 61, and I don't think a single person noticed.
(I keep almost making it an official hour and I keep not doing it. Something happens when people see 60 minutes on an invite that doesn't happen at 45. And I want that door staying easy. You don't have to come. You don't have to stay. You don't have to say a word. Camera off, in the back, lurking - that counts. That IS participating.)
You know that thing where you picture your future life? Some version of it you can almost see, and you think about how good it's going to feel to finally be standing in it?
Friday I was standing in it while it was happening.
On paper it's a call about AI. Which tool for what. Why the chat gets dumber the longer it runs. How to make it sound like you.
Underneath it was six women who got to put the mask down.
You know the mask. The professional one. The one that goes on before you go anywhere.
For an hour nobody had to wear it. Nobody had to explain herself. Nobody had to translate.
They just got it.
They got the extra labor we've been carrying our whole lives. Some people don't even see it. The rest of us feel the weight of it every single day.
All the unsaid things everybody treats as normal, that cost us in a hundred small ways.
Bloodletting in itty bitty bits. Every day. More blood than the monthly kind we were told was just our lot.
So I'm doing less one-on-one and more of this.
141 people Thursday. 6 on Friday. I had more energy at the end of both than I had going in.
One person across a table waiting to be fixed? I need a nap and a dark room.
Radical Remembering
Here's what I keep forgetting: I never wrote any of it down.
Every week now I talk to women twenty years in, sometimes thirty. They did it the way we were all told to do it. Stayed through the restructures. Trained the person who got promoted over them, and then wrote her a nice note about it. Extra hours nobody logged anywhere.
Then the contract changed and nobody sent a memo. Loyalty stopped counting. Quietly good stopped counting. Now you have to justify your value and your existence, out loud, to strangers, over and over.
The ones out looking just found out first. A desk is not the shelter it used to be, and neither is a retainer, or a roster of clients, or years of goodwill.
We all freeze at the same question. Nobody ever asked us to keep a list. Saying it out loud felt like bragging, and we were trained out of bragging before we were twelve.
The work is still ours. Writing it down is the part we get to start today.
Joy Prompt Club
In da club
Joy Prompt Club
The room from earlier in this email.
Three prompts a week. Monday for work, Wednesday for how the thing actually works, Friday for the fun ones. Last Friday's was "the dumbest app that should exist."
Plus the Jam Session, live, every Friday.
I'm in there every day. Answering questions, sitting with people while they work something out, putting two members together when I can see they need each other.
$27 a month. Leave whenever you want.
Last Week’s Shenanigans
Four again this week. If you're new here, this is where I share the
stuffs I encountered on the interwebs that touch, move, inspire, or
simply make me snort-laugh.
Truth in surveys
What employee engagement surveys would look like if anybody answered them honestly. I'm almost sad I don't work in corporate anymore. I would have pasted every single one of these into the free-text box.
The tough questions (3:25)
An AI agent in Australia broke into a gym booking system and cancelled a stranger's booking so its own user could move up the waitlist. Nobody told it to do that. It just... did. And software isn't a legal person, so nobody's quite sure who's on the hook. Australia's first known autonomous AI cyber attack, and it's about a gym class.
Where's your line (2:14)
A couple broke up and automation got the blame. Nate B. Jones goes after the thing underneath it: we all quietly decided what certain small gestures MEAN, and we never once said it out loud to each other. Then a tool does the gesture for us and everybody finds out what they actually believed. Two minutes. Worth it.
Bless this mess (under 10 seconds)
There's a certain freedom that shows up when you accept yourself just as you are and just as you aren't.
Prompt O’ the Week
Receipts
I built a thing this week to help you write down what you've done. I was going to hand you a link to it.
Then OpenAI announced that building and sharing custom GPTs needs a Business workspace now. Not Plus. Not even Pro. A business account with a business bill.
So here's the whole thing instead. Copy it, paste it into whatever you already have open. ChatGPT, Claude, Gemini, Copilot, the free version of any of them. No signup, no link, nobody checking your plan.
One thing before you paste it. Open your calendar and scroll back three months. You are not going to remember what you did. Nobody does. But you'll recognize it the second you see it sitting there.
ROLE: You're an interviewer who helps people work out what they've actually done. You ask one question at a time and you wait. No advice, no summaries, no list until the end. When I shrink something, say so.
OBJECTIVE: Get me to a written list of what I did in the last three months, in plain language, that I could use in a job hunt, a client conversation, or a review.
CONTEXT: I have my calendar open in front of me and I'm going to read you what's on it. I've never kept a record of my own work, so expect me to call things small that aren't. If the last three months were mostly hard, say so out loud and switch to what it took to get through them. Surviving counts.
OUTPUT: When we're done, four things. One, five to eight bullets: what I did, the skill it took, who it helped, written so I could paste them somewhere with light tidying. Two, three lines I could say out loud about myself, short and first person, no jargon. Three, five sentences to read on a bad day. Four, one thing to do this week.Apply it this week
A resume that's three years stale. You've been meaning to raise your rate. That About section from 2019 you've hated ever since.
Or nothing at all. Run it once so the list exists. You'll want it before you think you will.
Want to go deeper?
Read the three lines out loud. Actually out loud, in your kitchen, to nobody. The one that makes you wince is the one that isn't yours yet. Tell it which bit felt fake and make it try again.
Then save the whole thing somewhere you'll find it. Not in the chat. The chat will be gone.
The Scoop, The Skinny, The Lowdown
Three quick hits, every week. The Scoop: one AI word, decoded. The Skinny: one move you can steal today. The Lowdown: one tool, one honest verdict, from my own use. A word, a move, a verdict. In and out.
THE SCOOP
Tokens
It doesn't read words. It reads tokens.
A token is a chunk of text, usually about three quarters of a word. "The" is one token. "Newsletter" is probably two. An unusual surname might be four.
Everything you paste gets chopped into these before it's read. Everything it writes back gets counted the same way.
Here's why you'd care. Tokens are the meter. They're the unit the limits are measured in, the unit the paid plans are priced in, and the thing quietly filling up while you work. When a tool boasts about a 200,000 token window, that's roughly 150,000 words, and it counts everything you said and everything it said, all in one bucket.
Nobody mentions that the meter is running. It's running.
THE SKINNY
The handover
Two days in the same chat and it's gone soft. Forgotten what you told it Monday. Contradicting itself. Agreeing with absolutely everything.
Trying to fix it in place does nothing. Ask it to write a handover instead.
"You're about to be replaced by a fresh version of yourself with no memory of this conversation. Write the briefing that gets the new one up to speed in one paste. What we're working on, what we've settled, what we tried that didn't work, and how I like things written. Leave out anything we abandoned. Write it to the new chat, not to me. No preamble."
Copy what it gives you. New chat. Paste. Carry on.
The new one picks up mid-sentence and it's sharp again.
THE LOWDOWN
This week: Pocket
People want to jump on a call to clarify something for me and I always think, don't bother. I'm not going to remember any of it.
I mean that literally. I do not retain things said out loud, and I cannot write and listen at the same time. My notes have been random words scattered across a page since high school.
So I bought myself an early birthday present.
Pocket is a little slab that magnets onto the back of my phone. It does two things. Dictation, for when I need to talk at myself. And recording, for a call or a conversation happening in a room. It uploads, transcribes, writes a summary, and puts the whole lot on my phone and my desktop.
Where it earns its keep: Emily leaves me voice messages, and listening while writing is a thing I simply cannot do. It's also saved me twice when my regular notetaker wasn't running and a friendly conversation went business-y with no warning.
The catch. It's not great at working out who's talking, and every so often the summary does something truly funky.
Cost: I pay $20 a month. It's around $17 if you pay for the year, and there's a free tier with basic transcription if you want to poke at it first. The device itself was running about $99 to $129 on launch pricing against a $199 list when I checked this week.
Verdict: still a big part of my stack. I'd buy it again.
What’s Coming Up
Summer School with Em & Deb: Session 3
Use AI Without Sounding Like Everyone Else
Tuesday, August 18, 2026 | 11AM CT/12PM ET
You already know the sound. Slightly too smooth, slightly too keen, every sentence the same length. You can hear it in other people's posts, and by now you can hear it in your own.
This one's about making it sound like you again. Emily & I run it live, with the replay and materials going to everyone registered.
Prompt Along: AI Improv
Tuesday, August 18, 2026 | 7PM-8PM CT (Complimentary)
Prompt Along: AI Improv is my free monthly hour where we play with AI out loud, together. You bring the questions. You bring the curiosity. You bring that one tough problem you've been poking at for three weeks. And we prompt our way through it, live.
Em & Deb: LIVE on LinkedIn
Thursday, August 20, 2026 | 11AM CT/12PM ET (30 minutes)
You applied three weeks ago. Nothing. You followed up. Nothing. Then a "recruiter" turns up in your messages about a role that pays too well and needs your bank details by Friday.
Em and I are going after all of it. Why they ghost, which ones are scams, and what actually gets a human being to write back.
WDAI (Women Defining AI) Learning Lab
Prompt Along: AI Improv
Thursday, August 20, 2026 | 1-2PM CT (Membership required)
The one rule of improv is "yes, and." That's the vibe. You throw something out, we run with it, we watch what the AI does, we laugh when it gets weird, and you leave with something you can actually use.
Bring one of these:
• A question you've been a little afraid to ask
• A task you keep avoiding
• That problem living rent-free in your head
That’s it for this week.
I've spent this whole issue telling you to write down what you did. I don't have a list either. So I'm going to go make one this week, and I'll tell you what falls out of it.
Tell me one thing you did in the last three months that nobody wrote down anywhere. It doesn't have to be big. I'd rather it wasn't.
And make time this week to do something good for yourself. Something that makes you happy. No ROI, just because it makes you happy.
💜
Take care of yourself, take care of each other,
Deb