Hey beautiful human,
I'm writing this from a hotel in Denver, Colorado. My hubby is watching football (it IS Sunday during football season, after all) and I'm perched on the bed with my lappy on one of those nifty laptop desks.
My knees are complaining a bit after 15 hours in a car over the last two days, but that's a small price to pay for being on a new adventure in a city I've spent very little time in.
Tomorrow is FPPIRL - Fractional People People in Real Life.
There's coworking during the day, then a happy hour at 5PM to officially kick things off. Tuesday and Wednesday are two full days of hanging out with other fractionals, working on our businesses and connecting with each other.
This is my second time attending and I'm stupid excited.
I get to reconnect with folx I've already met AND finally meet people I've only known as tiny rectangles on Zoom or names in Slack.
If you don't know what a fractional is, don't worry. Basically, experienced people in HR, Marketing, Finance, Operations, Tech, Legal, etc. work inside one or more companies without becoming full-time employees of those companies.
Which means you're doing the work you've done for years...
while also running a business.
And THAT part is where things get interesting.
You have to find clients. Sell your work. Figure out pricing. Do marketing. Keep the pipeline moving. Deliver what you've already sold. Occasionally remember that taxes exist.
It's why the whole "feast or famine" thing happens. Client work gets busy, your own business gets ignored, then one day you look up and realize the work ends next month and you haven't told another human you exist since February.
FPP is mostly CHRO / executive-level HR and People folx doing some version of this strange little dance. I've been part of the community for two years now and it's easily one of my top three.
And this is coming from a self-proclaimed Community Ho who belongs to nearly 40 communities at last count.
After FPPIRL, Smidge and I are staying in Denver a couple extra days so I can hang with my bestie Nicole Eisdorfer.
Naturally, I'll also be working.
Because apparently "traveling while self-employed" means taking your laptop somewhere prettier.
Emily Worden and I are doing another LinkedIn Live to launch Fall Lab, the next thing we're building after Summer School.
And this time I am automating as much of the behind-the-scenes stuff as humanly possible.
Summer School worked. People bought it. People showed up. People got things from it.
Behind the curtain?
There was a LOT of Deb staring at spreadsheets trying to make sure the right person got the right thing and the wrong person did not get another email after asking to be removed.
Claude did an heroic amount of spreadsheet eyeballing for me, because I would've gone absolutely batty doing it manually.
But I still had to coordinate the whole circus.
So Fall Lab is getting machinery.
Which feels appropriate because last week was basically one long experiment in Deb + machines + humans + occasional mild panic.
I had another committee meeting for my part-time gig and this time I had to lead it. 😳
I had my first experience with a chatbot doing something I absolutely DID NOT want it to do because I hadn't been clear enough in my instructions.
It sent an email.
An email I had not approved.
😳
Lesson learned rather aggressively.
I ran another Prompt Along: AI Improv session with about 15 attendees, where people throw ideas at me and I build with AI on screen. I'm still figuring out exactly what this thing wants to become, but I think at least a couple folx had fun.
And then Thursday I did my assessment to become a Certified OpenAI Academy Facilitator.
Eighteen minutes.
Demoing how ChatGPT can review a Google Sheet, emails and a calendar, coordinate across all of them, and turn the workflow into a reusable Skill.
Three people watching.
One of them from OpenAI.
😳💦
Friday, though...
Friday was one of those days.
It did NOT begin auspiciously.
I pulled another hyperfocus night and finally went to bed around 5AM. Slept a couple hours, then jumped onto my Joy Prompt Club Friday Jam with a group of women who are so authentically cool that the fact they keep showing up every week remains one of the strangest and loveliest gifts this business has given me.
After that, I had two appointments scheduled at the same time. Because apparently Past Deb has opinions about Future Deb's capacity.
I popped into my Champagne or Espresso Book Club for about 15 minutes. That group has been going for NINE YEARS and we'd just come back after our two-month summer break.
Then I jumped into an AI for HR Founding Advisors meeting.
Then I joined the next meeting while getting into an Uber to go pick up the rental car that Smidge and I would drive from Minneapolis to Denver.
And y'all...
I LOVE road trips.
Like, ADORE them.
Especially with my hubby.
There's something about being on the road, suspended between here and there, that makes my brain ridiculously happy.
So after I picked up the rental car and drove over to Great Clips for a buzz cut, I was sitting in the parking lot reading messages from some of the fabulous women I'm building things with.
Nicole is one of them.
And I started crying.
Apparently gratitude exits through the eyeballs.
Not sad crying.
The kind where your chest gets too full and your body apparently decides the excess has to leave through your eyeballs.
I was just so completely overwhelmed by how f***ing lucky I am to be living this life with these people.
None of this would have happened if I were still a full-time Manager at Accenture.
I wouldn't be sitting in a rental car with a freshly buzzed head, reading messages from women I'm building businesses with, about to drive across the country with my husband to spend a week with people I chose.
My life is unrecognizable from two years ago.
Some days I'm scared sh*tless.
Most days?
I'm excited. Challenged. Ridiculously fulfilled.
And apparently crying in parking lots.
Weekly Ad
This week’s ad partner is Skydive. This is a new tool; just released in August 2026. Most of the feedback I read has been positive and I gave it a spin myself and was pleasantly surprised. The only thing I’m skeptical about… You have unlimited agents on the $20/month plan BUT you may get charged for the AI model you use to process the request. I’ll keep you updated as I use it more.
What’s still sitting on your to-do list?
You don’t need an AI team to build an AI agent. With Skydive, the person who knows the work can create the agent to do it.
Start an agent off with a role, teach them how your team operates, connect your tools, and put them to work.
Radical Remembering
Here's what I keep forgetting: fear is a witness, not the judge.
Somewhere along the way, fear got promoted. Now it rules on everything.
Scared means stop. And anyone who picks the uncertain path while the safe one is sitting right there is being irresponsible.
Especially for women. We're supposed to have a backup plan and sensible shoes, plus a ready answer for anyone who asks, "But what if it doesn't work?"
Fear gets to testify.
It can tell you the money feels uncertain and the plan isn't finished.
Fine.
It doesn't get the gavel.
You do.
Last Week’s Shenanigans
Three 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.
The Compliment (32 seconds)
Getting diagnosed with ADHD was HUGE for me. It explained so many things about my past and gave me a much better understanding of how to work WITH my brain going forward. This little 32-second video does a great job of showing something that may be invisible to someone with a neurotypical brain.
The Real Realtor (1:31)
First time I've come across this creator and I have to say... props for a very original take on showing a home. A friend of mine who's vocally anti-AI sent it to me and I'm not entirely sure it had the effect he was hoping for. Anyway, it gave me a giggle and I will always appreciate truth-telling in its many forms.
Truthy email sign-offs
You don't need the sound on to fully appreciate this one... although if 70s disco is your jam, SOUND UP. I would personally like several of these approved for immediate use in business correspondence.
Prompt O’ the Week
The Fear Audit
I can talk myself out of damn near anything if I'm scared enough.
They'll think I'm ridiculous. I'll lose money. I'll regret it. I'm not ready. Better wait.
Give me ten minutes and I can turn a feeling into a full PowerPoint deck, complete with supporting evidence I mostly made up myself.
Which is a problem when the thing I'm afraid of sounds exactly like something I know.
So this week, we're making AI do the sorting.
Paste in the prompt below. It'll interview you one question at a time, then separate what you actually know from what your brain has quietly filed under FACT.
ROLE:
Act as a clear-eyed thinking partner. Help me separate facts, fears, assumptions, and things I simply don't know yet.
OBJECTIVE:
Help me look at a decision or situation I'm worried about without talking me into or out of anything.
By the end, I should be able to see which worries are based on evidence, which are predictions or assumptions, and what I still need to find out.
CONTEXT:
Interview me one question at a time.
Start by helping me name the decision, situation, or possibility I'm worried about.
Then keep interviewing me based on what I actually say.
Your job is to understand:
what I'm considering
what I'm afraid might happen
what has actually happened already
what I'm assuming or predicting
what information I'm missing
what small thing I could test before making a bigger move
Do not decide all of your questions in advance.
Do not ask multiple questions at once.
Wait for my answer before choosing the next question.
If I say "I don't know," ask a smaller, easier question that helps me get closer.
Do not reassure me. Do not give me a pep talk. Do not make the decision for me.
If the fear involves immediate safety, self-harm, abuse, a medical emergency, legal jeopardy, or a major financial decision with serious consequences, stop the exercise. Tell me clearly that this is bigger than a reflection prompt and encourage me to contact an appropriate qualified person or emergency resource.
Keep interviewing me until you have enough information to sort what I've told you clearly. Then go straight to the four sections.
OUTPUT:
Create four sections:
What I know - facts supported by what I told you
What I'm predicting - things I may be treating as facts that haven't actually happened
What I don't know yet - missing information that could change the picture
What I can test - one small, reversible action that would give me more real information before I make a bigger decision
End with one sentence naming the fear that appears to be carrying the most weight.
Do not tell me whether that fear is reasonable or unreasonable.
Start with your first question now.Apply it this week
Use it on something real.
Taking the client. Leaving the job. Raising the price. Going to the event alone. Starting the thing before you know whether it'll work.
You're not asking AI for courage.
You're asking it to help you see what fear has been presenting as evidence.
Want to go deeper?
After you get the response, ask:
"Which item in 'What I'm predicting' seems to be carrying the most certainty in the way I described it? Show me what I said that made you put it there."
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
Tools
Say you ask ChatGPT, “Find two open 30-minute spots on my calendar tomorrow afternoon.”
If ChatGPT can actually look at your connected calendar and check what’s free, it’s using a tool.
Same thing if it reads a Google Sheet, searches the web, checks your email, or creates a draft in another app.
Different AI companies use slightly different technical language for this, but “tools” is the plain-English umbrella I’d use here.
Weekend language: the chatbot isn’t only answering from the chat anymore. It can reach into something else you’ve connected and use it to help with the task.
THE SKINNY
Name the permission line
If AI is doing anything that could actually do something - send an email, change a record, create an event - tell it exactly where it has to stop and ask you first.
Try: "Draft it, but do not send it without my approval."
I learned this one the fun way last week. (It was not fun.)
THE LOWDOWN
This week: Workona
Workona is a tab manager that lets me create separate Spaces for each project. Joy Prompt Club gets a Space. Emily gets a Space. OpenAI Certification gets a Space. All the tabs for that project live there, and when I switch Spaces, Workona swaps the tabs with me.
There’s a free plan with limits, plus a paid Pro plan if you need unlimited Spaces.
My verdict: I have approximately eleventy-billion things going on at once. Workona is one of the reasons Chrome has not become an archaeological dig.
What’s Coming Up
Em & Deb Shoot the Sh!t (LIVE on LinkedIn)
Thursday, October 1 | 11AM CT/12PM ET
Free. No slides. Bring coffee and the job alert that keeps sending you roles you’d never apply for.
Emily and Deb are talking about why finding jobs worth applying to can take all damn morning. We’ll take your questions, look at a few real search headaches, and give you a better place to start than scrolling LinkedIn until your eyes glaze over.
We’re also opening Fall Lab enrollment and telling you what we built to help you get this part of your job search done.
Watch, lurk, or complain about your alerts in the chat.
That’s it for this week.
By the time you read this I'll be somewhere in Denver with a bunch of HR/People folx, probably talking too much, laughing too loudly, and making at least one new friend whose name I will immediately forget.
(It's a gift.)
Before I go... I made you a thing.
A while back I built a Hype Card Generator because I think we are generally TERRIBLE at giving ourselves credit for the stuff we do.
Big stuff. Tiny stuff. Weird stuff.
Made the phone call you've been avoiding? CARD.
Finally figured out what that stupid setting does? CARD.
Got through a crap week without telling anyone to f*** all the way off?
Honestly, possibly two cards.
Mine this week?
I looked around at this weird little life I've built and realized I really, really like it.
Your turn.
What are you giving yourself credit for this week? Hit reply and tell me. I wanna know.
💜
Take care of yourself, take care of each other,
Deb