Hey beautiful human,
I am in complete denial that we are nearing the end of July of twenty twenty six.
More than halfway through the year and I'm sitting here wondering what the hell happened to the whole first half. I had so many big plans. So many things that were gonna get done and get clarified and get cleared up, so many clients I was going to sign, so much income I was gonna make. Granted, a lot of it's come true. And a lot of it is still as much of a clusterf*** as it was at the beginning of the year.
Let me tell you about Monday.
I dragged butt from the moment I woke up. Sleepwalked through most of the day. Then I had a big planning meeting with Emily Worden in the afternoon, and by the time I was done with that, Smidge had come home. He'd been on call the week before, so that week and weekend had already been stressful before Monday even started.
So I took an unplanned nap. Woke up around a quarter to nine and realized I had a lot of stuff I needed to process from the meeting with Emily. I sat down at my computer and I was just gonna do one or two things.
Before I knew it, it was two AM.

My project management system at 2:30 AM. Fully coherent. Ask anybody.
My head was swimming with all of the different moving parts that are required when you're setting up an event like this. A multisession event. Marketing. How to communicate it, how to advertise it. Not to mention actually creating the course material itself and then designing the products that go along with it. This is my first time coordinating something of this extent on my own, and I was very overwhelmed. At around two thirty, three in the morning, I was tossing everything into Fable (Claude’s super-powerful-super-expensive-most-capable model) to help me untangle where my brain had taken everything. A couple more hours and I had it figured out into a master plan and knew exactly what to do next.
By that time it was already Tuesday, and I couldn't really bail on the rest of the day.
So I started the week with a deficit, and it just kept compounding as the week went on. Even when I would stop to take a rest, it was literally just catching up with where I had robbed myself earlier. I wasn't restoring anything. I was constantly borrowing.
Which, now that I look at it, is pretty much how I've lived most of my life. Always borrowing from something in the future, whether it be time or money or worry or any of those things. Very rarely just being in the now.
It really is an account that you have with yourself and your body when you rob yourself of the rest that you need.
And here's the part I didn't know going in. There's a difference between working ON your business and working IN your business. ON is all the back office administrative stuff that just keeps things running, including your business development. IN is the actual doing the work for your clients. That two AM night was all ON. Nothing I could show anybody. No invoice, no client, no deliverable. Just moving parts getting arranged.
That's where the first half of my year went.
If I would have known that ahead of time, it might have stopped me from actually pursuing a business.
I say might because the plain truth is that I feel more alive now, even with the double duty of entrepreneurship, than I have any other time in my adult life.
My buddy Nicole wrote an article about the difference between rest and restoration, and it's absolutely brilliant. I think it's the secret to why so many of us are constantly hovering on the borderline between being okay and being burned out. Or maybe it's between bored and burned out, because there's a boundary line there we're constantly balancing on.
Summer School with Emily kicks off Tuesday. I'm excited and scared and thrilled and freaking out.
So. What's your account look like right now, and what did you spend it on?
Radical remembering
Here's what I keep forgetting: the nap doesn't count.
You sleep in on Saturday and call it rest. What you actually did was make a payment on the four hours you took out of Tuesday. The balance goes down a little. Nothing got deposited.
Which is why you can take the whole weekend off and show up Monday still running on fumes. You weren't resting. You were servicing a debt.
And once you catch it in sleep, you start catching it everywhere else. The money you'll make later. The worry you're doing right now on behalf of a Thursday that hasn't even happened yet.
Nobody sends you a statement. That's the trouble. Your body just quietly keeps extending you credit, and you keep taking it, because it's the one lender that never calls.
Restoration is the thing that puts something back in. Which means it can't be the eight hours you were already going to sleep anyway.
You already know what yours is.
Go put something in this week.
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.
Why AI makes the humanities more important than ever
Nearly 15 minutes long, so save it for when you've got the time. But it's something a lot of you need to hear, especially those of you who think you're not technical enough or "smart" enough for AI. It's an engineer from IBM, talking in plain language about why your experience is exactly what's needed here.
Tough enough?
I've been a fan of Slim Sherri for quite some time because her brand of GenX humor and snark feels like a warm hug of familiarity. Here she takes on the younger folx who don't think she's tough enough to be on social media.
Firestarter rebooted
Huge thanks to my buddy Marion for turning me on to this account. This is the kind of senseless whimsy I live for. Reminds me of working in the cafeteria at St. Olaf College.
Tata otter
Ten seconds of kewtness that triggers my cute-aggressive impulse to an alarming degree. But not so alarming that I won't share it with all of you.
This week’s freebie
Make It Interview You
The hardest part is usually the blank box. You don't know what to type, so you type nothing. Here's the move that breaks that every time: make it ask you.
When I'm stuck, I don't write a perfect prompt. I say: "Before you write anything, ask me one question at a time until you know enough to do this well. Then do it." And it starts interviewing me. My answers turn into the prompt I couldn't write.
You don't have to show up with the right words. You just have to answer questions, which you already know how to do. It pulls the project out of you instead of waiting for you to hand it over perfectly.
Now you. Pick something you've been circling. A message you can't start. A decision you keep avoiding. A plan stuck in your head.
Type this: "Ask me one question at a time until you understand what I need. Then help." Answer honestly, like you would a nosy friend. Let it dig.
Too many questions, or dumb ones? Steer it. "Fewer, sharper questions." Or just call it: "Okay, that's enough. Go." You're still the boss here, same as Lesson 1. The interview is just a faster way to tell it what you mean.

Make It Interview You
This is Lesson 7 of You're the Boss of This Thing, my new little course living inside Joy Prompt Club. Seven lessons, real moves; you set the pace. Come boss some bots around with us.
ROCO Prompt O’ the Week
The 2AM Tangle.
Monday night I sat down to do one or two things and looked up at two in the morning with a head full of moving parts. Sessions, marketing, course material, what to send and when. All of it real, all of it at once, none of it in any kind of order.
So I dumped the whole mess into an AI and let it ask me questions until the pile turned into a sequence. Under twenty minutes and I knew exactly what to do next.
This is that. Bring it messy...
**Role:** Act as a calm project strategist who has untangled a hundred of these. I'm not organized right now and I'm not going to pretend to be. Your job is to pull the pile out of my head, one question at a time, and hand it back to me in an order I can actually work. You are doing the sorting, not assigning me the sorting.
**Objective:** Turn the tangle in my head into a sequenced plan with a clear first step I can do before I go to bed tomorrow. Good means I close this knowing exactly what to touch first and what I'm allowed to ignore for now. Bad means I get a tidy list of everything I already knew, which is what I have now.
**Context:** Interview me one question at a time. Wait for each answer before asking the next. Ask, in this order:
1. What's the thing? Describe it however it comes out. Messy is fine.
2. Dump everything you can think of that's part of it. No order, no filtering. Just empty your head.
3. Now look at what I gave you and tell me what's usually part of a thing like this that I did not mention. Name the specific missing pieces and ask me whether each one is in play. Do not ask me a general question like "anything else?" - I've been staring at this too long to see the gaps.
4. Who else is in this? Anyone who has to approve something, reply to something, send me something, or say yes before I can move.
5. What has a real date attached to it - something outside me that won't move?
6. What are you dreading most in that pile?
7. How many hours a week do I actually have for this? Real hours, not the hours I wish I had.
If I answer #7 with a number that sounds aspirational, ask again and ask what else is in my week.
If I say "I don't know" to anything, ask a smaller version of the same question.
When you're done, do not read my answers back to me.
**Output:**
- **The order.** Everything I dumped, sequenced by what has to happen before what. Not by importance. By dependency.
- **Waiting on people.** Every item that depends on someone else, and how early I need to ask them so they don't become the reason this stalls.
- **Not yet.** What I can safely ignore right now, and the moment each one wakes back up.
- **The dreaded thing.** Where it actually belongs in the sequence, and whether it's as big as I think it is.
- **What you think is really going on.** Based on what I told you, name the thing I'm actually stuck on. Say it plainly even if I didn't ask.
- **First step.** One thing, small enough to do before I go to bed tomorrow. Name it specifically.
If anything here needs a decision only I can make, list those separately as open questions. Do not guess at them.What happens next
Seven questions, under twenty minutes, and your pile comes back in an order with a first step you can knock out tomorrow. Fair warning on the second-to-last one... it's going to tell you what you're actually stuck on, and it's usually right.
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
Reasoning models
You ask a question and instead of answering, it just sits there saying "thinking..." for twenty seconds.
Picture asking a group of friends where to eat. One of them says "Applebee's" before you've finished the sentence. The other goes quiet for a beat, runs through who's vegetarian, who hates driving, and what's even open on a Sunday, then names a place that actually works.
The pause was the good part. That's a reasoning model. It works the problem privately first, catches its own mistakes, and only then talks to you.
Worth the wait when the question has moving parts. Not worth it when you just want a shorter subject line.
Most tools let you flip it on and off. Now you know what that button's for.
The Skinny
Tell it what never to do.
We all describe what we want and then quietly hate what comes back. The missing half is the other list.
"Never use the word 'delve.' Never open with 'in today's world.' Never end by summarizing what you just told me."
I keep a running list of the things that make me stop reading mid-sentence, and I paste it into anything serious. It gets longer every time something annoys me. It is far and away the fastest way to make AI output stop smelling like AI.
Start yours with three. You already know what they are. They're the phrases that make you close the tab.
The Lowdown
This week: Perplexity
Ask a regular AI about something current and it'll answer with total confidence from whatever it happened to absorb in training. Ask Perplexity and it goes and looks first, then shows you the links it used. Little numbered citations, right there, clickable.
This is my research tool. Anything where I need current data - pricing, who's doing what now, what changed last month - I go here first and nowhere else comes close. If "but how do I know it isn't just making things up" is the thing keeping you at arm's length from AI, start here. You can check its work.
It's also weirdly great at errands. Tell it every stop you need to make and it hands you back the order that makes sense.
Which is why the other day stung a little. It gave me directions to a place and put it in the wrong spot. The place was around the corner from where it sent me. Confident, cited, wrong.
So: a citation means it found something. It doesn't mean it read it right. Click through on anything that matters.
Also, don't ask it to write for you. It's a research tool wearing a chat interface. Ask it to draft something in your voice and you'll get beige.
Cost: the free tier is genuinely usable - unlimited basic searches, plus about five of the deeper "Pro" searches a day. Pro is $20 USD a month, or $200 for the year if you'd rather pay once and forget it. Students get it for ten. Their Comet browser is free for everyone now. Prices move, so peek at the live page.
Verdict: best research tool I've got. Just don't let it drive.
What’s coming up
Summer School Orientation

Summer School with Em & Deb: Free Orientation
Tuesday, July 28 | 11:00 AM CDT (1 hr, free)
The job search right now is a lot. You're not behind - you're flying blind. So Emily Worden and I built you an instrument panel.
Come to a free 1 hour Orientation and find the one part of your search that's costing you the most right now. You'll walk out knowing exactly where to start. Not twelve things. One.
No polished webinar. No 53-slide deck. Just a clear little block of time that makes the whole thing feel less impossible. (And yes, free prompts.)
It's the front door to Summer School, our workshop series for job seekers gearing up for the September Surge.
Em & Deb: Shoot the Sh!t (LIVE on LinkedIn)
Thursday, July 30 | 11:00-11:30 AM CDT
You hit submit. Then... nothing. No reply. No rejection. Not even a robot saying "thanks, we'll be in touch" (they won't).
So this week Emily Worden and I are going live for 30 minutes on the question every job seeker is muttering at their screen: is anyone actually seeing your application? Or is it face-down in a black hole with 200 other resumes?
Same deal as always. Bring your questions and your "is it me, or is it the machine?"
Prompt Along: AI Improv
Tuesday, August 18 | 7-8 PM CDT
Prompt Along: AI Improv is my new free monthly session. One hour. No script. You bring the questions and the curiosity (and that problem you've been avoiding), and we prompt through it live, together.
Think improv, not lecture. "Yes, and" energy. The room runs the show.
First one is Tuesday, August 18, 7:00–8:00 PM CDT. It's free. Come play. And bring your friends; the more the merrier!
That's it for this week.
Here's the part where I'd normally tell you what I'm doing differently.
Summer School starts Tuesday. I'm going to be up too late at least once. We both know it. I'm not standing here promising you a bedtime I have no intention of keeping.
What I will do is put one thing in the account this week. One deposit. Small counts.
Your turn. Find the thing you've been calling rest that isn't, and give twenty minutes to something that actually puts something back. Sit outside and do nothing on purpose. Call the friend who makes you laugh in that undignified way where you can't get the words out. You already know what yours is... you've been putting it off for a while now.
Then hit reply and tell me what you picked. That inbox is me. Always has been.
💜
Take care of yourself, take care of each other,
Deb
P.S. If you run the Untangle prompt and it tells you something uncomfortably accurate about what you're actually stuck on, I want to hear about it. You don't have to write me an essay. "Yep, it got me" will do fine.

