It's the Sunday of Memorial Day weekend and I have to say, it's the perfect time to hit the milestone of 50 newsletters in a row.

I mean, I'd like to say that I planned it but with pretty much everything else with the last 2+ years, I often take action before I actually plan anything. That's not entirely true - I have an overall goal in mind (freedom from corporate and location tyranny for my hubby and myself) but rarely know the steps to get from where I am to there. It's more like - let's try this! Did that work? No? Hmmm... what about... THIS?!

Things in life and in business are doing pretty good right now. I mean, I'm not selling a whole heckuvalot but I am starting to have people reach out to me for things I'm actually pretty good at and that I genuinely enjoy doing.

And of course, I get to spend plenty of time in various AI tools building stuffs and nonsense and talking to extraordinary humans so I got that going for me. Which is nice.

Don't quote me on this - and a part of me feels like I shouldn't even write this 'out loud' 'cause then I'd surely be tempting the gods, but I think this may actually be what momentum feels like. I can't be entirely sure because I've honestly never thought about it very much.

Alright, I feel like I should put some elevator music here or something because I just had to look up momentum and of course my head is spinning with physics explanations. Basically, it's mass in motion.

Which describes me pretty well if motion is posting things online, building stuff with AI tools, and talking to a lot of different people. I mean, most days I'm sitting on my ass for long periods of time, but the fact that I do it consistently and keep doing it has somehow given me momentum (I think).

What has helped is that I've started to stop doing some things that aren't serving me or the business (or my husband, for that matter). This has been one of the hardest things as an ADHD founder who has realized that the barrier between an idea and creating that in the world is astonishingly slim.

For a long time I just kept building stuff because I could. And sadly, that's not the best habit to indulge in when you're trying to build a business that solves other peoples' problems. I can't solve every person's problems, as much as I'd like to believe I can.

So cutting out the extra stuff, the things that were draining my focus, has been an ongoing battle. The only reason I'm here right now is because I have an amazing support system of humans who love and care about me, and paid coaches and training (also with humans who love and care about me and who do this for a living).

The best part is that the weekly Friday Jam Sessions are starting to be the cohort of humans (primarily women with a few enlightened men along for the ride) I have been envisioning for months.

I tell everyone that I am a community ho (got in trouble for saying that once while in corporate and tried to distance myself from it because my boss's boss found it tacky). I love and live for communities. I'm currently a member in over 40 communities (I know this because the Chief of Staff I made last week has all of them listed in my new Notion 'brain').

Joy Prompt Club is the culmination of decades of dreaming - creating a community where I can be who I am without worrying about whether that's good enough, or nice enough, or right enough for anyone else.

When I come down to it - this newsletter and everything I'm building is the culmination of years of community with other humans who touch, move, inspire, and engage me. Creating spaces for people to show up just as they are (and just as they aren't) is what I live for. And now I get to do that for a living. Pinch me!

Here's what I keep forgetting: for years I said "I'm not a worksheet person." Said it like a fun fact about myself, like being left-handed. Workbooks, worksheets, fill-in-the-blank anything - not my thing. I'm a builder. I make tools. I don't make... paper.

This week I made a worksheet. An actual one. The Invisible Labor Audit, three columns; fill it in by hand if you want to. The exact format I'd written off for years. And it might be the most useful thing I've made all year.

So here's the uncomfortable part. "Just how I am" was hiding something. Not a quirk. A skill I hadn't bothered to claim.

But I want to be honest with you, because "just how I am" is a sneaky little phrase and it cuts two ways. Sometimes it's covering an asset you buried. And sometimes it's just armor - "I'm not a tech person," "I'm too late for this," "I don't do new tools" - a tidy way to stay exactly where it feels safe.

The work is telling which is which.

So this week, pick one. One thing you've decided is "just how you are." Then ask the honest question: is this protecting something real about me, or is it a wall I built on a day I was tired?

Your years of doing things your way are not the problem. Some of them are the whole point - and you've been apologizing for them.

The stuff that touched, moved, and inspired me this week. Or in the case of the last one, made me laugh entirely too hard.

After Automation
Fair warning: this one is LONG. Pour the tea, settle in. But it's worth the time, and here's the real reason to click - the graphics are next-level. Scroll all the way to the bottom and move your mouse over the last one. I'll wait. The argument underneath all of it is the thing I keep circling back to lately: as AI gets better at doing, the rare and valuable thing becomes knowing what's worth doing. Hold that thought - it shows up again in this week's freebie.

I’m pretending and it’s all on you
A confession, and it is also a documentary about me. If you and I are ever in a situation that requires doing math in our heads, please know: I am not doing the math. I have never done the math. I am here for moral support while your brain handles the numbers. The second numbers enter a conversation, mine simply leaves the building. He says it better, and in under a minute and a half.

One minute of red pandas
Sixty uninterrupted seconds of red pandas, who turn out to be a cross between a bear, a dog, and a fox. I did not know this. I feel like I should have known this. I can tell you in excruciating detail how to survive quicksand - a threat I have encountered exactly zero times - but the red panda situation was apparently never covered. Anyway. Now you know too.

Pedro Pascal talks puppy
One of the most heartwarming things I saw all week, no notes. Filed under proof that a man can be deeply, ridiculously manly and also melt completely into a pile of puppies. The two were never in conflict. Some of us have been saying this for years.

A song you didn’t ask for
Fifteen seconds. That's the whole ask. I will be singing it for no fewer than seven more days and now, regrettably, so will you. You're welcome.

Turns out newsletters don't pay for themselves. Who knew?

A note from this week's sponsor. This one's not aimed at us - it's serious software for companies trying to figure out their AI exposure. I'm including it because the company looks sharp and the problem is real, and I'd rather show you the whole landscape than just my corner of it.

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It's a worksheet - my first real one, which Radical Remembering already confessed enough about. One page, three columns, about fifteen minutes.

Here's the whole idea. There's a pile of work you do that nobody counts. Not your job, not on any list - the remembering, the tracking, the drafting-in-your-head, the mental tabs that never close. The Audit is for naming that pile, then sorting it: what AI could actually take, what it can't, and the one thing you'll try this week instead of carrying it for another month.

Quick reminder for anyone new: ROCO is how I build a prompt without overthinking it. Four parts - Role, Objective, Context, Output. Who the AI should be, what you want, what it needs to know, and what the answer should look like.

This week's prompt pairs with the freebie. Once you've filled in your Audit and you've got that one row you want to hand off, this turns it into a real conversation instead of a guessing game.

Two things to notice. It's an interview - the AI asks, you answer, no big paragraph to write up front. And it runs a little inference audit at the end: before it does anything, it checks what it's still missing. Because the AI isn't in the room with you. It doesn't know your life. If something matters, it has to ask.

Copy this in:

If the AI starts guessing instead of asking, just say "ask me, don't assume." That's the whole skill.

The Matriarchy Minute is where I spotlight women doing work in AI that you should know about but probably don't.

This week: Vanessa "Ness" Monsequeira

I first met Ness in the Open Org community, right around the time of my own layoff. She was just stepping into her role as VP of People at Gorilla, and she shared the whole thing publicly - what starting the job actually felt like, what she wanted to build. I admired her from a distance and never quite stopped.

As a woman of color, she's had to clear hurdles that were never put in front of me. She's done it with passion, grace, and a kind of strength I don't think she'd even name in herself. Those are only a few of the reasons I admire her.

Here's the part worth your click. Ness now runs her own practice, intelligence rewired, helping companies adopt AI without losing trust or their best people. Her whole argument: AI projects fail because of people, not technology - companies hand staff the tools before anyone's learned how to think with them. Sound familiar? It's this week's newsletter in a different accent.

Find Vanessa on LinkedIn.

Friday, May 29 | 10:30 AM CDT (Time change - this is the last time for a while, I think)
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.

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.

Fifty weeks ago this was an idea I had no plan for. It's still mostly that. Thank you for being here - first issue or since the wobbly early ones. Here's to the next fifty.

💜

Take care of yourself, take care of each other,

Deb

P.S. Go fill in the Invisible Labor Audit. Not someday - this week. Pick one row, try one thing, and have something off your plate in about fifteen minutes. Here it is.

P.P.S. I love hearing from you. If you've got an AI problem you're chewing on or you just need a human to talk it through with, hit reply. That inbox is me. It's always been me.