I have two weeks of unemployment left.

$759 a week. Then it stops.

My debt is over $2000 a month - and that's not including mortgage, food, utilities, or the truly alarming amount I spend on cat food. I've been job searching for seven months. Applying to jobs I don't even want because the algorithm has decided I'm overqualified and somehow not quite right at the same time.

Meanwhile, I've been running free AI sessions. Building resources. Teaching midlife women that they haven't missed the boat with AI. And people keep showing up. They leave feeling capable instead of behind. They send me messages saying it helped.

But I haven't been asking them to pay.

This week I did something I've been avoiding: I asked ChatGPT for radical candor. I told it I needed concrete actions to get money into my bank account. I told it about the two weeks and the debt and the crickets from job applications and the panic.

And ChatGPT - bless its algorithmic heart - told me what I already knew but wasn't ready to hear: "You have a market-ready offer that just needs distribution."

Which is consultant-speak for: Deb, you have something people need. Stop giving it away and ask them to pay for it.

So I did what any reasonable person does when confronted with uncomfortable truth: I went looking at my data. I have 35 survey responses from people who've attended my live AI Confidential sessions. Plus all the feedback Emily Worden collected from our October 2nd workshop.

I'd looked at it before. But I hadn't really seen it.

Because here's the thing about ADHD: even effusive praise lands like "well, they didn't hate it." Someone writes "This was amazing, funny, real vibes with AI!" and my brain files it under "okay, so it wasn't a disaster."

But when ChatGPT told me I had something market-ready, I went back and actually read what people said:

"Deb's positive energy and amazing vibe kept my attention throughout the event."

"Loved the perspective of looking at AI as a language tool versus a technology tool."

"Deb was amazing — quirky and effective. Her sessions are to the point and no fluff."

"Your personality is fun and put everyone at ease — made everyone comfortable participating!"

Not "it was fine." Not "didn't hate it."

People paid attention. They participated. They left feeling capable.

That's not charity work. That's a service people need.

So I'm learning how to ask. Not because I suddenly figured out how to be confident about selling. Because two weeks is a deadline that doesn't negotiate, and apparently I've been sitting on proof this whole time.

While I was having my "oh, people actually value this" revelation, here's what else caught my attention…

You Taught Me Something Today

Braxton Baxter went back home to his small town and had a conversation with one of his parents' friends. I was crying by the end. Sometimes the risks of going home pay off in beautiful ways - and sometimes strangers teach you exactly what you needed to hear.

Wait, you did WHAT?

Little known fact about me: I once did English dub acting (voice acting for anime). Yes, I was the Evil Hospital Director in Episode 3 of Nerima Daikon Brothers. And yes, I am actually listed in IMDB. Here's proof I contain multitudes. (Heads up - that ‘proof’ link is a very dated YouTube of my performance… it’s a bit lengthy)

Days That Matter in November

daniela (dani) herrera is legendary when it comes to DEI work, and she posted all the important days in November worth recognizing: November 16 is International Day For Tolerance, November 20 is Transgender Day of Remembrance, and November 25 is the International Day for the Elimination of Violence Against Women. Because knowing what to honor matters.

Partner of the week

Turns out newsletters don't pay for themselves. Who knew? This week's partner helps keep the lights on – and their work is legitimately useful (I subscribe to this newsletter myself!):

AI will eliminate 300 million jobs in the next 5 years.

Yours doesn't have to be one of them.

Here's how to future-proof your career:

Start learning AI now

AI-Powered Gift Giving for Humans Who Are Tired and Broke

7 conversational prompts to help you give meaningfully - without guilt, stress, or maxing your credit card.

Let’s be honest: gift-giving has gotten out of hand.

You’re trying to be thoughtful and responsible while capitalism whispers “but have you tried MORE STUFF?”

This week’s freebie helps you outsmart the chaos with 7 conversational AI prompts that make generosity feel human again - even when your wallet’s on strike.

Here’s the wild thing about asking: most of us can do it for others, but freeze when it’s for ourselves.

That’s where ROCO comes in.

Role
You are my calm, confident coach who helps me ask for what I need without apologizing for it.

Objective
Help me draft a short, clear request that feels honest but not desperate.

Context
I need to ask for [something — money, help, visibility, opportunity] and I’m overthinking every word. Remind me that I’m allowed to ask, and help me find language that fits my real tone and situation.

Output
Write one version that’s warm and human, and another that’s more direct and concise.

Why this works: AI doesn’t have your shame reflex. It can help you practice asking - not perfectly, just out loud. When you see the words, you start believing the ask is possible. And that’s the moment things start moving.

💡 Remember: If the first version doesn’t sound like you, say so.

Tell ChatGPT what’s off - “too formal,” “too soft,” “too salesy” - and ask it to adjust. AI doesn’t get offended. You’re the director. It’s your voice. You get to guide it.

✨ Try it in ChatGPT (free version works great):

(Paid Session - $20 · Includes Replay + 25-Prompt Pack + ROCO PDF)

🗓 Tuesday, November 18 · 12 PM CST / 10 AM PT / 1 PM ET

Feeling behind on AI? You’re not - you’re just overloaded.

In this 60-minute live session, we’ll turn “too much” into “I’ve got this.”

No jargon. No overwhelm. Just calm, practical confidence - and prompts you can actually use the same day.

Includes replay access + 25-Prompt Pack + ROCO Quick-Reference PDF.

💜 Know someone drowning in tech overwhelm?

Send them this link. It’s a $20 transformation from panic to confidence - and yes, they’ll thank you later.

(Free Session – same day and not recorded)

🗓 Tuesday, November 18 · 8 AM – 9 AM CST / 2 PM – 3 PM UK

Want to dip your toes in first? Come to the free, judgment-free intro session that morning - playful, private, and grounded in psychological safety.

No recording. No pressure. No performance.

Just a safe space to explore. Come as you are - this is AI, but make it human.

That's it for this week.

I’m still learning how to ask. Still trying to believe that what I’ve built is worth paying for. Still occasionally using Perplexity to confirm whether it’s possible to live on caffeine and vibes alone.

But I’m also learning that asking isn’t weakness - it’s data.

And apparently, the data says: people do want what I’m creating.

So if you’re in your own version of the messy middle - the “holy hell, I think I’m onto something but I’m also broke and exhausted” phase - consider this your reminder: you’re not behind. You’re just building without a map.

💜

Take care of yourself. Take care of each other.

And if all else fails, remember: the rails were always optional.

Deb

P.S. Forward this to someone who’s out there quietly doing brave, unglamorous work. They probably need the reminder that messy doesn’t mean wrong.

P.P.S. I’ll be over here feeding the cats, refreshing Gumroad, and practicing my own advice about asking. We’re all just figuring it out - one mildly panicked prompt at a time.