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Hey, beautiful human -

I’ve always been a weirdo.

Never quite fit. Learned to fake it (24 years in corporate will train you to perform “normal” so convincingly you almost forget you’re doing it.)

So when I started building this post-layoff life - this AI teaching thing, this newsletter, this weird rebirth - I spent six months “experimenting.”
Which, if we’re honest, was just fear wearing a lab coat.

Fear that if I showed up as myself, someone would quietly confirm the thing I’d suspected for years: that I wasn’t enough.
Not polished enough.
Not serious enough.
Just… too much and not enough at the same time.

And then reality tapped me on the shoulder. Twice.

First: At the FPP meetup in Chicago, my friend Rita looked at me - really looked - and said:
“You need to be a CHAD about pricing and selling.”

Let me pause and show you the exact energy she meant:

That unbothered confidence.
That “I decided I matter today” posture.
That wildly unserious swagger that somehow convinces the world to believe it too.

I laughed. I wrote it down. I absolutely did not embody it.
But something about that moment stayed with me.

Second: October 31 arrived. Seven months unemployed - the longest stretch of my entire adult life. No interviews. No leads. Nothing on the calendar except my own thoughts and a whole lot of silence.

In that quiet, I had to admit the truth:

I’d been hiding behind “experimenting” because it was safer than wanting something that belonged only to me.
Safer than trying.
Safer than caring.

So I finally did one small, brave thing.

Not a launch.
Not a brand.
Not a reinvention moment.

Just… I let myself show up as who I actually am.

Weird.
Funny.
Direct.
Human.
Me.

And you know what people told me afterward?

“Your energy is amazing, Deb! Truly this was the most fun session/webinar I've been on in literally ages.”
“I can't believe the time flew by so fast.”
“I will certainly recommend this to my girlfriends & female coworkers!”

For someone who spent decades sanding down her edges just to be tolerated in conference rooms, those words were a reminder of something I didn’t realize I’d forgotten:

People don’t want your palatable version.
They want the real one.

Which brings me to you.

You have pieces of yourself you’ve downplayed for years - instincts, quirks, abilities, curiosities - because someone once hinted they weren’t “useful” or “serious” or “grown-up.”

But those are the parts that make you unmistakably you.
Those are the parts that are trying to come back online.

I’m not asking you to build a business.
Or announce anything.
Or turn it into a project.

I’m asking you to remember something you misplaced while you were becoming “acceptable.”

There is a wild, bright, stubbornly alive part of you that has been waiting to return.

Let’s go find her.

Radical remembering

There's a part of you that went quiet when adulthood got loud.

Maybe she dimmed herself to fit into rooms that didn't deserve her. Maybe she learned to stay small because her joy made someone else uncomfortable.

She's still here.

This week, notice one thing you do instinctively - that you've been brushing off as "nothing."

A pattern you see before anyone else. A question that shifts the whole room. A curiosity you've been ignoring.

Don't evaluate it. Don't justify it. Don't turn it into a project.

Just notice it.

That's Radical Remembering.

Not reinvention - return.

A quiet reunion with the parts of you that were never the problem.

Last week’s shenanigans

Is Leadership a Public Health Issue?
Simon Sinek shared a short clip arguing that most of our stress comes from work - so leadership isn’t just a business problem, it’s a health problem. And next week’s A Bit of Optimism digs deeper with CEO Bob Chapman, who’s built a thriving global company on the radical idea that people come first.

The AI Learning Spiral (And How to Stop It)
Think With V - one of my absolute favorite creators - breaks down something I know intimately: how learning a new AI tool can start with curiosity… and then slowly tip into “I’m behind,” “I’m not enough,” and “I must catch up.” Her reminder? Use analog to process what you’re learning. Step away from the screen. Let your brain integrate instead of chase. I’ve found the exact same thing: you don’t learn AI by sprinting - you learn it by metabolizing.

Gen X Too Soft? Absolutely Not.
The Real Slim Sherri (a.k.a. the patron saint of generational chaos) responds to comments saying Gen X is “too soft” for social media - which is hilarious, considering we grew up launching our friends off seesaws for entertainment. This clip is pure nostalgia, pure feral energy, and pure GenX vindication.

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:

Stock Up Before It’s Gone: Sun Goddess Matcha Sale!

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This week’s freebie

The Stealth Skills Audit: What You're Accidentally Excellent At

You know what's wild? You're doing things every week that other people would love to learn. You just think it's "being helpful" or "how my brain works" or "nothing special."

This isn't a skills assessment. This is a stealth mission to catch yourself being competent when you're not looking.

What you'll get: A single prompt you paste into ChatGPT (free version works) that asks you 5 questions about your actual week - not your dream week, your REAL week. Then it names the skills you didn't know you were using.

The Stealth Skills Audit

What you'll need: 20-30 minutes, your favorite beverage, and permission to not sound impressive.

The moment you're after: That "wait, THAT'S a skill?" realization.

The things you do without thinking? Those are the things other people are Googling at 2am.

Time to check your pockets and see what you've been carrying around.

Here’s the PDF if you prefer.

ROCO Tip O’ the Week

Find What You Let Go Of (Before You Got "Practical")

You know that part of you that went quiet when adulthood got loud? The one who had interests, hobbies, ways of being that didn't "make sense" to keep doing?

This prompt helps you remember her.

Not so you can turn it into a business. Not so you can monetize your hobby. Just so you can see what you misplaced when you decided to be sensible.

Role

You are a thoughtful guide who helps people reconnect with parts of themselves they've set aside.

Objective

Help me remember activities, interests, or ways of being that I used to love but stopped doing when life got busy or I decided to be "practical."

Context

I'm in midlife/midcareer and I've spent years being responsible, sensible, doing what I "should" do. But there's a part of me that feels lost or dimmed. I want to remember what I used to do or love before I convinced myself it didn't matter or wasn't productive enough.

Ask me these questions ONE AT A TIME (wait for my answer before asking the next):

  1. What did you used to do in your free time that you don't do anymore?

  2. What activity made you lose track of time before you had to be "on" all the time?

  3. What did people compliment you on or ask you about that you brushed off as "just a hobby"?

  4. What did you stop doing because someone said it was impractical, silly, or wouldn't lead anywhere?

  5. If you had a completely free Saturday with no obligations and no one watching - what would younger-you have done?

Output

After I answer all 5 questions, show me:

  • The pattern of what I let go of (what type of activities/interests)

  • What these activities gave me that I might be missing now (creativity? flow? joy? connection?)

  • One small, low-pressure way I could try ONE of these things again - not as a project, just to see if it still fits

Make it feel like permission, not homework.

You are a thoughtful guide who helps people reconnect with parts of themselves they've set aside.

Help me remember activities, interests, or ways of being that I used to love but stopped doing when life got busy or I decided to be "practical."

I'm in midlife/midcareer and I've spent years being responsible, sensible, doing what I "should" do. But there's a part of me that feels lost or dimmed. I want to remember what I used to do or love before I convinced myself it didn't matter or wasn't productive enough.

Ask me these questions ONE AT A TIME (wait for my answer before asking the next):

What did you used to do in your free time that you don't do anymore? What activity made you lose track of time before you had to be "on" all the time? What did people compliment you on or ask you about that you brushed off as "just a hobby"? What did you stop doing because someone said it was impractical, silly, or wouldn't lead anywhere? If you had a completely free Saturday with no obligations and no one watching — what would younger-you have done?

After I answer all 5 questions, show me:

The pattern of what I let go of (what type of activities/interests) What these activities gave me that I might be missing now (creativity? flow? joy? connection?) One small, low-pressure way I could try ONE of these things again — not as a project, just to see if it still fits

Make it feel like permission, not homework.

Why this works: You're not being asked to justify why you stopped or prove it was worth keeping. You're just remembering. And sometimes remembering is the thing that shifts everything.

💡 Remember: If the output feels too gentle or not direct enough, tell ChatGPT. Say "be more direct" or "cut the therapy speak" - 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):

What’s coming up

AI Confidential: Confidence NOW

🗓 Tuesday, December 9th · 12 PM CST / 10 AM PT / 1 PM ET

Feeling behind on AI? You're not. You just haven't had a chance to practice.

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.

You'll learn:

  • What AI is (and isn't - it's a pattern-spotter, not a genius)

  • How to use the Shopping Mall Metaphor to pick tools without panic

  • How to master the ROCO Framework for clear, confident prompting

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

💜 Know someone drowning in tech overwhelm?

Send them this link. It’s a $30 transformation from panic to confidence - and yes, they’ll thank you later.

That’s it for this week.

You don't need to launch anything. You don't need to announce anything. You don't even need to know what comes next.

Just notice what you've been carrying. Just remember what you misplaced.

The rest can wait.

💜

Take care of yourself. Take care of each other.

Deb

P.S. If you used the Stealth Skills Audit or the remembering prompt this week and had an "oh shit" moment - hit reply and tell me. I want to hear what you found.

P.P.S. Forward this to someone who feels like they've lost themselves in the busy. Sometimes we just need permission to look for what's still there.

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