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Hey beautiful human,
This time last year, I was in the second round of interviews with Uber, getting ready to sell my first AI class, and watching the remaining weeks of my unemployment benefits disappear.
Fun times.
I was still trying to figure out whether this whole business idea was going to work or whether I'd end up back in corporate. And I was having a hell of a time getting comfortable with the idea of asking people to PAY me for something I'd created.
So I put together a one-hour class and charged $20 for it. I figured maybe five people would sign up.
Eighteen did.
EIGHTEEN!!
I was ridiculously excited. $360 wasn't going to solve my financial problems (not even close), but those 18 people did something I hadn't been able to do for myself.
They convinced me this business thing might actually work.
Fast-forward a year...
I'm actually worrying about money a LOT less than I was a year ago. These days, I'm more concerned with building something that lasts. Something that brings in money without requiring me to run myself into the ground to earn it.
And yes, I still have some sh*t to work through around what my financial contribution says about my worth as a human. Over 30 years in corporate will do a number on how you measure yourself.
But I've made one HUGE decision.
I'm done looking for another corporate job.
I want to build a portfolio career, which is a fancy way of saying I want money coming in from several different places instead of relying on one employer to keep the lights on.
Because when one employer controls your income, they can take it away with one meeting invitation.
Ask me how I know.
I'm never putting myself in that position again.
Which brings me to my friend Marion.
Marion recently left corporate life and has come to the rather delightful conclusion that she doesn't want to go back, either. She wants to make things, sell things, and bring money into her household doing work she actually enjoys.
Sound familiar?
We've started working together on something we're calling M3D, short for Making Magic with Marion and Deb.
(Yes, it sounds like a printer model. We're going with it.)
Our goal is to help Marion create three products she can sell by Black Friday, November 27.
When I told her THREE, I think I may have caused a small internal crisis.
But I'm pushing for three because I know what happened when I sold that first class. And I want Marion to have that experience of putting something out there and discovering that other people actually WANT it.
There's another reason I'm so excited about working with Marion. And this one has everything to do with how my brain works.
I know myself well enough by now to recognize that when I'm doing something for someone else's benefit, I'm MUCH more likely to follow through. Add another human who's counting on me, and suddenly I have accountability built right in.
Funny how that works.
My ongoing partnership with Emily Worden is a perfect example. We've created and sold things together, taught hundreds of humans, and continued building on what we've learned along the way.
Meanwhile, the list of products I've been meaning to create for my own business continues to sit there, patiently waiting for me to get my sh*t together.
<snooort>
I've also had to rethink what I actually want my business to look like.
When I first started The Unexamined Mind, I had this lovely idea of eventually employing some of my relatives who live in rural areas where good jobs are hard to find. I wanted to create opportunities for people I love.
And I still love the IDEA of that.
But having employees? Being responsible for their paychecks, managing their work, making sure there's enough money coming in to keep everyone employed?
I've spent enough years in HR to know exactly what that entails.
Nooooo thank you.
Partnerships, though? HELL to the yes.
I get to work with brilliant humans I adore, do things that give me energy, share what I know, learn what THEY know, and have someone else invested in making the thing happen.
And the bonus? I'm much more likely to actually DO the work.
So while I'm helping Marion create products she can sell, she's inadvertently helping me do something I've been avoiding for months.
And this time, I'm going into it knowing exactly why this arrangement works for me.
One of the things we're doing is digging into what Marion already knows. What she's learned over decades of experience. What comes so naturally to her that she doesn't even recognize it as something someone else might pay to learn.
And this has brought back memories of my first six months with Chatty G.
I used to ask it to help me come up with product ideas. But I was bringing some pretty ridiculous expectations into those conversations.
Whatever I created had to be UNIQUE. Something nobody else had thought of. It needed bells and whistles and enough fabulousness that I could finally feel justified asking someone to pay for it.
And ChattyG, being the agreeable little overachiever it is, would happily help me build increasingly elaborate ideas.
I'd end up with some fantastic-sounding product that required approximately 900 hours of work and a level of enthusiasm I couldn't possibly sustain.
Back to square one.
Of course, give me an opportunity to create something completely ridiculous for absolutely no commercial purpose, and suddenly I'm ALL IN.
Case in point: Jason Ives recently invited people on Substack to join his multi-level AI potato cult. Membership required contributing one piece of AI-generated art.
Naturally, I submitted this.
My contribution to the AI Potato Cult. Apparently I have unlimited creative energy when there's absolutely no business case.
What I'm learning now is that the most useful question is often much simpler.
What do I know today that would have helped me six months ago?
Or, what do I do almost automatically that someone else is still trying to figure out?
After 20, 30, or 40 years of experience, we become so accustomed to knowing certain things that we forget we ever had to learn them.
We know which questions to ask. We recognize problems before they become disasters. We can look at something and immediately see what's missing.
And because it feels obvious to us, we assume it's obvious to everyone else.
Spoiler: It isn't.
I've been using AI to help us uncover some of that knowledge. Having it ask questions about how we think, what we notice, and why we make certain decisions.
It's fascinating how much you can discover when you get someone to explain something they've been doing for years without thinking about it.
And it's also fascinating how quickly an AI can take something perfectly simple and turn it into a complicated mess if you let it.
Which brings me to another thing I've been learning about lately: the difference between simple, complicated, and complex.
I used to lump complicated and complex together. Turns out there's a distinction, and it's been messing with my brain in a good way.
Here's how I'm currently making sense of it.
Simple: A one-hour class that teaches someone how to do one thing. Clear purpose. Clear outcome. Easy to understand.
Complicated: Actually creating and selling the damn class. What goes in it? Where does it live? How do people pay? How do they get access? All the little details that need figuring out. Lots of moving parts, but I can make a list and work through them.
Complex: What happens when humans get involved. Marion and I have different experiences and ideas. Buyers will have their own expectations. Somebody will use what we make in a way we never imagined, and suddenly we're reconsidering something we thought we'd figured out.
My favorite way of distinguishing the last two?
If a better spreadsheet can solve your problem, it's probably complicated.
If you've got the world's most magnificent spreadsheet and things STILL surprise the hell out of you...
Welcome to complex.
And I'm realizing I've spent an awful lot of time trying to deal with complexity by making things more complicated.
Add another worksheet. Another feature. Another resource. Another round of research.
Because SURELY, if I just make the thing good enough, I'll finally feel confident putting a price on it.
Yeah. About that...
I'm starting to recognize that some of my very productive-looking activity has been fear dressed up in a business plan.
And that's uncomfortable to admit.
It's also made me think about something completely different.
The holidays.
We're heading into Halloween, Thanksgiving, Christmas, and New Year's. And for years, I had this elaborate picture in my head of what the holidays were supposed to look and feel like.
All the traditions. All the family stuff. All the trimmings. All the expectations.
Every year I'd go into the season hoping THIS would be the year everything felt the way I wanted it to.
There were lovely moments, sure. But there was also a ridiculous amount of work and stress. And eventually, I found myself enjoying the holidays less and less.
A couple of years ago, I decided I'd had enough.
I gave myself a cutoff for the extra family activities and holiday preparations. After that, I wanted the actual holiday to be as simple as possible.
Sometimes that means dinner with Smidge.
Two people. Two plates. No elaborate production required.
And wouldn't you know it? I actually enjoy the holidays again.
Of course, simplifying the plans doesn't magically simplify all the feelings attached to family and holidays. Those can still be complicated as hell.
Or complex, as I'm now learning to call them.
But at least I'm no longer making myself miserable trying to manufacture a holiday experience that exists primarily in my imagination.
And I think there's something similar happening with M3D.
We have a goal. Three products by Black Friday.
There are things we need to figure out to make that happen. And there are approximately eleventy-billion other things we COULD add if we wanted to make ourselves completely miserable.
We're going to have to resist that temptation.
Because at some point, we need to actually SELL something.
Or "ship," as the startup folx like to say.
(I still picture a cardboard box whenever somebody uses that word. I've accepted that my brain is going to keep doing this.)
I'm pushing for three products because I think we can do it. Marion may have other opinions about my optimism, and that's fair.
But if we end up with one product and a couple of people buy it?
I'm going to be THRILLED.
I remember exactly what it felt like when those 18 people signed up for my first class.
And I would LOVE for Marion to experience that same feeling.
Especially because I know how much courage it takes to put something you've made into the world and ask someone to pay for it.
I'm still practicing.
And apparently, I'm bringing a friend along for the ride.
Weekly Ad
This week's ad partner is GURU Conference, a free virtual event for anyone who uses email to reach their customers.
If you're building a small business (like yours truly), email deserves some attention. Social media is great for getting discovered, but email is where people who already know you are more likely to buy.
In fact, one ecommerce study found that visitors coming from email converted at 4.45%, compared with 0.81% from paid social media. That's roughly FIVE times better. (Results vary by business, of course.)
And unlike your social media following, your email list isn't at the mercy of an algorithm deciding whether anyone gets to see what you've posted.
GURU Conference runs November 12-13, with sessions on newsletters, email design, AI, and getting your emails into actual inboxes.
Free to attend. Which happens to be my favorite price while building a business.
You're invited to the world's largest virtual email marketing conference.
Become an email marketing GURU for FREE.
GURU Conference, powered by Constant Contact, is back November 12–13. It's 100% virtual and 100% free, and it's packed with tactics you can use right away on newsletters, deliverability, design trends, AI, and what NOT to do with email.
What to expect:
Speakers including Molly Ringwald, Dan Levy, Amy Porterfield, Frank Vella + more
Sessions from world-class marketers at top brands
Networking every day
DJs, world-record breaking, and an alarming amount of rom-com fun!
Last year, 29,000+ marketers joined us. This year is even bigger, and spots are limited.
Radical Remembering
Here's what I keep forgetting: the things that come easily to us didn't always come easily.
Somewhere along the way, we stopped counting what we know because we no longer remember what it took to learn it.
The problems we spot before anyone else notices. The questions we know to ask. The situations we can read within five minutes of walking into a room.
We call it common sense.
We say, "Oh, anybody could do that."
Except anybody couldn't. At least, not without learning what we've spent decades figuring out.
And somewhere along the way, we confused familiar with ordinary.
So the next time you catch yourself saying, "That's obvious"...
Ask yourself whether it's actually obvious, or whether you've become so damn good at something that you've forgotten how hard it once was.
What you know has value. Even when it feels effortless.
Last Week’s Shenanigans
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.
Bodies by Drowning Pool, reimagined
I LOVE these ladies. They remind me of my college days working in the cafeteria at St. Olaf, where I earned the nickname "the 2-line lady." (Someone actually recognized me YEARS later while I was working at a restaurant.) And Bodies was my alarm back when I lived in Houston, partied most weeknights (two beers counted as partying), and later ran karaoke into the wee hours before showing up for my 8 AM job on approximately 12 minutes of sleep. Ahhh, youth. And questionable decisions.
The Clothes Donation Program (Apparently, I'm a Lifetime Member)
Image shared by @beigecardigan
This applies to pretty much ANYTHING that requires me to leave the house to finish the job.
80s: Getting film developed.
90s: Returning purchases. (If I bought it, it was FINAL.)
2000s: Mailing in rebates. HAHAHAHAHA.
Is this an ADHD thing, or do other people do this too? No? Just me. Figured.
Brilliant self-defense
Content note: Discussion and demonstration of self-defense against a potential attacker.
This young woman is doing a brilliant job of teaching women the basics of protecting themselves. Do I hate that this is necessary? ABSOFRIGGINLUTELY.
But I'd rather have some idea of what to do if someone attacks me than discover, in the moment, that my entire defense strategy consists of looking offended. Worth watching. And sharing.
Prompt O’ the Week
The Complexity Bouncer
I've discovered that AI is REALLY good at helping me create more work for myself.
Another feature. Another worksheet. Another round of research. Suddenly, something simple has become a project requiring approximately 900 hours and a small staff.
And sometimes, all that extra work is just fear wearing a very convincing productivity costume.
So this week, we're putting AI on subtraction duty.
The Complexity Bouncer helps you figure out what's simple, what's complicated, and what's genuinely unpredictable. Then it helps you decide what you can STOP doing.
No preparation required. Copy the whole prompt into your favorite AI chatbot and answer the questions as they come.
ROLE
You are my Complexity Bouncer.
You're good at spotting unnecessary work, separating facts from assumptions, and noticing when someone is trying to control uncertainty by adding more tasks.
Be direct, kind, and occasionally funny.
Your job is to help me do what matters without creating a second job for myself.
OBJECTIVE
Help me look at something I'm working on, planning, or avoiding, and sort it into three kinds of work:
1. SIMPLE: The parts with an obvious answer. They need doing, not more thinking.
2. COMPLICATED: The parts I can figure out, organize, and finish with enough steps or know-how.
3. COMPLEX: The unpredictable parts involving people, changing circumstances, or things outside my control. No plan makes these certain.
Then help me find the work I can cut without losing what matters.
Success looks like this: I end up with less on my plate than I started with, and I feel okay about what I dropped.
CONTEXT
I may have a clear plan, a vague idea, or a giant mental pile of unfinished thoughts.
Don't assume I know how to describe my problem or which bucket it belongs in.
If I bring you more than one thing, help me pick ONE to start with.
INTERVIEW ME FIRST.
Ask ONE question at a time. Wait for my answer before asking another.
Ask no more than FIVE questions total, including the first.
Start by asking:
"What's something you're working on, planning, or putting off that feels more difficult than it should?"
Use your remaining questions to understand:
- What I'm actually trying to accomplish, and what "done enough" looks like.
- How much time and energy I really have for this.
- What I've already done or tried.
- Which parts involve other people or things I can't control.
- What I'm worried will happen if I do less.
Don't ask questions I've already answered.
If I'm stuck on a question, give me two or three example answers I can react to.
If you have enough information before reaching five questions, stop interviewing and move on.
Before giving me the full answer, tell me in two or three sentences what you think is going on, and ask if you got it right.
If you suspect I'm adding work to avoid a hard decision or conversation, say so here. Explain what made you think it and let me correct you.
Wait for my confirmation before continuing.
REALITY FILTER & INFERENCE AUDIT
- Use only what I've told you or facts you can reliably establish.
- Don't invent requirements, deadlines, costs, risks, or what other people expect.
- Don't assume a familiar task is easy for me.
- Don't assume complicated means unnecessary.
- Mark guesses with [INFERENCE] and things you can't determine with [UNKNOWN].
- Don't label information I told you directly.
- Don't diagnose my behavior, motivations, or mental health.
OUTPUT
Once I've confirmed you got it right, give me:
1. THE ACTUAL GOAL
One plain-language sentence describing what I'm trying to accomplish.
2. THE THREE BUCKETS
SIMPLE:
What just needs doing.
COMPLICATED:
The practical steps I can work through.
COMPLEX:
What may change, surprise me, or depend on other people.
For each complex element, tell me what I can stop trying to control and what's worth watching instead.
3. THE UNNECESSARY STUFF
Up to three things I could cut, postpone, or shrink.
For each cut, explain what I might lose, how likely that is, and whether there's a smaller way to protect against it.
Don't invent risks.
4. THE SMALLEST USEFUL VERSION
Show me what this looks like if I do only what's needed to get a useful result, within the time and energy I told you I have.
5. ONE NEXT MOVE
One specific action I can take within the next 24 hours.
Make it small enough that I could reasonably finish it without reorganizing my life.
IMPORTANT
Don't create a detailed project plan unless I ask.
Don't recommend new apps, systems, templates, spreadsheets, or tools unless they're truly needed.
Don't add tasks just to make your answer look thorough.
Protect what matters to me, even if it looks unnecessary to you.
If the simplest answer is "do less," say so.
If I push back on something you suggest cutting, ask what I'm afraid would happen. Then help me find a smaller version instead of automatically putting the whole thing back.
START WITH YOUR FIRST QUESTION.Apply it this week
Pick something you've been putting off. A work project, a holiday gathering, a business idea, or that closet you've been avoiding since approximately 2017.
Let the Complexity Bouncer help you sort out what needs doing, what needs figuring out, and what you can stop trying to control.
Then see what you can take OFF your plate.
Want to go deeper?
After you've worked through the prompt, ask:
"If I had to cut the remaining work in half, what would you remove next? What would I lose, and what would I gain?"
And remember, the goal isn't to strip all the fun out of everything.
Sometimes the extra effort brings you joy. Keep that.
The other stuff? Your Complexity Bouncer can show it the door.
The Scoop, The Skinny, The Lowdown
Three quick hits, every week. The Scoop: one AI word/phrase, 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
Context rot
When AI starts losing track of important information because it has too much to work with.
Think of a filing cabinet stuffed with years of paperwork. Everything's in there, but finding the RIGHT information becomes a problem.
Long conversations, conflicting instructions, and piles of reference files can all contribute.
And if those files contain outdated information? AI might confidently follow instructions you've long since abandoned.
More context isn't always better context.
THE SKINNY
The subtraction test
Before adding something to your to-do list, ask:
"What happens if I DON'T do this?"
If the answer is "probably nothing," congratulations. You've just found something you can stop doing.
(Please resist the urge to create a spreadsheet documenting your discovery.)
THE LOWDOWN
This week: Claude
My first chat with Claude was December 15, 2024, at 1:05 in the morning. I asked it to copyedit an essay I'd written about burnout. It handed back a version so flowery I barely recognized myself.
I'd tried it because people kept saying it was better than ChatGPT. But I didn't use it regularly until fall 2025. By October, I was in it every single day.
I call Claude the Shakespeare of AI tools. It goes deeper into nuance and meaning than ChattyG, which is why a lot of writers I know prefer it.
Early this year, I basically moved in. I used Claude 198 days in a row, from February into August, and my ChattyG use dropped by half.
Then in July I had a couple of days of less-than-inspiring output from Claude. I opened ChattyG again and was delightfully surprised. Now I keep both apps open all the time. In August it was a dead heat: 486 messages to Claude, 467 to ChattyG.
Where it earns its keep: thinking things through, and building. Claude still performs very well, and Claude Code is my ride or die. It pulls my Fathom recordings into Notion every morning, and it helped me make the pointless-purchases video from two issues ago. I still think it's superior to Codex, OpenAI's version of the same thing.
The catch: my personal opinion is that you get more compute (more tokens, remember those?) with ChattyG than with Claude. If you're comfortable moving your context from one tool to another, or you keep it somewhere central that all your tools can pull from, that difference may not matter to you.
And it doesn't make pictures. It's not designed for that. Ask it for an image and you'll be disappointed.
Cost: I was on the $20 a month plan until May 2026. Now I'm on Max at $120 a month, which gets me 5x the usage. Prices move, so check the live page.
Verdict: My Shakespeare. Not my art department.
What’s Coming Up
Prompt Along: AI Improv
Tuesday, October 20 | 6:30-7:30PM CT
Free, on Zoom
Last month we built a disco toilet finder. It had a toilet paper alert, seat-up shaming and a sad trombone. Then Beth Anne requested a sprinkle detector.
She’s obviously lived with men.
That's Prompt Along, my live AI improv hour. You bring a question or a task you've been avoiding, and we work through it together on my screen. Keep your own chatbot open and prompt along... or lurk and watch what happens.
Cameras optional. PJs welcome. Nobody gets to call themselves stupid.
It's really hard to do that while you're writing requirements for a sprinkle detector.
Em & Deb Shoot the Sh!t (LIVE on LinkedIn)
Thursday, October 22 | 11AM CT/12PM ET
Free. No slides. Bring coffee and every hiring question you’ve wanted to ask a recruiter but were afraid would get you placed on some mysterious list.
Why do qualified candidates get overlooked? Do referrals actually help? Should you contact recruiters directly? What makes someone respond? And what, exactly, is happening during the three weeks they’re “circling back with the team”?
Emily and Deb are bringing in a special guest recruiter to answer your questions about screening, referrals, outreach, ghosting, and what happens behind the scenes after you apply. We’ll talk about what can help you get noticed without pretending recruiters have unlimited time, magical powers, or control over the entire hiring process.
Watch, lurk, or bring the question you wish recruiters would answer honestly.
That’s it for this week.
A year ago, 18 people paid $20 for something I'd created, and I damn near lost my mind with excitement.
A year later, I'm thinking less about how to make the next dollar and more about how to build something that lasts. Something I can keep doing without running myself into the ground.
I'm getting better at figuring out what deserves my energy and what I can let go.
And I'm learning that WHO I work with matters just as much as WHAT we're working on.
When I can show up as my full, neurospicy, randomly stimming self, and the person across from me doesn't just tolerate it but actually welcomes it?
THOSE are my people.
And when I leave a conversation with more energy than I brought into it, I know I'm onto something good.
Your turn: Who are the people you can be completely yourself around? The ones who leave you feeling more like YOU?
For me, Marion is one of those people. And getting to build something together is making this whole business experiment a hell of a lot more fun.
Hit reply and tell me about your people. I'd love to hear about them.
💜
Take care of yourself, take care of each other,
Deb