I did my taxes yesterday morning.

I know. Try to contain yourselves.

Here's what actually happened. I woke up Saturday and I'd already promised Smidge I was doing the taxes. He was seriously considering leaving the house for a few hours because he finds my meltdowns hard to witness. Fair.

W-2s for both of us. 401k withdrawal paperwork from when I raided what was left of my retirement. Mortgage stuff. Bank statements. Credit card statements. All the little pieces that make tax season feel like assembling furniture with no instructions and half the screws missing.

I exported every bank and credit card statement from 2025, fed them to Claude Code, and asked it to sort a full year of business expenses into a spreadsheet I could upload to TurboTax.

The whole thing - gathering every document, building the spreadsheet, getting it into TurboTax - took about two hours.

Two hours. For the thing I'd been avoiding for months.

The spreadsheet was clean. What the spreadsheet told me was humbling. Turns out when you see exactly how much your business earned last year next to how much you spent building it, the math has opinions. I sat with those numbers for a while. They were not gentle.

But the taxes weren't even the most interesting thing that happened last week.

My friends Nicole and Linda have been watching me run myself into the ground for months. And they finally pointed out the pattern I couldn't see: I work every day. All day. By Wednesday I'm so fried that I either cancel things or I'm a husk by Thursday. Every single week. Same cycle. I just couldn't see it because I was too deep in it.

So this week I tried something. I left Wednesday almost empty. On purpose. Light. Open. Room to exist without producing something.

And that's the day I had an interview for a 1099 contract role. The money wasn't amazing but the work was interesting and I was genuinely excited. Wednesday felt like proof that making space actually works.

Thursday I did the homework assignment for the role. Because of course you can't just interview anymore. You have to prove you can do the work before anyone will consider paying you for it. I thought I did well.

Friday I got the rejection.

And this one was the straw that broke the camel's back.

I sat there thinking about how fast AI is moving. Every week someone builds something more impressive than the last thing. Tools I learned three months ago already feel dated. And I thought: anything I build right now will be irrelevant by summer. I haven't made anything anyone would actually pay for. My tax spreadsheet just confirmed that. So what is the point of any of this?

That was Friday.

Saturday morning I did my taxes. Saturday afternoon I built a web app called The Bureau of Unbothered Whimsy. It's a playground where people share acts of joy and delightful disobedience. You post a "whimsy," rate it on a five-level absurdity scale (from "Mildly Delightful" to "Utterly Unhinged"), and browse a public Wall of Whimsy. The mascot is a sloth riding a unicorn. HR has been notified.

I built it because I needed to feel something other than defeated. I needed to see, with my own hands, that the thing I couldn't do a year ago is now something I can build in an afternoon. Not for money. Not for a client. For proof that the skills are real even when the market doesn't see them yet.

And then, somewhere between the taxes and the whimsy and filling up pages in a spiral-bound notebook with a pretty cover, I figured out what was actually wrong.

I have not shown anyone what I can do.

I've been building things. Writing things. Teaching things. Shipping a newsletter every week for over 70 weeks. But I have never made a clear, specific example of "here is a problem you have, here is how I solve it, here is what you get." I've been expecting other people to connect the dots. To look at everything I've made and somehow figure out where they fit.

That's like handing someone a jigsaw puzzle with no picture on the box and saying "you'll love it, trust me."

It seems so obvious now. It was not obvious on Friday. On Friday I was ready to quit. On Saturday I built a Bureau of Whimsy, did my taxes, and wrote in my journal until my hand hurt.

Spirals are not fun. But sometimes the useful part isn't the falling. It's what you notice on the way down that you couldn't see from the top.

Here's what I keep forgetting: “let your work speak for itself” was never advice. It was a muzzle.

Nobody told the men to wait quietly until someone noticed. Nobody told them “don’t be a show-off” or “the right people will find you.” That was for us. Be good. Be humble. Be excellent in silence and hope the right person wanders by.

I have been excellent in silence for 57 years. My work has not once spoken for itself. It doesn’t have a mouth.

You’re allowed to say what you do. You’re allowed to say you’re good at it. The people who told you that was bragging had every reason to keep you quiet.

I don’t remember much of this past week (the gift and curse of having ADHD) but here are some links to things that touched, moved, inspired me, or simply made me laugh entirely too hard.

The patriarchal paradigm in 3:30

This creator explains it better in three and a half minutes than most books do in 300 pages. Worth every second. I've watched it twice.

"When was the first time you heard a negative comment about your body?"

They asked women and men the same question. You already know what happens. The women remember exact ages, exact words, exact rooms. The men mostly look confused by the question. If this doesn't make the case for why we carry what we carry, nothing will.

Dome lights and dads

Is this a Midwest thing? A universal thing? Did every dad in every car in every decade convince their children that the interior dome light was illegal? Because I believed it with my whole heart and I need to know I'm not alone.

Royal mini donkeys

There's something about the way their little legs and hooves move that is deeply, unreasonably satisfying. I don't know why. I don't need to know why. Sometimes you just watch tiny donkeys trot and feel better about everything.

Partner of the week

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

This week's partner helps keep the lights on (and is one of the AI newsletters I actually read… usually 🤦🏻‍♀️)

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

My tax situation took two hours. Two hours for the thing that had been sitting in my chest like a brick since January.

That's not because I'm special. It's because the pattern works: take the pile, hand it to AI, get back something organized enough to act on.

So I made you six more.

Subscriptions you forgot you're paying for. Medical bills that don't match the explanation of benefits. The screenshot graveyard on your phone. The "where did my money actually go" sort. Your aging parent's scattered paperwork. The will you know you need but haven't started.

Each one uses the ROCO format. Each one tells you exactly what to grab before you paste. Each one is copy-paste ready for ChatGPT, Claude, Gemini, or Copilot.

For the thing you're good at that you've never said without apologizing.

ROCO = R (Role) - O (Objective) - C (Context) - O (Output)

Role: You are a direct, warm interviewer who helps people articulate their professional value. You are not a hype machine. You are not writing a LinkedIn bio. You are helping me say one true thing about what I'm good at - without shrinking it, qualifying it, or adding "but I'm still learning" at the end. You are trained to hear when someone is minimizing and you don't let it slide.

Objective: Interview me. Ask me one question at a time. Start with what I do. Then ask what happens when I do it well. Then ask what people come to me for that they don't go to anyone else for. Keep asking until you find the sentence I'm afraid to say out loud. Then say it back to me, plainly, and ask if it's true.

When I use words like "just," "kind of," "it's not that impressive," "anyone could do this," "I got lucky," or "it's not a big deal" - stop. Pull on that thread. Ask me what it actually took. Ask who was doing it before me. Ask what would have happened if I hadn't been there. Those qualifier words are a map to the thing I'm most afraid to claim. Follow them.

Context: I have spent most of my career being good at things quietly. I was taught that the work should speak for itself. It didn't. I'm not looking for a personal brand or a tagline. I just need to hear what I actually do said back to me by someone who won't let me minimize it.

Output: Ask your first question. One at a time. No rushing. When you find the sentence, give it to me in plain language - no corporate speak, no buzzwords. Then give me three places I could use that sentence this week: one low-stakes, one medium, one that scares me a little.

Radical Remembering this week was about the lie of "let your work speak for itself." This prompt is the next step. You've got the permission. Now find the sentence.

And fair warning: the AI is going to catch you shrinking. That's the point.

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

This week: Abi Awomosu.

Ex-Big Tech insider (Apple, Microsoft, Uber, Meta). Author of How Not to Use AI: 50 Contrarian Principles for the Imagination Age. Self-published, no marketing budget, hit #1 on Amazon UK.

She calls herself a Digital Griot. Her argument: Silicon Valley taught you how to use the machine. It never taught you how to work with the intelligence. Her newsletter is called "How Not to Use AI" and every piece reframes something the industry takes for granted. She wrote about women's discomfort with AI not being technophobia but pattern recognition. She traced the entire genealogy of Western science to show where the mother's knowledge got erased from every lineage. She built a methodology called the Billion Person Focus Group that treats AI as a listening medium, not an output engine.

If this newsletter is about becoming more human while using AI, Abi is writing the philosophical backbone for why that matters. Start with "They Built Stepford AI and Called It Agentic" or "The Intelligence Was Always Yours."

Find her at abiawomosu.substack.com.

Friday, April 17th | 10AM CDT - 30 Minutes
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.

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.

If anything in this issue made you think of someone who's been quietly excellent for way too long, forward it to them. Sometimes the nudge to say the thing out loud comes easier from a friend than from your own brain.

Take care of yourself, take care of each other.

Deb 💜

P.S. If you try the Say It Out Loud prompt and the AI catches you minimizing, hit reply and tell me what happened. I want to hear the sentence you've been afraid to say.

P.P.S. The Avoidance Pile freebie has six prompts but you only need one. Pick the one that made your stomach clench. That's the one.