I Have a Team (A Collection of “Wherewithal Moments”)

I was sitting at my kitchen table over Thanksgiving, staring at the ceiling, thinking about my new book. (It comes out in November.) And I was spiraling.

My first book, Ideaflow, took twelve years of reading. Twelve years of dog-eared pages and highlighted passages and "I should remember this for later" notes that I half-forgot. A lot of that reading ended up in the manuscript, but most of those stories didn't stick in my head long-term. They went from my reading straight into the book. (True story: I actually paused reading the audiobook multiple times to take notes… on my own book. The director thought that was strange. But I can’t imagine any author is walking around with an entire book in their head!)

And now I needed to do that again. In a fraction of the time.

I kid you not, sitting there, I thought: how in the world am I going to pull this off?

And then I got up. Walked across the driveway to my office. Opened Claude Code. And I said: "Read my book proposal. Then assemble a research plan as if you had all the time in the world to thoroughly and exhaustively conduct research for each chapter."

It came back with a comprehensive plan. For each chapter.

Then I said: "Now commission sub-agents to execute each of these research plans."

And it did.

I ended up with 90 pages of research per chapter. Academic studies. Real-world examples. Counterarguments. Data I never would have found on my own — and certainly not in the time I had.

I'd been stuck for weeks. Not because the technology wasn't available. Because I hadn't thought to ask.

I've started calling moments like this "wherewithal moments." They're those flashes where you suddenly realize, mid-struggle, that you've been doing something alone that you didn't need to do alone. They're hard to manufacture. But they compound.

Last week I wrote about how we've grown accustomed to unassisted living — how the biggest barrier to becoming AI native isn't skill or access, but the deep conditioning of doing cognitive work alone. A few people wrote back and asked: "Okay, but how do you actually start to break that conditioning?"

Honestly? I'm still figuring it out. But I've had a handful of these wherewithal moments over the past year, and I thought it might be nice to share a few here.

300 Book Covers While I Was on Stage

This one's a little ridiculous.

I was in the car on the way to deliver a keynote on the east coast. And I had this thought: I really need to start exploring directions for the book cover. But I don't have time to sit down with a designer. I don't even know what I want yet.

So I pulled out my laptop — in the car, before I got to the venue — and opened Claude Code.

I said: "Pretend to be a graphic designer with extensive experience in book cover creative direction. Imagine 100 different creative directions for my book cover. Then, for each direction, write three different prompts for Gemini's image generation model. Then send those prompts to the model via API and save all the resulting images to a folder on my desktop."

Then I got out of the car and walked into the venue.

Here's the funny part: I wanted to preserve the connection so the agent could keep working. So I was walking around the client site with my laptop open, just... carrying it around like some kind of overeager intern. (I'm sure I looked ridiculous.)

I delivered the keynote. An hour later, I checked my desktop.

300 book cover concepts. Organized by creative direction. Total cost: $11.95 in API tokens.

Were most of them bad? Yes. Were some of them surprisingly interesting? Also yes. Did I have raw material to react to — to start discovering what I actually wanted? Absolutely.

The point isn't that AI generated my book cover. It didn't. The point is that I had a creative team working on my behalf while I was doing something else entirely.

The PR Agent I'd Been Ghosting

This one's embarrassing.

I work with a PR agent named Julie. Her job is to send me headlines and stories that I might want to comment on — opportunities to get quoted, to share a perspective, to stay visible.

For months, I'd been ghosting her.

Not because I didn't want to respond. Because I genuinely didn't have the bandwidth to give them the consideration they deserved. Every request required me to read the article, think about what I actually thought, figure out how to articulate it in a quotable way, and then write a response. That's 45 minutes minimum. And I was already underwater.

So I just... didn't respond. I felt bad about it. But I didn't have a solution.

Then one day, as I was in the middle of a 30-person workshop, I had an idea. Julie had sent me a batch of questions that morning. And I thought: wait.

I opened Claude Code on my laptop. (While facilitating. I know. The teams were doing group work ;-))

I said: "Read all my blog posts and call transcripts. Then read these questions from my PR agent. Craft three possible responses to each question, in my voice, with the kind of hooks that work for PR."

I checked back between workshop modules. Got three options for each question. Said "make them shorter — PR needs punchier hooks.” Copy, paste, send.

Total active time: maybe five minutes.

And I realized: That's ‘handmade artisanal Jeremy’ who doesn't have the bandwidth. With AI, Augmented-I DO have bandwidth.

I'd been operating as an individual contributor when I had a team available.

What I've Noticed

Here's what connects these moments — and why I think they matter more than any individual tactic:

Discomfort is the trigger. Every single one of these moments happened because I was stuck, failing, or overwhelmed. The research team emerged because I was drowning. The book covers happened because I had zero time. The PR thing happened because I'd been dropping the ball for months.

Nobody has a wherewithal moment while cruising. You have them when you're struggling. Which means — and this is the uncomfortable part — the feeling of being stuck is actually a signal. It's your cue to ask: "Am I doing this alone because I have to, or because I forgot I don't have to?"

Most of us interpret that discomfort as "I need to work harder." The reframe is: "I need to deploy my team."

You don't need an hour. You need five minutes of clarity. Not time to build some elaborate workflow. Just five minutes where you remember: I'm not an individual contributor. I have a team.

That's the wherewithal. And it's harder to come by than it sounds. Just this morning, I almost walked into my weekly Junto meeting — a cohort of practitioners I learn with — completely empty-handed. Five minutes before the call, I remembered. I opened two Claude Code windows, pointed both of them at different tasks, and by the time the meeting ended, I had five proposed article directions with supporting evidence pulled from my own conversations. Ninety minutes of work, compressed into five minutes of wherewithal.

I still almost forgot. The default is still to show up alone.

They compound. Every time I have one of these moments, it gets slightly easier to have the next one. The pattern recognition improves. The reflex develops. Not linearly — it's more like learning to notice a bird you'd never seen before. Once you see it once, you start seeing it everywhere.

I'm not there yet. I still forget constantly. But I forget slightly less than I did six months ago.

A Starting Point

If you want to start building this reflex, here's the smallest possible experiment:

Before your next meeting, ask yourself: "What could I have working while I'm away?"

Not "What could AI do for me?" — that's too abstract. "What could I have working while I'm away?"

It might be research on a topic you've been meaning to dig into. It might be drafting options for an email you've been avoiding. It might be analyzing a document you haven't had time to read.

And if you're not sure what to ask, try this — just paste it into Claude or ChatGPT before your next meeting:

"I have 45 minutes in a meeting. While I'm gone, I'd like you to [describe the task]. When I come back, have three options ready for me to react to."

The task doesn't have to be perfect. The prompt doesn't have to be clever. You just have to remember that you have a team.

And then deploy them.

Related: Do You Feel the Pain of Idle Agents?
Related: You're a Manager Now (But Most Don't Know It)
Related: Hit Reset
Related: Redefine AI

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