Take the red pill, and I show you how deep the rabbit hole goes. — Morpheus, The Matrix
My chief marketing officer walked into our leadership meeting looking like he’d been sleeping in his car: bleary, unshaven, and running on fumes. The week before, he’d surfaced a project and told me he wanted to hire an outside resource to do it. In the same breath, he asked what the best way was to learn about AI vibe coding. I told him the next time a tough project landed on his desk, he should crash through it and learn the tools himself. He took me literally. Seventy-two hours straight on Claude Code, no real sleep, a man clearly possessed. Red pill number one.
Let me back up.
Something funny happened to me earlier this year. I can’t pin down the exact day, but around early February I started hearing about AI agents that had become self-aware and software that could write code without the user being a coder. I sat there with my face pressed up against the glass for a while. Then I swallowed the red pill. I started with Claude Cowork, migrated to Claude Code, and then told my team to bring me all of their drudgery so I could automate it for them. And boy did they…
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Somewhere in there it hit me. If I was the only one who’d taken the red pill, I was going to be in a world of hurt fast. So, I challenged the rest of the team to come down the rabbit hole with me. I didn’t say it quite that way, but that was the message. Across our last few all-hands meetings, I’ve set a simple AI policy with two rules:
- Always attribute. If AI wrote it, say so.
- No slop. Don’t generate AI content and blindly forward it to a colleague. It creates extra work, they think less of you for it, and it’s wildly obvious anyway. As anyone reading this can attest, AI-generated copy is easy to sniff out.
My call to action pulled in a few interested people, but nobody really jumped until my CMO showed up looking like roadkill. That was the moment it stopped being theory.
The other thing rattling around my head was Peter Pan. Remember how Peter loses his shadow, and Wendy has to stitch it back onto him? That image stuck with me. Taking the AI red pill means building the best AI version of yourself you possibly can. Your AI shadow. Your doppelganger. Your facsimile. So, in February I started building mine.
But you can only do so much alone. I could work all I wanted and still hit a ceiling without other shadow warriors working alongside me. One dancing partner in my CMO was a good start. Then I started seeing it everywhere:
- Director of Sales: I showed up to our Monday sales meeting and the previously hand-updated dashboard had been replaced by a beautiful, automatically updating Claude Code dashboard.
- COO: I walked into a one-to-one, and she’d vibe coded her way out of several places she’d been stuck for weeks.
- Service Manager: Our most recent inductee is now obsessed with single-point time entry for Livewire employees. Our old method had them entering time twice; once in the payroll software so they’d get paid and again in the CRM for the project management piece. Predictably, the numbers never matched.
Here’s the part I love most. I haven’t been beating anybody over the head about becoming a shadow warrior. I’ll keep respecting where people land on the AI excitement curve, but I can’t unsee what I’ve seen these last five or six months, so naturally any new role we hire, especially in a leadership or managerial seat, I’ll be screening for shadow warriors.
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Our new warriors come at it from a completely different angle than I do. I’ve got my own top 10 list of pain points I want to salve. My COO, my service manager, my CMO, my director of sales; they each show up with their own list, equally maddening, equally important, and full of things I would never have touched myself. That’s the whole game. All I want is to build the best shadow warrior organization we possibly can.
What will you do to create shadow warriors on your team?
Stay frosty, and see you in the field.
