I Spent Two Hours Herding AI. I Could Have Just Done It Myself.

Let me start by saying we genuinely love GetOut. We were Pogo Pass loyalists — the kind of people who had it auto-renewed and actually used it. So when Pogo Pass merged with GetOutPass to become GetOut in February 2026, we were cautiously optimistic. New name, bigger venue network, same idea: pay once, play all year. We’re in.

So I did what any modern parent with too much on his plate does: I handed the planning to Claude.

Two hours later, I had a spreadsheet. It was wrong.

The Herding Problem

Here’s what nobody tells you about using AI for anything more than a simple task: one correction creates another. You catch a mistake, fix it, and the fix introduces a new assumption. That assumption quietly breaks something else two steps down. You catch that, fix it — and now you’re back at the top of the loop.

I wasn’t using AI. I was managing it. There’s a difference.

Wrong venues. Wrong age assumptions — my wife paints, she’s an adult, Cordovan Art School is not exclusively for children, and yet there we were. Misread priorities. Placeholder text where real addresses should have been. Each correction was a conversation. Each conversation required me to explain context the AI should have already had. Rinse, repeat, two hours gone.

And the confidence. That’s the part that gets me every time. AI doesn’t say “I’m not sure about this.” It presents a finished-looking wrong answer and waits for you to catch it. If you don’t know what you’re looking at, you won’t.

One thing that did genuinely surprise me: when I asked why it couldn’t just scrape the GetOut website for addresses, Claude told me the site’s robots.txt blocked automated access — and then it actually respected that. Didn’t try to work around it. Just explained and moved on. I assumed AI would barrel through the internet like a golden retriever that doesn’t see fences. Turns out there are guardrails. Small win, noted.

But that was one moment in two hours of cattle-driving.

This Keeps Happening

It’s not just this session. The more I use AI for anything involving a real document, real planning, or real decisions, the more I find myself doing exactly this — nudging, correcting, re-explaining, catching assumptions I didn’t know I’d need to catch. The output looks polished. The content needs work. And the gap between those two things is my time.

I could have built that spreadsheet myself in 90 minutes. It would have been right the first time because I would have read the document myself.

But GetOut? Still Great.

All of this is about the AI, not the passes. GetOut — the thing that grew out of our beloved Pogo Pass — is genuinely worth it. The venues are real, the value is real, and we’re going to have a great year with it.

We’ll just be doing the planning ourselves.