Hard Lessons from the AI Trenches

Living in AI First Mode: Hard Lessons from the Last Mile

For the past two weeks, I’ve been living in AI first mode. Letting AI take the first stab at everything I do. Not just reading about it or watching demos, but truly building, testing, failing, and learning with it.

Here’s the truth. While the world is raving about how powerful AI is, we need to talk about where not to waste your time.

I assumed AI would take care of the mundane so I could focus on what I do best — thinking, creating value, designing experiences, writing points of view. But surprise. AI wants to do my job, the fun part, and leave me with the chores it can’t quite handle yet. Let me explain.

Creating value happens in the first 45 minutes. Outlining a curriculum, drafting a long-form essay, sketching a concept. AI handles that beautifully. But the last mile? Stitching it all together, refining, formatting, applying judgment and taste? That’s where AI collapses. Painfully.

Yesterday, after a solid 45-minute brainstorming session, we had a great 70 percent draft. But then came the styling, sequencing, formatting. AI just couldn’t do it. Four hours later, I was still nudging it along. It couldn’t lift a finger on that last stretch. As a designer, I can do it in minutes. But I find it boring. Still, I have to do it. Because AI simply isn’t built for that yet.

Why? Because the last mile requires coordination, distributed cognition, and human nuance. It’s about connecting meaning, not just producing output. So here’s my advice. Don’t waste time using AI for the last mile. Save your energy. Trust me.

I now work with 10 AI minions. I feed them the same prompt to see who performs best. It’s not about one perfect AI. It’s about orchestrating many. But here’s the thing. Never throw a complex task at them all at once to any model. AI struggles with stitching. Break it down. Handhold it. Feed it step by step. And you do the synthesis.

Because collaborating with AI is a skill. An advanced one.
As a cognitive science nerd, I get it. AI is brilliant at generating the next best word, image, or sentence based on its training. But don’t expect it to think like you. Don’t expect it to reason, search, or format like you. That’s not what generative AI does. It generates. Period.

So here’s the playbook.
Don’t delegate complexity
Break down tasks
Use AI for creative starts
Stitch the final outcome yourself

I’m writing a guide titled "Collaborating with AI" — a practical survival kit for creators, builders, and thinkers navigating this new world. It will be available on May 31. I hope it helps you save thousands of hours.

Until then, collaborate with curiosity. And never delegate the last mile.