Why AI Outputs Feel Empty Even When They're Good


The summer solstice passed last Sunday.

It's the natural midpoint of the year, and I've been using it as a prompt to check in with myself on how 2026 is going.

In my upcoming book Life in Perspective, I write about the value of a mid-year review. A few of the questions I sit with:

  • What have I learned from my endeavors so far this year?
  • Which assumptions I started the year with turned out to be wrong?
  • What do I want to make sure I get to before December?

If you have a few minutes this week, I'd encourage you to sit with at least one of them.


Every Folder on My Computer (Full Reveal)

This week, I'm showing you my real file setup, every folder on my computer.

It's simpler than you'd expect, and it's the reason I can point AI at the exact part of my work I need and move through it in minutes instead of hours.

I'll walk you through the whole thing, folder by folder.


Why AI Outputs Feel Empty Even When They're Good

Something I've noticed working with AI: you can get a genuinely good result and still feel nothing about it.

An HTML dashboard, a consulting proposal, a travel itinerary. The AI built it. It might even be well-done. But there's no commitment there, no real belief in it. You're not sure if you'd stand behind it, which means you probably just set it aside and never come back to it.

Working through the process of creating something does something invisible: it builds your relationship to the thing you're making. Each decision point, each moment of stopping to ask whether you're on the right track, adds up. By the time you're done, you trust the output because you were there for every step of it.

When AI skips all of that, the artifact just appears out of nowhere. And an artifact that just appears is one you have no real stake in.

This is part of why I started staying more present in the process rather than handing it off entirely. If I want to use what the AI and I create together, I have to be part of building it.

I want to invite you to start paying attention to how you feel about the AI outputs in your life. Do you believe in them enough to share them or act on them? That reaction, whatever it is, tells you something.

Hit reply and let me know what you notice.


Save 25% on Life in Perspective at Barnes & Noble This Week

Barnes & Noble is running a pre-order sale, and my upcoming book Life in Perspective is part of it.

If you're a B&N Rewards or Premium member, you'll get 25% off when you pre-order before June 26. Premium members get an extra 10% on top of that. This is one of the few times B&N discounts pre-orders, so it's worth taking advantage of.

The book comes out November 3. It's about doing a real annual life review. Not just goal-setting, but looking back at what happened, what it meant, and what you want going forward.

Use the code PREORDER25 at checkout if the discount doesn't apply automatically.


Available Nov. 3, 2026

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