If you're a creative freelancer using AI and still not making more money, you're not imagining it — the math in fact doesn't work out the way everyone promises. This episode is the honest, unfiltered version of that problem, starting from a night I couldn't sleep doing that exact math in my head.

I'd been lying awake doing math in my head, realizing I was repeating the exact same overcommitting pattern I swore off in 2025 - saying yes to clients randomly, never actually productizing my own service even though I tell other creative professionals to do it constantly. And the math got worse from there: with everything AI has supposedly changed about how I work, I'm charging roughly the same as I was before any of it.

This one's for my editors, designers, writers, video people, social media managers - anyone whose work sits a step or two away from a client's actual revenue, which makes "just charge more" a lot harder to pull off than the advice makes it sound.

I get into why the work itself slowly gets worse when AI lets you take on more than you can actually hold, what I've started doing differently (including capping my client roster and bundling deliverables instead of taking on more people), and the harder question underneath all of it - whether the real fix is productizing, upskilling into something closer to the money, or stepping away from production work entirely.

I don't wrap this one up with a bow. But if you've had your own version of the 2am loop, I think you'll feel it here.

If this one hit home, hit subscribe on Apple Podcasts or Spotify so the next episode lands in your feed automatically.

The written version of this plus a couple of things that didn't make it into the recording — is up on my newsletter and Substack.

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