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What's one thing you automated that ended up making your business more complicated?

I've been thinking about this a lot lately.

Automation is supposed to save time.

But sometimes you automate one thing, then need another tool to monitor it. Then another step to handle failures. Then notifications, backups, and manual checks just to make sure everything is still working.

At some point, the "automated" workflow starts needing its own maintenance.

I ran into this while building automation for my digital product workflow.

The original goal was simple: remove repetitive work.

But the more steps I connected, the more things I had to keep an eye on.

It made me realize that automation isn't always about removing work completely.

Sometimes the real goal is just choosing which is worth automating and which work is better left simple.

Curious if anyone else has run into this.

What's one thing you automated that actually made your business more complicated?

on August 23, 2026