When did your project management tool become another thing to manage?

I’ve been thinking about this a lot while building Bracket.

We have tools to manage almost everything now, but somehow keeping those tools updated has become work of its own.

You finish a meeting → update the project.
Client changes something → update the project.
Decision happens on Slack → update the project.
Deadline moves → update the project again.

And if nobody does it, everyone slowly starts working with a different version of what’s true.

That realization changed the way we’re building Bracket.

Instead of asking “how can we make project management easier?”, we started asking:

“Why should people have to manage the project management tool at all?”

Would love to know if others have felt this too.