Every time (by which I mean 2 times so far) I update docker something stops working in one of my containers. Is this common or just my incompetence?

You should be more stable than that if you're not using experimental features.

But there's a lot of known unknowns on your query:

Are you using docker, or docker for mac/windows?

Are you updating your operating system at the same time?

Are you using fedora/CentOS/RHEL? There were recent changes to default permissions and groups that were breaking

Have you taken the time to configure rootless docker?

It's docker on mac. There was no change whatsoever on anything, just docker. I enabled some feature in the settings and it worked again. No clue why that fixed it either.
I should probably finish that docker course I was doing.