No matter how small the mistake, if you made it, the cat is out of the bag and you're screwed. No matter whether you notice and correct it - in light of the current spying climate, you can be certain that your mistake was logged somewhere.
There's so many things to keep in mind in order to avoid mistakes, I can't even imagine them all.
Misconfigured your browser to not use tor when posting? Sending the bitcoins donated to you to somebody who gets compromised later? Disconnecting from tor without first logging out of StatCounter and then checking your stats? Plugging your USB-stick into a machine infected with some BIOS malware?
The possibilities are endless and you don't get even a single "extra life" (to use a gaming term). Screw up only once and you're screwed forever.
It's kinda like software security: It has to be perfect. Even if it's mostly perfect and only one single vulnerability exists and is known, you're as screwed as if your software was open like a sieve.
The days of anonymity on the internet are over. Yes, you can build sufficiently high hurdles to guard against most people, but those that really want to know, will know in time.