There must be a rare personality type that never experiences this kind of overconfidence. Perhaps a less glamorous cousin to the Buddhist beginner's mind?
There are certain classes of autistic people who are very good at always following the rules and finding people who are not. And in certain places they are exactly what you want.
I find that if I am doing something "dangerous" (example might be using power tools) I have to say to my self "be careful this is dangerous" to avoid being on autopilot and making casual errors. Maybe a better example is the way you train yourself after you've picked up a box the wrong way and pull something to try to remember each and every time to watch your specific movements.
But at some point, you will become complacent, and it will taken a mistake to remind yourself again.
We've all done it. I shut down an NT4 production server because I was connected via remote desktop and clicked shutdown rather than log off. This was back in the day when there was no pop-up asking for reason you want to shut down and confirmation.
AFAIK that edition had logoff instead of shutdown on the Start menu for that reason. You can still access shutdown by hitting Ctrl-Alt-Del on the console or clicking Windows NT Security.
I have to remind myself this every time I start up Sequel Pro now since in the last release they switched the command keys for Run Selected... and Run All...