1. When we struggled for month with using OpenSSL, fixing our server, then bit of Sqlite3 fuck ups. Was it even right to use those libs, not write shit ourselves, if it is such a hassle to use them, or is it only us being too stupid to read the docs? Project seemed 'finished' for over a year. Really wore us out to get it out there.
2 Our board constantly announcing the success and striving of our pentester department. Makes me feel I am at the wrong place. No dynamics, growth, just too much stupid work to plow through.
3 Starting a bit with CTF's. Realizing I am hardly at the entrance of the rabbit hole. (And also is it even the right thing going down there? My Luddite tendencies also shining through...) Not mastering all this tools.