I find a lot of the concepts needed on here are really tough until you’ve come across them at least once.
Never enumerated a web-server for dirs before? You might not even know it’s possible. Never checked for file extensions in those dirs? Again, as others blow through and declare it easy BAU, you’re still scratching your head.
Same goes for the first time you have to enumerate DNS in anger, interact with SAMBA shares, or muck about with file upload bypasses.
Until you’ve done it once, you maybe wouldn’t even know to try it, let alone how to do it well! Once you’ve done most things a few times, you can look at a box and go “ah yeah okay, I reckon this is gonna need this tool from my mental toolbox”, and get moving a lot quicker.
I’ve learnt so much since I first started on here, but I still find each new box a struggle as there’s always some new trick to learn! 