It takes a few years to get to that point, that's for sure. And those local guys (no sleeper on the cab, eh?) are reckless sometimes. They do a ton of backing so their skills are excellent but they're always in a hurry because they normally go home when the work for the day is done. So the sooner you get finished, the sooner you get home.
Please, please for all new drivers - do not try to back in a hurry like that. Take it slow. I promise you - 90% of backing accidents happen because the driver doing the backing has someone waiting for them to finish so they get nervous and get in a hurry. Being a truck driver means from time to time you're going to hold people up. There's no way around that. Don't think about it for a moment. Focus on doing whatever you have to do to get that truck backed in safely. If people have to wait - too bad - cuz sometimes you're the one waiting on others so it all works out even in the end.
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This video is just amazing to me! Probably because I have never driven a truck before.
Video: Backing Into A Tight Dock
Truck driving backing up into a tight dock