๐คฎ I hate gui config! Way too much hassle. Give me cli and a config file anyday! I love being able to just ssh into my server anytime from anywhere and fix, modify or install and setup something.
The key to not being overwhelmed is manageable deployment. Only setup one service at a time, get it working, safe and reliable before switching to actually using full time, then once certain it's solid, implement the next tool or deployment.
My servers have almost no breakages or issues. They run 24/7/365 and are solid and reliable. Only time anything breaks is either an update or new service deployment, but they are just user error by me and not the servers fault.
Although I don't work in IT so maybe the small bits of maintenance I actually do feel less to me?
I have 26 containers running, plus a fair few bare metal services. Plus I do a bit of software dev as a hobby.
I don't think the issue is listening to music, but installing potentially dodgy software that could bring a virus into the corporate network. Hence most businesses handling sensitive information try to protect their systems and networks by preventing unauthorised installation of software.