I know things like the Jargon File exist, but I'm having fun writing this.
There is a gif from Malcolm in the Middle that's been floating around the internet for years that explains Yak Shaving better than I ever could.
It's basically when you need a series of often trivial things before you can do your main goal. The way it was explained to me was:
Your friend asks you to restore a WordPress site onto their server, it should take 5 minutes to do so you say sure.
- You want to restore WordPress from a backup
- but to do that you need to update their PHP
- but to do that you need to fix a broken dependency on an old PHP package
- but to do that you need a library that has to be compiled from source
- but to do that you need to install a GCC
- but to do that you need to fix an issue with their apt-get
- but to do that you need to schedule a reboot
- but to do that you need to ...
- ...
- ...
- but to do that you need to hike to the top of a Tibetan mountain and shave the hair off a Yak.