Sometimes .... usually I just hit a wall because I don't know enough but I know enough to get myself in trouble .... so I just stop, reformat, reinstall and start all over.
About the biggest lesson I've learned from Linux is not to mess with too many things unless you want to learn about it and have lots of time in your hands.
Otherwise if you find a good distro for your needs, a stick with it, don't change it, update and backup regularly.