I've never been a "real" sysadmin, but back in the mid 80s I learned that anything you don't practice doing regularly will inevitably be painful.
I was working as a developer at Unisys (or it might have still been Burroughs), down the hall from the OS developers (for one of Burroughs' 3 distinct mainframe product lines, each with its own cpu architecture, operating system, system software, etc.). At that time, our mainframes could be patched while running, without re-booting; re-booting was considerably slower than patching. As a result, as each new OS patch was developed, it was applied on the fly to the machines in our dev environment, and they hadn't been rebooted for something like six months. It turned out that it was possible to have a sequence of patches, which when applied on the fly to a running system caused no problems, except that when it came time to reboot, it would crash. You can imagine the fun of trying to debug which change (or combination of several changes), out of many months of development work, had broken the boot process! These dev machines were shared with other teams (compiler developers, database engine developers, etc.), so the productivity hit waiting for our dev machines to be available again was substantial. After that, the policy was that the OS developers took turns coming in early one morning a week to reboot the dev machines, so in the worst case they'd only have to track down which of the last week's worth of patches might have broken the boot process.