When you're a junior sysadmin but still have to maintain ALL the production server:

How it looks:

$ sudo apt-get update

How it feels:

& sudo [ $[ $RANDOM % 6 ] == 0 ] && rm -rf / || echo *Click*

Russian Roulette eh? Lol

Just wait until you hit senior sys admin.

I follow the rule of it works don't update it until it starts nagging atleast I did until I was running Ubuntu 12.04 in 2017 haha

Maintain an almost exact replica. Check on it first. If it doesn't work, fix it so you know what you are doing. May not always work but it saves your ass and you have all the time in the world not bin to worry about the actual production being down.

I've a confession thus is a true story of 1 year ago now I'll feel a little more secure so far to say that now is RANDOM % 12 instead of 6

Hate to sound pedantic mate but this where investing time in learning a configuration management tool like Chef,Ansible or Puppet comes in handy. If this was 10 years ago I'd empathize but there's really no excuse today.

@binhex to me you're not pedantic and all those tools are in my list of things to learn but I simply don't have the time.