That depends entirely on what's on the device I'm updating.
My phone has basically no important information and the entire thing is backed up in 3 different locations. I only update it when I absolutely have to because being without it if it bricks during the update is a nightmare, and most updates change the way the phone works and just end up irritating me. I don't know anyone personally that's ever had their phone remotely hacked, and even if they did... so what?
My work computer? It gets updated every night. There's a team of people that handle that.
My home computer? Well, MSFT is involved... that used to auto-update until they came out with that "upgrade to windows 10!" notification. Now I don't trust their updater at all and updates are turned off permanently. I'll update when I need to.
Linux installs stable updates on its own. Never had a problem.
Websites and things? Again, depends on the content. I've got a Teamspeak server that's been running on an EC2 Instance for years and I'm never updating that.