I used to do this, until I ran into the problem of an update breaking some critical piece of my workflow the morning right before I had some important work to c

I used to do this, until I ran into the problem of an update breaking some critical piece of my workflow the morning right before I had some important work to complete. It's not a good look when you have to ask your co-workers to wait for you because you have to stop and fix your computer first. (Although these days software is so unreliable that maybe no one bats an eye anymore? Who knows.) Since then, I've learned that it's not a matter of IF an upgrade will break your system, it's a matter of WHEN. There will always be that one bug that slips under the radar and breaks something, and it's usually right when you can afford it the least. These days, I do approximately weekly upgrades of all my systems/gear, but I make sure to schedule it when I know I will have the time to fix whatever issues come up. (In an enterprise setting, the expanded version of this is called Change Management.)