I have a basic distrust of OS updates. My coworker Joe used to religiously update his Windows box, and it died several times. I never used to update mine and it just kept marching along.
Now, I know that's bad, I need to do the updates for security and so on. So I am better about doing it on my PC and Mac. As for my Linux box, one time I asked our sys admin Tony if I should install the updates, but he said no. Then recently, he noticed I had over 100 pending updates, and said I should update. I pointed out that he had recommended against that earlier, but he couldn't remember any reason he would have said that.
After updating, my network connection no longer worked. Tony suddenly remembered why he had told me not to update. He worked some magic and I was connected again.
That was only a couple of weeks ago. I forgot about the bad part of that updating, so yesterday when I noticed some pending updates, I let it go ahead and update. Even after I lost my network connection, I couldn't remember from two weeks ago that the updates had caused that, so I had to call Tony over again.
This time I watched what he did, and when I twittered about it, Jeffrey Fredrick suggested that blogging about things that you might forget is a good idea. So next time I let my Linux box do updates, and can't connect to the network anymore, I'll remember to su root, go to /root/l1-linux-v184.108.40.206, and make install. This is only needed for kernel updates. Note to self!
I'm trying to get organized in other ways too. Janet Gregory has her own personal storyboard, just stickynotes on the wall next to her desk. I've adopted this at work, it really helps. I'm going to do it at home, too, I'm thinking about using the microwave door for it!