This has been true with my workflow lately, too. I had to switch to a loaner computer while mine is being repaired. The loaner has a much smaller hard drive, so I had to move things to an external drive. I've done that a few times in the past and things are a big mess. So I'm using this opportunity to try to clean things up, including my bookmarks.
The problem is that it's a huge job and I don't really have time to sit down for the hours it would take to do the whole thing all at once. Also, boring. So I've been doing it in chunks, making sure it is clear where I left off. Very moderate.
Now I just have to apply this to the rest of my life, particularly the part where it's easy to maintain. I tend to get stuck feeling like if I don't get all the way organized then there's just no point, when for me that isn't true at all.
I organized a bunch of files at work this fall. Now I can't remember the system I used. It was even color coded! The colors are still there, but the meaning is lost. I think this time I will paste the key on the front of the filing cabinet. And no, you may NOT come visit me and laugh.