I happened to do a whole bunch of reading on digital asset management this week, conveniently while I was dealing with my own digital asset mess. I was in the process of reorganizing my disorganized files so everything on my desktop was the same as my laptop (the digital version of cleaning my room & office). In the process my desktop ended up breaking down. Luckily everything was double backed up... but not the most organized back up. Files were all over the place and it made it extremely difficult and time consuming to locate what I needed. The worst was dealing with the Lightroom catalogs. I had several catalogs, relocating all the files and combining the catalogs took even more time away I could have spent working. I ended up loosing my whole weekend to fixing and reorganizing my computers and the files on them and I'm still not finished.
Moral of the story: If I didn't wait and had organized my digital assets organized a week earlier I wouldn't have lost a whole weekend of my life to the digital file management catch-up... Don't wait to the last minute like I did. A lesson I won't forget.