I have spent my years half-assing my photo organization. I place my photo projects in folders with subfolders of working files, web-ready files and the RAW camera photographs. The system in theory works for the longterm as folder-based structure hasn't changed in a few years across multiple operating systems. If keep maintaining the system, keyword my images, and update my metadata, things should be alright correct? Yeah right!
I've got problems galore. Some of my files have consistent naming structures and a few have some keywords but not all the proper ones to find an image. I truly have a mess on my hands. I own a copy of Lightroom, have Aperture and use Photo Mechanic. All of these tools are great yet I don't use them properly. It is time to put effort into cataloging my files.
Digital photography creates a ton of visual diarrhea free of the limitation of film. I've been going through my images as far as 2004 and haven't found many that I like. I see no need to keep most of them. If all of my hard drives crashed, I would feel a great sense of loss and would lose some precious images (I love my cloudscapes!). I'm still alive today and every day is an opportunity to take new, better photographs. I recommend to stop looking at the past for gems–look ahead my friends! The past is for reflection and nothing else.
Keep the images that you have a good reaction to. Delete photos that are junk with ruthless abandon! A friend's insight sunk in my head. I understand the whole thing about seeing your mistakes and using them as a reference/learning tool, that hard drive space is dirt-cheap or key-wording speeds up searching methods. A big house doesn't need every square inch filled with furniture. Empty spaces can be a great thing.
I show very few people my contact sheet. I don't want someone to have to go through my junk to figure out what I consider gold. I certainly don't want to, life permitting, go through my photos as an old man lost in a pile of digital clutter. I have thousands of images and maybe one hundred I'm proud of showing. I might be wasting my time cataloguing but with a good system in place, I won't even have to think about doing this in the future...unless file-management changes in the next decade.