This is my approach. End of the year is the great cull. Once I have trashed everything that I know I don't want, then I use Graphic Converter to rename and index originals in sequence. Typically MMDDYY_001 and up, GC grabs the date from the EXIF file.
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Hopefully it goes without saying that everything is redundantly backed up locally and statically, before I embark on the culling or editing process. A back up that auto updates is your worst enemy for this process.
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This is my problem really. Everything is either by date or in sequential order. So I have to try to remember when I took it.With our new Photo Association game, this is really biting me now -- the years during which I never bothered to caption/label/title an edited image or set up and use keywords and a DAM system. I do have my folders labeled now, even the old ones, so that at least I can open one up and hopefully find that image that I vaguely recall having shot lo these many moons ago, but it would have been so much simpler had I also titled the actual image file as well!
It has been only fairly recently than I've gotten my act together and properly labeled images as well as overall folders and I think it will pay off in the end. However, yes, at times it can be challenging, especially where there are several images of the same subject; in that case I have to either for example, use "glass vase 1," "glass vase 2", etc., or if it's a subject which is alive and moving and doing something I can use more specific titles such as "Alfred standing on pier," "Alfred Gazing into the Distance," "Alfred Headshot"...... Some abstract images are not so easy to define and in those cases I do resort to "Abstract 1," "Abstract 2".....
As a Lightroom user, you have a superb tool for keywording. People approach keywording differently. I have 9 keywords to define broad genre like nature or food, etc. Ratings and sorts by capture date get me the rest of the way there. I rate first, keyword only 4’s and above. It’s pretty simple.This is my problem really. Everything is either by date or in sequential order. So I have to try to remember when I took it.
I have a hard time trying to name photos and caption them. I maybe only caption a few of them. I know it makes them more visible I just find it tedious to do.
Zero. I have a folder structure only. Century/Decade/Year/Month/Date (when photo was taken)
Do you also keyword your images?