I recently moved my photography work from Flickr to a page on my own website and in the process, selected a much smaller set of images. I used to have about 150 photos on my Flickr account, all of them uploaded at a time when I deemed them good and then never touched again. I never went through that list and sorted out the ones I really no longer liked because I thought it was a good thing to have a lot of work to show.
When I decided to move my collection over to my personal site I first planned to take along the entire thing but then thought "Who will ever actually page through hundreds of mostly mediocre photographs?" – I certainly wouldn't.
I decided on a much smaller set, around twenty, but quickly faced a problem where I wasn't able to remove enough from my Flickr collection to get down to that number. I just felt too invested in these pictures since I remember where and when I took each of them, how much work went into them and how great I thought they were at the time.
Instead of filtering the "bad ones" out, I went with the same approach that I use for throwing out things that I own: I clear out a shelf, drawer or whatever and then put things back, starting with the most important ones and asking my self "Do I really want to have this?" for each item. If I would do this with my kitchen utensils for example, the first things to stay would be my big kitchen knife that I use for just about everything, my best cutting board and the heavy frying pan. I imagine it much like being at a store and having to pay for all that stuff again, not really of course but it helps to get into the right mindset. Another thing I sometimes do to keep clutter under control is to get rid of one thing when another thing is added.
So, I did the same with my photographs. I started picking the very best ones and when I got to twenty, each one I wanted to put in the collection had to be "traded" for one that was already in. It turned out to work really well. I now have a portfolio that I'm actually proud of. Before, I often felt the need to say things like "Oh, that one, yes, I took that long ago. I would do it better now", even if I'd just say that to myself. Not anymore.
After that there was still the issue of that big pile of images that were still sitting in my Lightroom catalog, most of them never finished, never shown to anyone and most of them not actually good. I also had tons of almost-duplicates. Several exposures of essentially the same shot, kept around in case I'd "get back to that sometime", which I never actually did, of course.
I used the same approach again: Put all the ones I really needed or wanted to keep into named folders, made sure there are no duplicates and then dumped the rest also clearing all the flags, star-ratings and color labels that had accumulated over the years.
When I was done, I had gone from over 2000 photos taken over seven years down to 384. That's still much more than I had decided to put out publicly but I think it's a necessary amount to still see how my photography changed over the years.
It's quite liberating and refreshing. I now have a much clearer picture of what I did and what part of it was actually any good instead of just having a pile of stuff that's just good enough to think "Yeah, I've done a lot, that's cool". Having a much smaller collection also sets a higher bar for the future. I'm less tempted to keep images around that aren't better or at least different than the ones I took five years ago.