I recently attended a photography workshop in Yosemite. For an icebreaker for the workshop, we had to share our 10 favorite photos for the group. I had never ranked my photos so this was somewhat of a daunting task. However, it turned out to a valuable exercise that I recommend you try.
The process I followed was to use the star ranking system in Lightroom. For the initial pass I set aside 4 hours on a Saturday night. I went through all of my processed photos from the past 4 years and marked the ones I liked the best with a single star. I also found several photos that I like the composition but felt they could be improved now that my post processing skills have improved. I marked these photos with a purple flag in Lightroom so that I could more easily find them to work on them in the future.
I ended up with about 50 photos marked with one star. Knowing that I had to get down to 10 photos, I reviewed the 50 one star photos and tagged my favorites from that group with two stars and quit for the night. This reduced the number of photos to around 20. Several days later, I reviewed the two star photos and selected the photos with the best back stories as I figured that I would need to share the stories with the group. I marked these photos with the group.
I found this exercise valuable for a couple of reasons. In fact, I think that this type of review could become an annual event.
I now have a portfolio of my top photos for several purposes. For example: blogs, business cards, submission in photo contests, sharing with friends and potential clients.
I was able to identify photos that I liked but thought I could improve since my post processing skills have improved.
To see more of my photography, visit my website.