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My curriculum files just get bigger each year. I have a folder for each story that is in our series and each year I add another idea. I also have a set of folders in my desk that I keep up with notes on each child. I toss those each year. After the first week I school I still have not got to that drawer yet. Haha!
Yes, at the end of every school year, I clean out my files. I do it again at the start of the year because there always seems to be more more stuff I won't need. I hate clutter! Plus it makes it easy to keep what I do have organized.
I clean out/hand off student files, but I rarely clean out my files of "administration" type stuff. I have, so far, cleaned out my subject area folders (like social studies units, etc.) every few years since I've started.