388: Decluttering that Extra Difficult Spot or Category of Stuff

We all have (at least) one category of stuff that's extra hard to declutter. I'm addressing that today, inspired by this email: 

I am a teacher who, due to life circumstances, is leaving the profession shortly before I could be considered early retired. I am working part-time as a substitute teacher because I can not seem to let go entirely. My question for you is: how do I let go of all the teaching resources I have accumulated and created over the last twenty-plus years? As a substitute teacher, I would realistically only need some of the materials, but not 80 boxes worth. How did you deal with the process of letting go of your professional materials?

I have been stuck with this issue for a long time. I have other clutter issues, but at the moment, the professional materials are one area I would like to conquer soon.

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