@dshanske I just helped my parents with their office (decades of stuff in there!), and used to be a professional organizer. Set up boxes/bags ahead of your organizing time and label them with one phrase that is either an action or a noun, so when you look at each container you know exactly what it is, and what to do with it. (e.g. "give away," "memorabilia"). Good generic ones are "to keep," "to give away," "goes to another room/place," and of course a trash bag. Figure out specifically the space you are going to work on -- to stay motivated for a big project, it is VERY important to see a visible difference when you are done. (Pick an area of a room, for example, and then specify THIS bookshelf, THAT cupboard.) Organizing is hard because it is all about making decisions, often about things with emotional contexts, so treat it like the difficult cognitive task it is, by setting a timer. I think 30 minutes is good, no more than an hour. Set up your bags/boxes ahead of time, set the timer and sort, sort, sort. Keep focused and you will make tremendous progress in much less time than you think. When the timer goes off you are DONE for that work session. Stop right there, and get the donations and trash out of the apartment, and put away things that belong elsewhere, where they need to go. If you manage your work sessions like this it will help you stay motivated. You can make an amazing amount of progress if you stay consistent about using the timer and setting the boxes up ahead of time. Hope this helps, and good luck. fwiw the more you get rid of, the less you have to organize.