The Trouble with Trashing

Recently, my dear roommate's dear sister moved into our house from another state. She brought almost nothing with her. Glancing into her newly set up room for the first time, I felt envious of the openness. Though my tiny room was clean it felt crowded. I associated this feeling with messiness. "I have too much stuff," I said to myself in my head. To ditch the thought that I was somehow failing as an adult for keeping everything that has ever been sentamental to me, I decided to trash some of my things.
The trouble with trashing is, it goes against almost all of my values to just throw things away...How do I solve this problem? Clothes are easy; they can be given away, or used as fabric. What about the dead pens, broken jewelry, fake flowers I have used in 3 or so costumes (and now look dead)? What about the warn-out hand bags, shoes, tiny broken boxes? I sit, and stare, and feel guilty. Get discourage, stop cleaing...try again tomorrow. I shuffle, I give some away, I use items as blocks trying to turn them into something useful. I research: disposing responsibly, DIY blogs. I draw, starring.
The trouble with trashing is, it isn't simple.