Congrats on your journey in getting rid of stuff. I'm on a similar quest myself, but I think your gusto has motivated me even more.
One quote of yours struck me though: "I feel like I’m holding on to old things just because I’m worried that I’ll lose my drive to make money.". I don't see what's important about making lots of money anyway? I recommend taking Steve Pavlina's advice and try to find your life purpose, separate from money. As long as you make enough to live and have enough saved in case you can't work any more, and are doing something you love in life, what more do you need than that?