I'm kind of awesome at organizing. This caused another problem. The collection of stuff that I (used to) have was a little depressing. Once you understand the principle of letting things go, your life seems to be a little less... heavy. I don't know why I seemed to enjoy collecting things. Maybe it was my past trips to the store with family. There was always a certain emotional bond tied to shopping.
You really discover how much you truly have when you're preparing to move. Since high school, I have moved five times. You would think that after that many moves, I would have pared down to just the essentials by now. Not true, unfortunately. With every bag of stuff that would come in the door, you just kind of make room for it!
This all changed once I was finally on my own. I say "on my own", because there was always some bit of financial help that I was receiving from my parents until I was around 21. Once their money stopped flowing, I tended to clutch my hard-earned dollars much more aggressively. I shake my head now at others (like myself) who take the financial help for granted, but I understand it's something that must be experienced.
I had this realization that no, I didn't need a pair of $40 jeans. And why do I own 80 shirts? I only really wear about 20. Why did I think I needed to go spend money that I didn't have on things I didn't need? I can blame my childhood or anything else, but I realized that some people never truly understand that they don't really need all of this.
I guess what I am getting at is that it's important to dig down deep and figure out why you think you "need" all of the stuff you think you need. Can the shirt that you've worn once be useful and cherished by someone else? What about that pair of jeans that you're keeping on hand in case you lose those last 10 lbs.? My advice: give anything you don't find useful now away. And don't look back.