Originally Posted by SyntaxPC
At some point I tried it standing up again, however, I tried putting most of my weight over the handlebars. That's when it "clicked" for me. I think it might have had something to do with getting some of the weight off of my feet and off of the rear wheel.
That's weird, I had the opposite happen to me. When I first learned, I was leaning most of my weight over the handlebars because I read somewhere that you should have your center of gravity over the front wheel. I could do about 5 second trackstands that way, but my wrists would start hurting. When I eased off the handlebars and put my weight on my legs and the cranks, it "clicked" (more like some voice going "yaaaaay" in my head) and felt more natural since I was standing on my feet. I could hold the trackstand longer if I shift my weight to my legs instead of my hands.