I just wanna to give you guys a little update. I've been riding outside the ring almost every time i've ridden lately and I think I've gotten a little more confident with it! I even took shaggy over a small cross rail and he did great. The best part was the canter! Because there was no small corners of a too small ring to bind us, I was able to canter him some and not feel scared! (I don't know how many of you know about my cantering issues. Long story short I fell off first time I cantered him and ex trainer never worked with me or let me canter a different horse so I lost all my confidence at the canter.) Granted I might I have posted some but I did try to sit back as much as possible. There was one little moment where I was circling him on the flat and Idk if I gave him the signal or not but he cantered and I was able to sit it for a few strides! Either way it was one of my most successful rides!