go for it as long as they stop! the sheltland i used to ride had no breaks, so when i galloped him out bareback i could only turn him and he would eventually stop. i also use to gallop out my 14h pony that absolutely loved to gallop. he was dead easy to stop though.i took him over a 2ft log out and did it better then in the feild :) i still ride out now and then bareback on my mare that can be scatty. i find it easier to stay on her bareback sometimes rather then with a saddle on :) i'm like you, i prefer hacking then schooling.