Alwaysbehind referred me to this thread.
I want to tell you about my experience which is going on RIGHT NOW, about working with a trainer and gaining confidence. :)
I adopted a rescue horse in January who had BIG TIME issues with a lot of things, including gear (bits, saddles, etc.) I worked with a saddle fitter. I did ground work with him from Jan to about June and finally rode him in the round pen a few times. After that I was forced to move him to a boarding stable, so I took it all very slowly. We were doing great, and the fitter came out for one last look to make sure everything was fine. BOOM, bucking bronco. It was totally unexpected and the first time he ever acted even remotely dangerous.
You can bet it scared the bejeezus out of me. At the advice of the lovely ladies of this forum I hired a trainer. I was 100% honest about my fear issues. I have been working with her for weeks and we've come a LONG way. I was honestly too afraid to even get on him for a few weeks. My trainer rode him...so yeah. :) Now we're doing a lot of trot work, inside and outside, bending, etc. I took him on a trial 'walk' this weekend, where I led him with two other horses that were being ridden. I think he would have been fine if I would have ridden.
PM me if you want to pick my brain or anything.
I think it was the best thing I could have done for me AND my horse. :)
I hope to be on the trail by the end of fall or next spring.