Originally Posted by Cherie
You will never gain the confidence to ride outside on unknown trails if you only ride in an arena on a push-button old school horse.
Althought that is ultimately true, it's still the place to start. You don't learn to swim by being thrown in the ocean. When I learned to scuba dive, it was in the pool at the Y under a controlled environment, not in 70' of water off St Thomas - but that is the reason I learned.
Just find the right instructor for the job you want to do and have the right tools for the job.