I've had my first horse of my own a year next month and I've been afraid to ride alone. I did it once or twice and fought him trying to get back to the barn and got thrown off once when something spooked him. However, he (Peanut) and I have come a long way with each other. He is a very experienced horse who's had multiple owners and I am a first time horse owner who at the time was afraid and lacked confidence. Not saying I'm an expert now by any stretch, but I feel like Peanut and I have built on our relationship and understanding of one another and I have learned alot about control and paying attention to the signs a horse gives as to what he's about to do.
With that said, I have been thinking alot the past two days since I got my new trailer about taking him somewhere away from the farm and giving it a try. I have been relying on someone else to go ride with me and as everyone else said, when you wait on someone else there's no telling how long you'll wait.