First, fear is real. And since horses can pick up on our fears and build on it, I think it is best to take things in small steps. Part of that was my time flying jets in the military...the goal is to push the envelope, not leave it. There was a WSO I met when I was a young Lt, who had been in a crash landing. He survived, the pilot did not. After he healed, he tried to return to flying, and managed to conceal things for quite a while - until one of the other WSOs noticed him vomiting (we lined up before take-off, and you could see folks in the cockpit of the plane next to you). Turned out he still had nightmares, and was vomiting before every flight. He gave up flying, but no one thought him a coward for doing so.
But with horses or people, sometimes we need 'sacking out' - pushing things far enough to make us uncomfortable, but not so far that we panic. And that means taking small steps, and thinking in advance on how to stay safe wile doing something that has significant risk involved.
I've never been afraid of trail riding, but when I rode Mia off property last week a few times, it was the first time in 3 years. I wasn't afraid of riding trails, but of riding HER on a trail - and the experienced riders I know who know her agreed that made sense. She was - and to a lesser extent still is - a spooky, nervous horse with plenty of power and endurance who can bolt mindlessly when afraid.
Being 'afraid' of that is not cowardly, but smart. After not riding her at all and spending nearly a year of working hard on MY riding skills, I hired a trainer to "re-break" her - and the trainer concluded she knew so little that she had probably never been broken at all. In that sense, my spooky mare was an uncommonly well--mannered horse...and now she was 11 and entering training.
The training has been wonderful for her.
A big part of that training has been me walking her by herself on a lead line out into the neighborhood. At first, we couldn't go more than 100 yards without her getting visibly nervous. Over time, we've built up to walking out into a patch of nearby desert - but I still haven't taken her out by herself when the wind is blowing hard.
This gives the horse a chance to get used to things, but it also gives the person a chance to build a relation with the horse, and to find out how the horse responds. For example, while walking her, I found that I can back her up when she gets nervous - back her up 100 yards even - and she will remain focus and in control of herself. But if I turn her, she panics. Folks have told me to disengage the horse if it gets nervous, but disengaging means turning, and turning panics Mia. What works 20 times better with Mia is to either stop, or, if she is already getting scared, back her up until she isn't so scared. Then stop, scratch her neck, and then encourage her to take a few steps forward. I cannot 'work her' past a scary thing without making it more scary. I have to 'calm her' past the thing.
My first ride out on her was with the trainer riding the gelding she shares a corral with, and the trainer's job was to keep an eye on both of us. Reminding me to BREATH. She recommends that if you feel nervous on a horse, take a deep, audible breath in, slow count for 2-3 seconds, then audibly breath out. She says (and I'm pretty sure she is right) that will relax your body and calm your horse even if you still FEEL tense.
When I ride my BLM mustang pony out by himself into the desert, I use an English jump saddle. With Mia, I won't ride her in an arena unless I'm using an Aussie-style saddle, or a western one (I prefer Aussie).
I have ridden horses in my cowboy hat, but I won't mount Mia without a helmet. I also wear long sleeves riding her. If that makes me a coward, so be it. Taking precautions can help ease fears, and it certainly can help minimize the damage if things go wrong.
I'm hoping to ride Mia out on the street today without the trainer. But I'll keep an eye on her. If she gets nervous, we'll back up. If I think things are building up inside her, we'll turn around - 180, then walk. We won't disengage, and we won't push it. I'll ride her on property for 15-30 minutes first. If she is having a fussy day, we won't head down the road.
Not just for my sake. It has taken nearly 4 months of hard work to get her to this point. If I take it slow and build her confidence, then someday she'll be a confident trail horse as well as one I can ride in an arena. If I push her too far too fast, she'll break and we'll be back at the beginning.
What is true of horses is also true of people. You want to "push the envelope", not leave it...and all of us have envelopes!
Pushing the Envelope *|* Independentflightinstructors.com 
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