I started my faction warfare career with minimal solo PVP experience. I had previously tried to roam solo, but there was always the fear in my mind that I would loose, and always did. I never fly anything I can't replace, so it wasn't the fear of all of my ISK tied into a ship. I think it was just the fear of failure and looking inept. I didn't think about whether or not the pilot in the other ship was feeling the same, I just assumed that they were better than me. Having done a lot more solo in the last two months, I've come to realize that this isn't always the case.
In my effort to conquer the fear, I started taking advantage of the free ships Fweddit offers. What better way to learn than on someone else's money? The problem with this was that they weren't always available in a timely fashion and you were at the mercy of what was available. None the less, it was enough to get me started plexing and making ISK while putting nothing at risk beyond my ride back to Egg in a pod.
Sitting in a plex, in my free thrasher, I was running the timer down when I saw a hostile decloak. I admit, I panicked at first as I saw the torpedoes streaking toward my ship. The white contrails standing brilliantly against the starry backdrop of Sifilar. My head cleared when I saw the pitiful amount of damage he was doing to me, and recalled my days of wannabe bomber pilot - torps do terrible damage against small ships. Filled with adrenaline, I pulsed my MWD to close the distance between us and unloaded my guns into her fragile Nemesis. I think I destroyed it in maybe three volleys. It was my first official solo kill in the books.
From that point on, the fear slowly started subsiding. I've since stopped relying on the free ships as much and started shipping down batches of my own ships down. I'm still inexperienced for the most part, but I'm slowly understanding the way things work in practice. You can read hundreds of battle reports, write-ups and blog posts, but none of them assuage the fear as much as actually doing it yourself.
Since that fight I've lost a bunch of Condors, my current ship of choice, without batting an eye. I've learned how to break some kity ships and leave intact, how to better guess what I'm going to be fighting against, and best of all I've learned to give a gf and chat about it with my opponent. All of the losses that I had been afraid of pale in comparison to the thrill of battle and the euphoria of winning.
I guess what it boils down to, as our saying goes, is YOLO.