Hi - welcome to Susan's. I understand your fear of rejection - it is a real gut punch and end even if it has nothing to do with you being trans it can really undermine your sense of self worth and confidence.
I've recently been reemployed after a four month stint out of a job, I would consider that I have a lot of confidence but even so that four months was not great and I got pretty depressed in April. I live in a reasonably accepting city and was applying to fairly open minded organisations and I don't believe the fact I was passed over in interviews had anything to do with me being trans - even so it started to play on my mind a bit. I found that I was more open, confident and connected in interviews presenting as female than I ever was when I was pretending to be a dude - I think it just boiled down to the fact that there were better candidates than me.
Problem is if you decide to not try because of a fear of rejection then you may miss out on an awesome job and a good work experience. Working for yourself can yield great results if you have the passion and drive and (usually) money behind you but it is often a very difficult enterprise - who will do the work for you when you are sick or need to take a break for example, who will do your finances, etc. But if you are talented in a certain area then focus on that as a potential avenue for revenue - just don't expect it to support you straight off the block, you may want to consider a part time job regardless. If you never try you'll never know.
