....I'm also passionate about art. It is one of the few things that I do naturally and don't have to struggle with!!! Every other career path pretty much requires my having to modify how I feel or behave. But art is natural.
I also haven't been properly employed for almost 6 years now. The last three were spent trying to get back into the work force only to be fired twice. -this was very disheartening for me.
I remember doing a project with other long term unemployed people also interested in the arts -it was for a community art gallery and was one of the few periods in my twenties during which I greatly enjoyed my self.
Far from these individuals being 'losers' or 'hopeless' I actually found them to be highly interesting personalities. So, I hardly see how they are 'losers'. Probably, in fact, they were actually too interesting to fit in with the average person. One was a poet who hadn't been employed for 15 to 20 years and who had a great personality and was witty and charismatic. Another was an aspiring writer, who somehow had gotten very low marks in her final school year and yet who I couldn't help noticing to in fact be very bright. She was also a lot more alive than most people are.
So, perhaps one of the first things to do is to take care of your self image and your self esteem. -Don't allow yourself to pigeon hole yourself into fitting into some stereotype: the world will do this enough. And, if anything, it is more than likely to be the thing that you planned perhaps subconsciously to get away from. So, don't tarry in labels and in limited views of who people.
The other suggestion is to get involved in some sort of volunteer effort and preferably one that supports marginalised members of society -the misfits. you would probably bring more understanding to such people and have an intuition for how to treat them and see them.
Furthermore, volunteer work could lead you into a job. It would certainly help you in terms of 'work history'.
Another tip (that I am using) is to write on your resume that you have been painting and traveling. That you have sold your work and been commissioned to do portraits. ...unfortunately, for me this is a fairly big exaggeration. As I haven't done much art either -I've been too preoccupied with my emotional issues...
Anyhow, volunteer work is great. It will help you broaden your mind as to what you are capable of.