As far as feeling freedom in my career now versus five years ago... I think if I feel any more free it's simply because of the experiences that I've had, and the wisdom I've accumulated from that time.
In Irish law, busking is considered vagrancy - you can be arrested for it. It's risky asking people for money in public. So it's not like it's a high-art job. And people who do it as a high-art job make very little money.
If you believe in what you are doing, then let nothing hold you up in your work. Much of the best work of the world has been done against seeming impossibilities. The thing is to get the work done.