Heh, you want to try busking for a no boundries experience. I did that for a couple years back in my early 20's. Started out one day as a way to get some beer money, but the money was so good I kept at it for a couple of years.

(Until the money grubbing "Busker Festival" started coming to town and ruined it for all. Then, on top of the aggressive panhandling that came with that turning everybody off, the property owners started seeing the dollar signs and wanted to start charging for locations... Everything changed just like that. There had been a certain 'troubador nobility' to it all, but it went from a few 'keepers of the faith', with respect and comraderie to competition and begging from any idiot with 4 strings still left on his guitar... Anyway...)

For me at least, it was and still is harder to play for more intimate settings. I think even during my busking experiences, there was still that expectation of performer/audience. Once that's gone, it's very personal and harder to put myself out there.

I played some bars from time to time and even a couple of competitions and those situations were similar. Whether somebody is watching me or I'm just background for their conversation, there was a "place" for everybody; an expectation. The more intimate the situation, the less that exists.