First off, I want to congratulate wilsonbro on being the first poster I recall seeing use the
smiley naturally and in context. Congrats!
Second, I want to mention, in case you are not aware of, the example of Ted Hawkins. Hawkins spent years busking on the Venice boardwalk, playing his guitar and singing for donations. Against the odds, he was "discovered" and got a recording contract, resulting in an amazing soul/blues album:
The fact that he was old by the time this happened, and that he died not too long afterwards, is neither here nor there.