Hustler. That word catches a bad wrap for some reason.
Around my junior year I stopped asking my mom for lunch money and of course this caught her attention. She asked me if I was eating and if I was doing something shady for money. I told her that I had been cutting hair in the football locker rooms and she replied "Ok! Glad to see you found your hustle". You see, high school was a little different for me, I went to a predominantly white school; those of which came from wealthy families ( I don't come from a wealthy family). My mom worked hard but with two kids on her own wasn't easy, we were living poor amongst wealth, so naturally you need to adapt. That's Jamaica, the people here don't have time to muddle around or complain, you must adapt.
So to me a hustler has never had any negative connotations attached to it. I see a hustler as someone who takes what is given and makes the best of it no matter how much or how little.