You make a great point… The purveyors of the term “side hustle” are probably intentionally drawing on the connotations to imply there’s something illegal or unconventional about the enterprise. It’s making it seem like you “cracked the code” and it’s not in fact too good to be true… It’s “cures they don’t want you to know about,” MLM, “life hacks,” ect… The question is whether you’re bold enough to go out and take it!
What I find most obnoxious is how this pitch is now often deployed in the “sharing” economy of uber and the like… Rent a WeWork space for your side hustle or whatever. The pitch that somehow you’re an entrepreneur and not just another cog inside a giant mechanical turk. As they say, chances are you’re the mark.
This is the connotation that it calls to mind for me (see Midnight Cowboy)… or any kind of enterprise that is nontraditional or black or grey-market, and mostly sales-oriented (not money in exchange for labor)… It’s definitely a term glamorized by gangster movies and music. What’s weird to me is it’s gradual adoption to describe conventional white-collar work… But I guess that shouldn’t surprise me for the reasons @jerwin points out.
