When it comes to side hustles, the best way to make money and have fun is to find a side hustle that you really love. I’ve tried well over 100 side hustles over the years, and landed upon a half dozen that I truly enjoy. These are the gigs where I make regular, consistent money ($1,000+ per year), like freelance writing, selling used clothing online (it’s a bit of a love-hate thing), blogging, and playing cash app games.