Not only is Issa Rae the insanely talented star of HBO's Insecure, but she's also the writer, producer, and creator of the series, which means one of the first thoughts that probably crosses your mind is: teach me your ways. So we did exactly that, as Issa joined us at this year's POPSUGAR Play/Ground to share her most valuable and inspiring words of wisdom, as she talked of overcoming self-doubt and breaking barriers.
After she opened up about her rise to the top, we sat down with the star to get to know her even better with a game of firsts — where she revealed everything from her first splurge . . .
. . . to the story behind her very first audition.
Check out the full video above to watch it all go down!