Not only is Issa Rae [1] the insanely talented star of HBO's Insecure [2], 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 [3] to share her most valuable and inspiring words of wisdom, as she talked of overcoming self-doubt and breaking barriers [4].

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!