Girlboss culture is now, as they say, cringe, but during the 2010s, SO MANY of us thought we were on the precipice of busting through that glass ceiling. We thought we could rise and grind, hustle our way to the life of our dreams, and as long as we loved what we did we wouldn’t work a day in our lives. Leigh Stein is also a recovering girlboss, who went into debt building an organization that supported women but left her burned all the way out.