Abbi Jacobson Credit: Emmanuel Olunkwa

Abbi Jacobson, best known as co-creator and co-star of Broad City, did what some people wish they could do after a hard breakup: hit the road to distract herself from her pain. Only she was able to pitch her three-week solo road trip as a book titled I Might Regret This (Essays, Vulnerabilities and Other Stuff). She knows this is bizarre and privileged.

At a sold-out Chicago Humanities Festival event at the Vic Theatre moderated by author Samantha Irby, Jacobson recalled her decision to drive from New York to Los Angeles after wrapping season four of Broad City. Her work on the show was a huge distraction from the breakup but once filming and editing concluded, she’d be left to face her pain. Aside from getting away, though, Jacobson wanted to challenge herself to write in a longer essay format. “I’ve spent the last 10 years writing scripts,” she said. “Essays seemed like the next thing I wanted to do.”

Her writing process consisted of jotting down notes and lists and recording voice memos. The pencil drawings that accompanied her essays consisted of album covers or podcasts she listened to. Her decision to draw in pencil came from her desire to let readers feel like they were browsing through her personal journal or sketchbook, even if this meant they would point out imperfections in her grammar or the fact that she can’t draw hands.

Other highlights of the conversation included Jacobson’s art podcast A Piece of Work and her past relationship. This relationship was the first time she had ever dated a woman and the first time she had ever been in love. I Might Regret This, as funny and self-deprecating as it is, discusses the complexities of Jacobson’s sexuality, including how she never let herself explore the side of her that was attracted to women because she felt she had to be straight.