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The Roaring Twenties

Artwork by Freda Chiu

quarter life crisis. when the world should be your oyster, but is really your Inferno.

—Ripped Ranger, 3 November 2009 | Urban Dictionary

I was scheduled to board a flight to New York with my boyfriend in twelve hours. Halfway through packing, I sat myself down on the couch and began crying. I wasn’t sure why; everything about the trip was going to plan. Earlier in the year, I’d enrolled in an improvisation course at the Upright Citizens Brigade training centre in Manhattan as part of a professional development grant I’d received. I’d spent the previous year studying at The Second City in Chicago (an institution renowned for churning out comedy superstars such as Tina Fey, Amy Poehler and Stephen Colbert), trying to retrace the footsteps of my idols, which eventually led me to New York and the UCB.

“You’ll love New York,” sang a chorus of well-wi...