Courtney C.W. Guerra has been writing her Dear Businesslady column since 2014, first on The Toast and now on the financial advice site The Billfold. Starting out with experience in food service, retail, and data entryplus a joint BA in English and visual artsshe proceeded to build her resume through a series of administrative positions, both corporate and nonprofit. Shes spent most of her career as a writer and editor supporting humanities research at the University of Chicago.