She attended Whitney M. Young Magnet High School in Chicago, then the University of Illinois at Urbana-Champaign, studying psychology.
[5] In 2016, The New York Times reported that Ajayi had an audience of approximately 500,000 between her personal Twitter feed and the Awesomely Luvvie website.
[6] Ajayi published her first book, I'm Judging You: The Do-Better Manual, with Henry Holt & Co in September 2016; it debuted at number five on the New York Times best-seller list.
"[4] Shonda Rhimes and Betsy Beers have acquired I'm Judging You to adapt as a cable comedy series through their company Shondaland and ABC Signature.
[8] In 2016, Ajayi was the first writer invited to speak at the National Museum of African American History and Culture, and her event sold out.