Damilola is co-author of Life's Chrysalis, where he wrote “Rejection: Like Earth to Rain”. His writing has appeared in The Naked Convos, Africa on the Blog, The Guardian News Nigeria, Viva-Naija News, and Tuck Magazine. He also volunteers with PDBY News at the University of Pretoria. Damilola is an IREBS for African Real Estate Research Scholar at the University of Pretoria, where he is a Doctoral Candidate. He is the Head of Media and Strategy at Upside Africa. Damilola won the Biopage essay contest in 2018. He plays the saxophone for leisure.