A graduate of Centre College in Danville, Kentucky, Strickland began his career as an intern photojournalist and feature photo hunter at the Advocate-Messenger in Danville. He worked for several years as a freelance photographer in East Tennessee before completing a 6-month internship with the Chattanooga Times Free Press. He previously worked as a staff photographer for the Texarkana Gazette in Texarkana, Texas, before rejoining the Times Free Press staff in February of 2013. He is among four Times Free Press staffers who were finalists for a Pulitzer Prize for the 2013 story "Speak No Evil" which explored the no-snitch culture in violent crime in Chattanooga, and he has received awards from the Associated Press Managing Editors' Association, the National Press Photographer's Association, and the East Tennessee Society of Professional Journalists.