By the time The Vampire Diaries ended, Paul Wesley was a staple of the show, and not just as the main good-guy love interest Stefan Salvatore. He began directing episodes in Season 5 and became a producer during Season 8. "I spent a year shadowing directors, attending meetings, prepping, sitting in the editing room, etc. Even though I have been working in TV for years, it ended up being such a blessing because I learned invaluable information," he told BuzzFeed. This experience behind the camera would prove useful as he started his own production company, Citizen Media, and began making deals of his own.

In 2019, Citizen Media partnered with Kapital Entertainment to produce Confessions of a Drug-Addicted High School Teacher and Possessed. "I've admired the work that Aaron and Kapital have been doing, and I'm very excited to team up with them to create content we can be proud of," Wesley, who's appeared in Tell Me a Story after starring on The Vampire Diaries, told Deadline. Wesley signed on to star in Confessions of a Drug-Addicted High School Teacher, so fans can watch a more experienced version of the actor they fell in love with.