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In late 2015, O'Connell was named to the Out100 honoring LGBTQ icons. O'Connell was assured with Parsons and Spiewak he felt he could not trust a network with the gay content, fearing that they would let the project die after buying the option. In April 2015, Jim Parsons, who had read O'Connell's Thought Catalog article, optioned the book through his company That's Wonderful Productions which he runs with husband Todd Spiewak. Just as his second season with Awkward wrapped in 2015, his memoir I'm Special: And Other Lies We Tell Ourselves was published. While writing the book, he moved to Los Angeles and at 27, started his television writing career with MTV's Awkward. He later expanded the article into his book, which he publicly revealed his disability. In 2015, he wrote a column for Thought Catalog called "Coming Out of the Disabled Closet" about hiding his disability with the car accident. At the time, he kept his disability private. Some of his writing went viral and when he was 25, he was offered a book deal from Simon & Schuster.
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He contributed to Vice, BuzzFeed, and other publications including The New York Times and Medium. O'Connell worked as a blogger for three years, first serving as editor of Thought Catalog in 2011. Additionally, disabled representation in popular culture was nearly non-existent.
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He described feeling in limbo about his CP, not really fitting in with disabled or non-disabled people. There, peers assumed his limp was from the car accident, and he chose not to correct them. Nine months later, he moved to New York City to attend The New School. The accident resulted in compartment syndrome, and affected mainly his left hand. When O'Connell was 20, he was hit by a car and required four hand surgeries. His family was supportive when he did his sister, uncle, and grandfather had already identified as LGBTQ. He remained closeted until he was 17 and felt he needed to come out, to pursue another boy who was already out. I remember seeing Ryan Phillippe's ass and being like, "That's the most beautiful thing I've ever seen in my life." And then being, like, "Oh, fuck me: I'm gay and disabled this is so rude." The moment I realized I was gay was-truly- Ryan Phillippe's ass in Cruel Intentions. On discovering his sexuality, O'Connell said, He attended Foothill Technology High School. Later on he suppressed this desire, seeing himself not represented in popular culture. He loved performing as well, acting in all the middle-school and high-school plays. He would watch shows and attempt to figure out the A-Plot versus the B-plot, and the structure of the script.
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Growing up, O'Connell requested TV scripts for Christmas, and watched shows with the closed captioning on to learn more about writing. Because of his CP, he had ten or eleven surgeries as a child, spending time in the hospital, and received much physical therapy. He has a mild form of cerebral palsy (CP) since birth, which affects the right side of his body with a noticeable limp. O'Connell grew up in Ventura County, California with what he described as his " liberal" family.