Henry Winker experienced first-hand the struggles of being a child with learning disabilities. In an interview with the National Center for Learning Disabilities Henry shared, "School was very difficult for me, and very painful. School and I were not made for each other. No one knew what a learning disability was back then, so everyone just said to me, 'Oh, you're funny, and you're verbal and you seem so smart, but you do so poorly in class. It must be that you're lazy.' And other people would say to me, 'No, you're just stupid.'"
Henry's learning disabilities weren't diagnosed until he was in his thirties. In school, Henry had trouble with reading, spelling, and math. Yet he went on to receive his B.A. degree from Emerson College where he majored in drama and studied child psychology and was awarded a Master of Fine Arts degree from the Yale School of Drama.