Simon was left alone to care for his younger brother after the death of his father. Both he and Lucas have no memory of the fire that killed Frank, implying that they were not around when he died. After being orphaned, Simon and his younger brother moved to SimVille and rented a cheap apartment in the Lil' Apartments lot. He got a job in the teen education career in order to pay the rent and the bills.
Simon had few skills at the start, and had little experience with children, aside from walking his brother to and from school. However, his determination helped him succeed as an overachiever, having reached the top of the teen education career and maintaining a solid A+ in school. A chance card recently got him fired, however, plunging him and his younger brother into deep financial trouble as the family has no other source of income. Simon was devastated by this and allowed his grades to slip precariously.
Simon has a lifetime want to reach the top of the education career. He is passionate with children, hence his career choices. While Simon wasn't taught how to study before his father's death, he taught his brother this skill after the two were orphaned. Simon was later taught to study by Amar Newbie, despite the latter not being part of their household.