"14" was Paula Cole
's first single after a seven-and-a-half year break. After her second album, This Fire
, took off thanks to the hits "I Don't Want To Wait" and "Where Have All The Cowboys Gone?," her third album, Amen
(1999) was a letdown. With her record company in turmoil, Cole sat out the next dog year, taking time to raise her daughter. When he returned with the album Courage
, she had a lot on her mind. "I was frustrated and that's what came out," she told Songfacts regarding this song. "I was looking back at who I was at 14 and wanting to break out of molds."