"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 in 2007, 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."

Cole wrote this song with Patrick Leonard, who also produced the track. Leonard is best known for his work with Madonna; he co-wrote and produced "Live To Tell" and "Who's That Girl."