A former print journalist, Leif was a staff writer at The Dallas Morning News from 2001 to 2003, and also contributed to Newsweek, the San Diego Union-Tribune and D Magazine in Dallas. As an undergraduate at the University of Southern California, he was named one of the top ten college journalists in the United States, and won second place in the prestigious Heart National Writing Championship. He was named National High School Journalist of the Year in 1997 by Journalism Education Association.