Stein's career began as a writer and researcher for "Martha Stewart Living". He worked a year for Stewart and later quipped that she had fired him twice in the same day. Stein did fact-checking at various publications before becoming a sports editor and columnist for "Time Out New York", where he stayed for two years. While working at "Time Out New York", he was a contestant on MTV's short-lived game show "Idiot Savants". Stein joined "Time" in August 1997 and his last column for the magazine appeared on November 16, 2017. In signing off, he began, "Since my first column, 19 years ago, readers and co-workers have clamored to have me fired." He concluded, "There are times when society needs a punk who doesn’t care. There are far fewer times when society needs a 46-year-old punk who doesn’t care. I’ve always been guilty of hanging on too long out of fear of graduating college, ending relationships and transitioning from democracy to authoritarianism. I look forward to a future columnist who makes me laugh about that."