Schaeffer graduated with a degree in drama and dance from Bard College, in Annandale-on-Hudson, New York. After graduating, he drove a NYC cab for 9 years, during which time he wrote two stageplays, a novel, 20 screenplays and various other works. He rose to fame with fellow actor/writer/director Donal Lardner Ward on the 1993 independent film, My Life's in Turnaround, which was made in 15 days for only USD200,000. Schaeffer and Ward parlayed Turnaround's success into Too Something, a short-lived television series that was briefly renamed "New York Daze." He signed on as a client of Creative Artists Agency and made a deal to direct, If Lucy Fell, for .5 million at Columbia TriStar, for which he was taken to task for casting the model Elle Macpherson as his love interest. In 1997, he starred opposite model Amanda de Cadenet in Fall, about a cab driver who picks up a model and takes her back to his apartment, where they begin a passionate affair. In 2000, he released Wirey Spindell, a semi-autobiographical tale. Never Again, starring Jill Clayburgh and Jeffrey Tambor, came next and was followed most recently by 2004's Mind the Gap.