After graduating, he drove a New York City taxi for nine years, during which time he wrote two stage plays, a novel, twenty screenplays and various other works.
Schaeffer rose to fame with fellow actor/writer/director Donal Lardner Ward on the independent film My Life's in Turnaround (1993), which was made in fifteen days for only $200,000.
He signed on as a client of Creative Artists Agency and made a deal to direct the 1996 romantic comedy If Lucy Fell for a budget of $3.5 million for Columbia TriStar.
In recent years Schaeffer has been writing an autobiographical blog, I Can't Believe I'm Still Single, about his relationships and ongoing search for love.
The series, which was about people who failed at suicide – originally titled Failure to Fly – starred Schaeffer along with Krysten Ritter, Ivan Sergei, Ving Rhames and Rachel Hunter.