Jan began writing and directing independent films in 1980, and by 1984 had completed an award-winning trilogy of films about working-class adolescents in Boston, Billy In The Lowlands, The Dark End Of The Street, and The Tender Age. The films starred John Savage and Kevin Bacon, as well as young men and women from the projects of Boston. In 1985 he directed the critically acclaimed mini-series for American Playhouse, Roanoak, one of the first dramas about Native Americans to use the Ojibwa language. In 1986, he adapted and directed Lanford Wilson's play Lemon Sky, starring Kevin Bacon and Kyra Sedgewick. which was awarded the Special Jury Prize at the Sundance Film Festival.

He then directed a series of television pilots and movies, including Gang Of Four, about four young high school students, and Against The Law, about a renegade Boston attorney, which became a series on the Fox Network starring Michael O'Keefe. In 1991 he directed Michael Caine in the feature film A Shock To The System, featuring Liz McGovern, Swoozie Kurtz and Peter Riegert. Jan then returned to American Playhouse and directed Big Time, starring Mia Sara, Dennis Boutsakaris and Adrian Pasdar. In 1993 and 1994 he directed Kane, a pilot for ABC; The Last Hit, for the USA Network; and Justice In A Small Town for NBC. In 1995, he directed Original Sins for CBS, and The Surrogate for ABC. In 1996, he directed The Elen Hart Peña Story for CBS and the Pilot for the series Orleans, starring Larry Hagman, which premiered in January of 1997. Jan has directed two long-form concert videos, Squibnocket, featuring James Taylor, and The Road To You, with Pat Metheny.