In 1989, Lippert helped to establish Outright Vermont, an organization dedicated to serving the needs of lesbian, gay, bisexual, and transgender youth.

[2] Later, he was involved in lobbying for Vermont's gay civil rights bill, which passed the legislature and was signed into law by Governor Howard Dean in 1992.

[2] For twenty years prior to serving in the Vermont legislature, Lippert worked in community mental health services, serving as a psychotherapist and substance abuse counselor, and for ten years as the Executive Director of the Counseling Service of Addison County.

In 1996, Lippert resigned as CSAC Executive Director to continue his legislative career and grow the Samara Foundation of Vermont.

The seat had been held by Democrat Chuck Ross, who resigned on being appointed U.S. Sen. Patrick Leahy's state director.

In the year 2000, as the vice chair of the House Judiciary Committee, and as the General Assembly's only openly gay member, Lippert was central to the work of drafting and passing into law the landmark Vermont civil union law which granted legal recognition to same gender couples.

Following passage of the civil union law, the Vermont Democratic Party faced a backlash and lost its majority in the House.

Subsequently, Lippert lost his position as vice chair of the Judiciary Committee, though he easily won re-election to his seat in the House.

Work on this bill had been postponed in 2000 following the December, 1999 VT Supreme Court's Baker v. State decision, which unexpectedly sent the debate for same-sex marriage to the Vermont legislature for resolution.

Lippert has also notably advocated for "Driving Under the Influence" to be set at a blood alcohol content of 0.05%, roughly two drinks within one hour for a 150-pound person.

[4] On May 12, 2007, Lippert received national attention when a Fox News crew, on behalf of the program The O'Reilly Factor, interrupted his breakfast in the Vermont statehouse cafeteria to demand why he had supported transgender rights but did not support Jessica's Law, for which host Bill O'Reilly is an advocate.