[4][5] Prior to making her first feature-length film, Drunktown's Finest, Freeland previously worked as a production assistant, as a writer and as a camera intern.
[6] Freeland worked for a number of different media companies, including The Food Network, Walt Disney, Comedy Central, and National Geographic.
The 95-minute-long film[9] is a coming-of-age story about the complex issues surrounding identity and the struggles faced by Native American people.
[9] Freeland, who is herself a transgender woman, also directed a digital series about queer and trans women called Her Story.
[12] The series was nominated for the newly created Emmy Award category of Outstanding Short Form Comedy or Drama.