Likely began as a freelancer or through contributions to existing game projects. Precise details of her initial projects are scarce but can be inferred from her distinct design style that would be developed later.

_The Shab-al-Hiri Roach_, a unique and highly influential role-playing game, was published. The game, known for its surreal humor, philosophical themes, and innovative mechanics, quickly gained a cult following within the indie RPG community. It was credited to R. Borgstrom.

During this period, Jenna likely continued to support _The Shab-al-Hiri Roach_ through supplemental materials, online discussions, and engagement with the fan community. The game's popularity and distinctive style helped establish her reputation as an innovative game designer.