[1]: 3:00 In an interview with internet podcast called Midnight Express, Woodruff said that after college, she met some employees of TSR while attending a games convention in 1992, which led to the idea of a career as a freelance fantasy writer; subsequently she sent some material to TSR and one of her monster designs appeared in the Advanced Dungeons & Dragons adventure Assault on Raven's Ruin,[1]: 4:00 while her adventure A Way with Words, co-authored with Tim Beach, appeared in Dungeon magazine in its May/June 1993 issue.
[2]: 7:55 While there, she wrote World of Darkness: Gypsies and contributed to White Wolf's Vampire: the Masquerade, Werewolf: the Apocalypse, Mage: the Ascension and Wraith: the Oblivion lines.
[2]: 8:00 Woodruff was part of the design team on a multitude of projects including BattleTech, Netrunner, Magic: The Gathering (7th edition), Duel Masters, Dreamblade, and Pokémon Trading Card Game.
Woodruff was on the design team with Wolfgang Baur and Mike Selinker for a role-playing game based on Magic: The Gathering, but Wizards cancelled this project in 1996.
[8][2]: 31:15 While working at Lone Shark, Woodruff continued to freelance, interviewing participants and producers of various reality shows such The Amazing Race and Survivor, then publishing articles for now defunct RealityNewsOnline.