Jeff was glad to assume the role — but Jess had qualms. Unbeknownst to the town officials and constituents when Herbst was appointed, Herbst was already in the process of transitioning. She started in 2004, when Google introduced her to cross-dressers.com, where for the first time in her life she got to chat with people who questioned their gender. Then, she found a group on Meetup called Dallas Feminine Expression. It took her a full two years to work up the courage to go out in public as Jess, but once she did, Dallas Feminine Expression gave her an actual in-person community of trans friends. Soon she was an organizer of the group, hosting regular girls’ nights at Sue’s, a lesbian bar in Dallas’ “Gayborhood.” Over time, she came out to her daughters, and to most of her friends and all of her consulting clients. Her days as Jeff dwindled as she spent more and more time getting to know herself as Jess. And in 2015, with Debbie’s blessing, she started hormone replacement therapy.