For the first 40 years of her life, Jennifer Finney Boylan lived as a man named James. Since her transition, Jenny has become an activist for the LGBT community through her writing and her work as the national co-director of GLAAD. In 2003, Jenny's memoir She's Not There
became the first best-selling work by a transgender American.
In this exclusive Oprah: Where Are They Now?
update, Jenny says she's seen remarkable changes in the culture, thanks in part to the media and entertainment industries. In May 2014, actress Laverne Cox, a leader in the transgender movement, appeared on the cover of Time
magazine. Then, in January 2015, Jeffrey Tambor won a Golden Globe for his role as a transgender woman on Transparent
. "We've seen trans people in the public eye, not because they're trans, but because they are going about the business of living their lives and working their jobs and raising their children like anybody else," Jenny says. "That's all big progress."
While Jenny says she's reluctant to comment on Bruce Jenner's case specifically, she does offer advice to public figures who plan to transition. "I would say, don't do a television show until your transition is complete," Jenny says. "Because you don't know where this journey is going to lead you, and doing your transition in a very public way, as I did, means that, to some degree, you come out as a transsexual woman rather than coming out as a woman."
Jenny says that if she could have lived a life that hadn't complicated the lives of the people she loved quite so much, she would have. "But, in the end, there was no choice. Coming out as transgender was never a choice," she says. "It was less of a decision than an erosion. It was something that simply had to be because I had tried every other way of being happy."
Watch the above video to find out how life as a woman has given Jenny a sense of peace.
More from Oprah: Where Are They Now?