Trans author Jenny Boylan is no stranger to the public spotlight. Her 2003 memoir, She's Not There, was the first bestselling work by a transgender American, she's a nationally known activist for civil rights, she's the national co-chair of GLAAD and she has shared her personal transition story many times on national television, including on a 2005 episode of "The Oprah Winfrey Show."
Since her own transition nearly 15 years ago, Boylan has been happy to see what she calls "remarkable" changes in the culture, thanks in part to the visibility and universal acclaim of shows such as "Transparent" and trans celebrities such as Laverne Cox, of "Orange is the New Black."
"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," Boylan says in the above video from "Oprah: Where Are They Now -- Extra."
Boylan first shared these thoughts in the midst of the wild media speculation regarding Bruce Jenner's gender identity, before Jenner sat down with Diane Sawyer for a much-anticipated interview in which he came out as transgender. While Boylan was reluctant to comment on Jenner's case specifically, she did offer advice to public figures who plan to transition.
"I would say: Don't do a television show until your transition is complete, because you don't know where this journey is going to lead you," she says. "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.
"I want people to accept trans people in all their messy complexity, but there's a lot to be said for knowing when to be public and when to be private," she continues.
Still, Boyan understands firsthand the burden of living a life that feels untrue to who you are.
"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 tried every other way of being happy."
Now that she has been presenting as a woman for more than a decade, Boyland is also acutely aware of how it feels to be able to live her truth.
"The big surprise to me was that life as a woman was so fulfilling," she says. "I guess it shouldn't have been a surprise, but it was a surprise that when all was said and done, I found not just a sense of peace inside, but also a sense of connection to the rest of the world."
"Oprah: Where Are They Now -- Extra" is a web-based spinoff of the OWN show "Oprah: Where Are They Now?", which airs Saturdays at 9 p.m. ET.
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