
In the spring of 2015, the landscape for the transgender community was irrevocably altered by a single, seismic event: Caitlyn Jenner’s interview with Diane Sawyer. I remember it vividly, not just as a viewer, but as someone in the room, having served as an advisor to Diane Sawyer, her 20/20 production team, and the ABC executives. We knew we were creating something that had the potential to be a watershed moment—a high-profile, sensitive, and deeply personal portrayal of one transwoman’s journey to her authentic self. For me, and for so many others, it was a profoundly validating experience. It was the first time that a person of such immense public stature had so vulnerably shared a story that, in its essence, mirrored our own—minus the Olympic medals, of course.
The interview was a masterclass in humanizing a community that had long been relegated to the margins of public discourse. It was a moment of hope, a powerful narrative that transcended the tabloid frenzy and spoke to the universal human desire to live an honest life. We hoped it would open hearts and minds, proving that our struggle was not a choice or a curiosity, but a fundamental part of the human condition.
But in the decade since, much has happened. Caitlyn Jenner’s political journey has diverged sharply from that of the trans community she once helped illuminate. She has embraced conservative politics, aligning herself with a party that has actively championed the very laws and policies that threaten the rights of trans people across the country. Her public statements have at times been viewed as dismissive of the struggles of a community facing relentless attacks on everything from healthcare access to the right to simply exist in public spaces. The woman who once told the world, “I am a woman,” now often seems to live in a political world that seeks to deny that truth to others.
And so, the question that haunts me today is not a political one, but a deeply personal one: I wonder what Caitlyn Jenner is thinking these days? Her immense wealth and celebrity undoubtedly afford her a level of protection that most trans people can only dream of. Does her privilege shield her from the daily assault? Does she have to worry about which state’s bathroom she can safely use, or if her family will lose their health insurance because of a new anti-trans law? Does she, like so many of us, feel the knot in her stomach every time a new bill is proposed, wondering what aspect of our lives will be legislated away next?
In spite of her political affiliations, Caitlyn Jenner is still a member of our community. She carries the knowledge of our shared struggle, the pain of being unseen, and the courage it takes to live authentically. As the attacks on our right to exist escalate, I can only hope that, on some level, she worries too. I hope that the immense vulnerability she showed in 2015 is still a part of who she is, and that it allows her to feel the weight of what is happening to her trans siblings.
For all the division, the core truth of that watershed moment remains: we are all human, we are all seeking our authentic selves, and no amount of privilege can ever fully erase the shared reality of what it means to be transgender in a world that is still learning to, or simply would rather not, see us.
With Transgender Day of Visibility here once again, I find myself thinking a lot about the word vulnerability. At one of my most recent speaking engagements I challenged the audience with this question, “What is your relationship with vulnerability?” I’m willing to bet that for many of you reading this, that is something that you rarely think about – because why would you in the first place? You may find yourself in the fortunate position of being gainfully employed, with a roof over your head and food in the cupboard. So why would a concept like vulnerability ever enter your stream of consciousness? The simple answers to these questions are that you wouldn’t – probably never. And judging by the collective “Hmmmm” sound the audience made I doubt they had too.
The exact opposite, however, is true for far too many transgender people who choose to be visible in our society. By being visible as their authentic selves they risk being vilified by those who choose hate and fear over knowledge and allyship. And for transwomen of color, this can be particularly dangerous, leading to being victims of violence at alarming levels. Everywhere we turn it seems as though there is another anti-trans bill being rushed through conservative-led statehouses that seek nothing more than to eradicate the existence of transgender people of all ages.
But what choice is there? To remain silent and shuttered away never to be seen in public is simply not an option. Yes, we are different – and if you stop long enough to listen to the stories of our journeys to our authentic selves, trust me, you’ll be moved because they are powerful beyond measure.
But there’s another side to vulnerability that I’d like to bring to your attention. As we begin to change the narrative that seeks to position my entire community as a political wedge issue it is vitally important that we have ever-increasing numbers of allies by our side, standing in solidarity with our quest for equality and inclusion. And at the very core of allyship is education. I have learned over 17 years of talks and trainings that for learning to truly happen, one must allow themselves to be vulnerable. To say to yourself, or out loud, “I don’t know everything, but I’m willing to learn.” It is at that precise moment that the heart, the mind, and the soul open and allows teaching to take hold.
By being intentional about learning and allowing that experience to fuel our allyship is how we begin to move the needle on equality and inclusion for transgender individuals of all stripes and all ages. It can be a truly transformative experience – if you let it. And that’s something to consider not just on the Transgender Day of Visibility, but every day of the year.
