Prep School Transgender

Summer 2014

By Alexandra Scott

Over the past several years, transgender issues in schools have increasingly appeared in the mainstream press. Coverage ranges from the challenges to the triumphs — from the struggles of individual children and families trying to get support at school to the student health plans at Harvard, Brown, and Duke covering the cost of sexual reassignment surgery. We have come a long way, but still have a long way to go.

One of the clearest memories of my career comes from the early 1990s when I was teaching at an independent school in the Boston area. This was the early days of the Gay, Lesbian, and Straight Teachers Network (GLSTN) — now the Gay, Lesbian & Straight Education Network (GLSEN). A very popular teacher at my school decided to come out of the closet. Students and faculty rallied around him with teach-ins and workshops about the harm of covert and overt homophobia. Students came out of the closet soon after. Then some parents became alarmed. Petitions started circulating calling for an end to the movement. Was school a place to be concerned with sexual preference?

The head of school responded by asking the student/faculty gay and lesbian support group to put on its anti-homophobia presentation for the parent community. The performance began at 7:00 p.m. on a school night. As parents filed in, I could see rigidity and a readiness to argue in the eyes of many. When the group finished its presentation, the school head slowly stood up. Everyone anticipated that he would open the floor to comments or questions. Instead, he boomed in his deepest baritone: “I could not have said it better myself.” The anger and discord in the room completely deflated. Contentious parents filed out silently. Supportive parents and students celebrated. In this pivotal moment, the school culture experienced an important seismic shift. Of the 40-plus parents who signed the petition, three withdrew their children and sent them to a very traditional boarding school. The rest of us went back to class.

I know that other schools experienced a similar cultural shift around the same time. But sadly, the shift has never felt complete. To this day, there is a level of resistance in the independent school community to fully embracing and supporting LGBT students and faculty. A few weeks ago, I met a school head who, in response to a question about whether his school has an LGBT alliance, told me the following story. “I was at a Southern school head’s conference. At the morning cracker-barrel session, three headmasters lamented turning down students who wanted gay alliances at their schools. The heads professed to believe that LGBT students are entitled to a school-sponsored club, but were unable to approve the club because of the potential parental uproar. They seemed sad about not giving approval, but were unwilling to fight the battle.”

As a former head of school and current consultant, I have fought those battles. They quickly become mean-spirited and divisive and sometimes negatively impact the school’s pocketbook. They also can put the head in professional jeopardy because most boards prize institutional peace. Getting along with neighbors tends to trump acting in the best interest of children when acting in the best interest of students challenges some parents’ beliefs.

For me, this is both professional and personal. While the call to be a woman had been hanging around in my consciousness for years, I ignored it for a long time — perhaps because being transgendered is still considered socially aberrant or perhaps because I kept myself very busy and never allowed myself to come to terms with those feelings. For a period of time, I thought I would be happy being metrosexual, with the perfect clothes and grooming. Then I threw myself into being the best dad possible. Now that my children have left the nest and seem to be happy and self-confident, I finally had no more distractions. No more excuses.

Throughout my life, the urge to transform would both scream and whisper. As I dove into a psychoanalytic mindset, I examined and reexamined whether my interest in being a woman was related to psychological complexities. Did I want to be a woman because I was raised in a matriarchy? Because I had been “hormonally washed”? Because I was reacting against a very distant, alcoholic father?

In a quiet period in my life, I turned to an even more intensive meditation and yoga practice. The nagging notion that I am called to be a woman kept reappearing. At first I struggled with the question of form. What difference does it make whether I appear to be a man or a woman? Isn’t the content of my character what matters, not how I look? I tried to let it go, but I couldn’t. While I was proud of my work in schools, I was never able to appreciate myself. While I had a number of interesting head of school positions, I never felt satisfied. For my own health, it was clearly time to act.

Over the past year, while holed up in a bungalow in Florida, I have written and am preparing to publish a book on my experiences. A few months ago, I started the required counseling in anticipation of transitioning genders. Some weeks ago, I began the requisite hormone regimen.

One bright, warm, sunny Florida Sunday morning, I decided to try out a church. While I am a divinity school graduate, I have eschewed church for the last 30-plus years — for both doctrinal and political reasons. But I knew that it was time to leave my burrow and make friends. Where better to do that than at church?

Dressed in a stylish but unassuming Anthropologie dress, I took a deep breath and entered the sanctuary. I did my research beforehand and went to an “open and affirming” church. In addition, I had privately met ahead of time with the head minister to do a community suitability pulse check. The church greeters were effusively welcoming and asked me if I wanted to be introduced to the congregation. One deep breath later, I said yes. Everyone there was warm and inviting.

Later, I spoke with the minister. After the usual post-sermon congratulations on a homily well done, we spoke of my form versus formlessness dilemma. We talked of the central importance of the incarnation, of God bridging the gap between human and divine in the personhood of Jesus. Good point. The body does matter — a major epiphany. I am forging ahead with my transition to womanhood and, in my case, wholeness.

But, of course, in the world we currently live in, my wholeness comes with complications and frustrations.

Over the past several months, I’ve increased my job search and sent out a number of cover letters applying for school positions, many for which I am “overqualified.” Each letter contained, in addition to my interest in the position and essential qualifications, the following sentence: “Finally, in all fairness, I think it important to point out that I am transgendered.”

To date, I have had two Skype interviews, multiple no responses, and a few auto-responses. Neither of the Skype interviews translated into an actual interview. One resulted in an abrupt email: “The committee has decided to move forward with another candidate.” The other drew a classic cheerful-dismissive response: “Though you are not a finalist, I have to tell you that our Skype interview was incredibly compelling…. Alex, if there is anything I can do to help you in your search, I would sincerely like to help!”

I understand the nature of employment law and why and how circumspect school leaders have become in articulating the rationale behind employment decisions. I have also watched as independent schools have become increasingly risk averse and pander to the expectations and prejudices of powerful and outspoken parents.

I “know” the reason I have not been invited to interview for any of the jobs I applied for: the risk of negative reaction is too great. As the aforementioned Southern heads demonstrated, all it takes is one very loud parent willing to rally the community to make a school head duck and backtrack — even if it means pushing aside the school’s diversity and mission statements. Besides, there are a lot of wonderful candidates out there. Why pick the one who could be a hassle?

Independent schools have developed comprehensive diversity programs, welcomed gay teachers and students, and increased economic and racial diversity. It’s been an important and historic transformation for the community. But the work is incomplete. Now is the time for independent schools to dig deeper — to not just consider the rights of LGBT students, faculty, and administrators, but to embrace and support them. As Scott E. Page of the University of Michigan notes in his recent book, The Difference: How the Power of Diversity Creates Better Groups, Firms, Schools, and Societies, our cultural strength literally lies in our diversity.

In particular, the community needs to take a long look at the “T” in the LGBT community. Are schools willing to sensitize their community to transgender issues? Will school heads hire qualified transgendered teachers and administrators? Will transgender students be comfortable coming out of the closet and safely assume their place in school? Are schools ready to handle the challenges of athletics and gender identity? Have they considered how they’ll educate parents about transgender issues? Will boards hire qualified transgendered people to lead their schools?

The answers to these questions are both complex and simple. Creating and nurturing school cultures that focus on encouraging students and teachers to maximize their potentials seems simple. But in the context of a larger culture that appears to be led by people who grow more and more narcissistic and mean-spirited every day, this task will require courage, mindfulness, and a relentless attention to detail. Being intentional about replacing the eye rolling and cutting remarks with unconditional support and consistent acts of kindness will be a Herculean task fraught with opportunities for criticism.

It’s not easy. I get it. But it can — and should be — done. I once saw a head of school call daily for “random acts of kindness.” While sighs of resignation and snickers at the repeated request ebbed and flowed, the school did become a kinder place. Students and faculty began to reflect the “random acts” mantra. Community service grew. Inclusion became a conscious process in relationships. Being thoughtful became cool.

I have a dream that independent schools will lead the way in making the culture a safe and happy place for all people. I can envision the day when schools will offer expansive personal growth workshops, model intentional change, and collectively create truly safe places where all people can not only be authentic but also thoughtfully collaborate on maximizing potential. The world is shifting dramatically. Our problems are legion — overpopulation, growing poverty, environmental devastation, political polarization, dramatically changing job markets. Change is a fact of life. Adaptability, flexibility, and learning to work together are crucial for a healthy present and future. The place to start is in schools. The way to start is by teaching mindfulness and learning to accept and nurture each other for who we are and who we want to become.

Alexandra Scott

Alexandra Scott is a former head of school, teacher, counselor, and coach. She can be reached at www.alexscottconsulting.com.