Recently, Madison Country Day School capped off homecoming week with a dance at the Overture Center. Students, whether straight, gay, transgender, cis, or nonbinary, all celebrated together to the beats of a popular local DJ. I’m so proud MCDS high schoolers accept each other as they are.

When I was a student, I felt unsafe in school. Always.

Facing Discrimination and Discouragement 

I never found school very engaging. In elementary school, I was an outsider. I knew I was different. As I got a bit older, I still had a hard time claiming my place in school. In high school, I was elected student body president. But the principal of my school said I could not take on the role: gay students were not allowed to hold the office. That harsh message could have left me defeated, but it ended up inspiring me instead. The experience motivated me to work harder and outperform those around me, making it more difficult for those in positions of power to discriminate against me because I was gay.

Many years later, when I finally got the chance to become a head of school, I made it one of my goals to make sure that every child feels included, feels known, and feels they belong at my school. I think about how much more I would have learned if I actually felt safe at school. I think of the ways I would have been involved as a student if I had felt I belonged. I want to work to make that change.

When I graduated from high school, the most popular college major in the United States was education. I wanted to be an education major, too. But my mother, the original tiger mom, said absolutely not. She told me that I’d never make any money in education, and somebody in our family had to make some money. It was straightforward. I could go to law school or medical school. Those were the two options.

As a head of school, I’ve prioritized increasing teacher pay. I don’t want others to be discouraged from a career in education because of money. Our son is a young teacher. I want him and everyone else who is called to the profession to be compensated for their talent, hard work, and commitment to their craft.

But at the time, I did what my mother told me to do: I became an attorney. I worked as a partner at a law firm and as the lead counsel for a major automobile company. All the while, I really wanted to be a teacher. So, when I found out that the auto company I worked for was planning to fund and start an alternative school, I jumped at the chance to help.

Catching a Break 

I did legal work to help establish the new school, but mostly I loved to be on campus with the students. They came there because traditional schools had not worked out for them. This school was their last stop—they’d never had a fair break. The school we built helped those kids blossom. Over time, I could see how different they were. I could see how going to school at a place where they belonged allowed them to open up to learning.

By contrast, working in corporate America did not allow me to live fully. I spent so much of my life closeted. At the time, an openly gay person was not going to be promoted to the positions I held. It was exhausting to never talk about my life.

Eventually, I left the auto company and took a job as the general counsel for a dotcom startup. We were a software company, and, in those days, school technology was just taking off. We got permission from the company to equip a school with technology. We set up a full computer lab and every other imaginable tech device. But the faculty at the school weren’t prepared to teach computer skills and put the tools we’d supplied to use. So, I volunteered to teach the technology class. And I just loved it.

The most amazing thing happened next: we sold the dotcom, and literally the same day—it was actually my birthday—a life-changing opportunity came to me, like a gift. I was at a concert with the head of school at my own son’s school, the school where I’d been teaching technology. Since trading had closed for the day, I told her we had sold the dotcom company. I wanted to celebrate! She said, “Great. Then you can come run my school because I’m leaving. I’m done.” She was retiring. The school had hired another person for her job, but at the last minute the new hire fell through. She told me the school really needed me. It might shut down if it didn’t have a leader.

I said, “What do I know about running a school?” It turned out I knew quite a lot—and I had a lot to learn.

Too Important to Fail 

That night, my partner and I talked and talked about whether I could help the school. This school was the most diverse independent school west of the Mississippi. He urged me that the school was too important an institution to allow it to fail. In the end, I agreed. I told the school, “You know what? I’ll do this for a year for you for a dollar.” Literally, that was the deal.

In due course, I took part in an educational leadership program for mid-career training at Teachers College at Columbia University, and off I went. I ended up working at the school for 11 years. The job was demanding, but I loved it.

I did face challenges along the way. Earlier, when my partner and I had enrolled our son at the school, we were the first gay couple ever admitted there. We did not receive the warmest reception. They had no history of gay parents at the school, and some faculty and parents were uncomfortable. Indeed, when I became the head of school, some families left.

But when I became a head of school, I decided I was not going to hide who I was. I realized that the kids—especially the ones who were gay or questioning their sexuality or gender identity—needed a role model. I wanted to show all the students that a gay person can be successful, can lead a school. At the same time, I wanted to show that being gay is just one component of who you are.

Later, I served as head of school at another school in West Hollywood. I ran a $100,000,000 capital campaign there. We knocked down the school and rebuilt it in four years. In 2020, the new school was completed, and I felt my work there was done. I planned to take a sabbatical. Soon, though, I realized my sabbatical, like so many other things, would be canceled by COVID.

Leading an Independent School 

I got a call about a school that needed a new head of school in Madison, Wisconsin—Madison Country Day School. Years earlier, when I was a lawyer, I had tried a case in Beaver Dam. I spent my weekends staying on the square in Madison. I fondly remembered enjoying the lake at the Union Terrace.

I learned that MCDS had an International Baccalaureate (IB) high school program and was working toward becoming a full continuum IB school. The IB program is recognized around the world as the gold standard in education, one that develops caring, inquisitive, self-motivated learners. That piqued my interest. One of the schools where I had worked had a history of enrolling the children of families employed by different countries’ embassies, and many of those students came to our school from IB programs. These students would arrive ready to go—they were curious learners, and they were globally minded. I wanted to take on the challenge of getting MCDS authorized as an IB school for all grade levels.

My immediate focus upon coming to MCDS was guiding the school through COVID. Since then, we’ve increased teacher salaries and benefits. I am grateful that the MCDS community has embraced increasing teacher pay, which has resulted in retaining and hiring the most talented educators. Thanks to those gifted educators, Madison Country Day School is now officially Wisconsin’s only independent pre-Kindergarten through grade twelve IB World School.

I’ve also worked on inclusion and belonging initiatives at MCDS, incorporating faculty and staff training with Welcoming Schools and GSAFE. Welcoming Schools, run by the Human Rights Campaign Foundation, helps educate school employees about how to create LGBTQ+ inclusive schools, how to support transgender and nonbinary students, how to prevent bullying, and how to welcome all families. We also focused on how to make our workplace more inclusive and welcoming for LGBTQ+ colleagues. GSAFE, a local organization dedicated to creating just schools for LGBTQ+ youth, taught us about meeting the needs of LGBTQ+ students. I want to open our adults’ eyes to what it feels like to walk these halls as an LGBTQ+ student.

We’ve been able to implement trainings like these because MCDS is an independent school. I’m an advocate for independent schools. Independent schools, by their nature, are able to do autonomously what’s best for the students in their care. The leaders at independent schools are able to make decisions based on what’s happening right there, on the ground, every day.

A Challenging Path to Happiness 

At school, I try to be authentically who I am. I want every member of the school community to be able to do the same. I’m mindful that there are people who may feel uneasy that I am running their child’s school. That’s the cold, hard reality. At the same time, all students are safe here and able to be open with who they are. The students are supportive of their classmates and comfortable with this. For the straight students, I’m glad that they see me, a gay person, in a leadership role at school.

Madison is a welcoming space for me, as was Los Angeles, where I worked previously. But not all educators in our country are as fortunate as I am to work in places where they are welcomed as they are. I’ve served on the boards of the California Association of Independent Schools (CAIS) and the National Association of Independent Schools (NAIS). Both of those organizations wrestled with member schools discriminating against gay faculty, staff, and students.

Given the current political climate, it’s challenging for young LGBTQ+ people to consider a career in education. In the last year, more rights have been taken away from LGBTQ+ people than in a very long time. It feels like your rights are slowly being eroded around you. And it’s really scary—especially for students.

But I’m in education for the long game. Life changes, and I’m hopeful about the future. So, I would encourage young LGBTQ+ people to pursue work in teaching or school administration. We also need people who’ve already begun their careers, for example, people with business experience or social work experience. Being an educator has been the most fulfilling work of my life. I’m so lucky to be able to help the kids and help the faculty and staff, the people who are making the magic happen in the classroom.

Most importantly, I would encourage LGBTQ+ people to go into education because our kids need those role models desperately. When I was a student, I had no gay role models at school, and I often felt excluded. No young person should have to experience what I experienced.

I want all students to feel safe and welcomed at school. Students flourish when they feel they belong. That’s why I do the work I do. I want to wrestle with problems. I want to create solutions for students. Doing so gives me meaning and purpose. It’s exhausting, but it makes me happy.