Get to Know Jay Rainey

Our new Head of School sat down to talk education, entrepreneurship and 21st century St. Louis.

Why are you excited about this position at MICDS?

Sandra Polanco ’20 and Jessica Brooks ’20 present Mr. Rainey with a variety of St. Louis t-shirts.

I feel honored, probably more than excited – extraordinarily honored and privileged to lead such a strong and manifestly aspirational independent school.

What is eminently clear is the strength of the faculty and staff at MICDS. Connected to that is the relevance and currency of the curriculum and the strength of the extracurricular program, especially the arts and athletics programs.

Recent fundraising through capital campaigns was extraordinarily successful, so the School has seen significant facilities and endowment growth. Our endowment is the greatest bulwark against one of the biggest challenges facing independent schools: affordability.

I have also observed former Head of School Lisa Lyle’s keen interest in having the School’s student body mirror the heterogeneity and reach of the St. Louis community. I am committed to making MICDS a welcoming place for students and families of diverse backgrounds and interests. Schools are more relevant and stronger when they reflect the communities they inhabit, and students are better prepared for the expansive world that awaits them.

What do you think makes MICDS stand out from other schools?

Mr. Rainey connects with Middle School students when he visited MICDS in the spring.

The age and history of the school, with its deep roots and time-honored traditions, make it stand out. Schools have to be at once current, relevant and reflective of today’s society and the world and its expectations, while also remaining connected to families who have sent their children here for generations. MICDS gets both of those things done.

MICDS also stands out for its JK-12 program, which is distinctive in the St. Louis independent school marketplace. MICDS is a family school, a school that understands children from their very earliest years as learners until they’re ready to graduate.

I also think MICDS’ culture of philanthropy is a unique strength. There’s such a strong love of the School among so many alumni and parents, even grandparents. That’s essential to the health of the school.

What do you think about moving to St. Louis?

As a history buff, I am well aware of the importance of St. Louis in the 19th Century, from westward expansion to the Missouri Compromise. When you’re in the city today, you can see its age, just by dint of the architecture alone and the layout of the city. As a former English teacher, I love that MICDS was founded by T.S. Eliot’s grandfather.

In terms of St. Louis today, I’m aware of the challenges the city has faced—including the sale and relocation of corporate leadership and the resulting economic adjustments—and the exciting transformation the city is currently experiencing.

I’m interested in how America’s conflicts and points of discord come home to Missouri. Tackling tough issues can be healthy, because you can’t run away from issues that are right in your community. You have to come to the table and work together. I’m excited to be a part of 21st century St. Louis.

What do you enjoy doing in your spare time?

I love to read. I think it’s an obligation of a head of school to be well-read. I hope to find some way of sharing what I’m reading with the community. I play the piano to relax. Old jazz standards and pop songs are fun to learn.

I also love to ride my bike. I hope to start golfing, and maybe get back into tennis because it’s such a great sport.

I enjoy watching baseball and listening to a well-called game in my car or in the background. The strategy and pace of baseball are so fascinating. It’s like chess on a playing field. With a raucous crowd. And hot dogs.

Tell us about your family.

Jay and Ruth Rainey with their children, Elizabeth and Jed.

Ruth and I have been married for 21 years, and we have two children. Jed, a senior this year, was born in Chicago. Elizabeth, a sophomore, was born in Norfolk, Virginia. We have a really wonderful family life. We’re close, and it’s been nice to watch the kids grow up and become their own people. We also have a lovable, but lazy, English bulldog, Silas.

Jed and Elizabeth are at boarding schools. They’re happy to have schools where they’re just normal kids, not associated with the head of school. When they’re home, they will be visible in the MICDS community. They’ve already made friends here and lined up summer jobs at MICDS – Jed as part of the grounds crew and Elizabeth as a Pegasus camp counselor.

How did you come to lead schools?

As a teenager I gravitated to work with children. I worked at the local YMCA as a coach and day camp counselor. As I got older I moved into leadership roles. My mother is a retired lower school teacher, so I saw teaching modeled in her.

When I went to college I taught math SAT classes in high schools around central New Jersey for The Princeton Review. I loved the experience of teaching, of working with students. I went back to Virginia and created my own SAT prep business.

At the end of my senior year of college, I decided to go into teaching, and after graduation I worked for one year as an English teacher at Hampton Roads Academy, a small independent school in Virginia. I liked the work, but I decided to move to Richmond and started another company. I persuaded an angel investor to fund an internet start-up that hosted an online portal for teachers to share resources and lesson plans. My company didn’t take off, but it opened the door to an opportunity to move to Chicago for an education company that was adapting its products for digital and online delivery.

After working in the education market but not in a school setting for seven years, I realized how much I missed direct interaction with students. I left Chicago for a position back home in Virginia. I taught English and Math, served as a swim coach and even advised the yearbook staff. Eventually I moved into administration, starting in college counseling and then overseeing curriculum design and advancement, library and media services and even IT. That led to an assistant head position, and then to the head of school opportunity at Randolph School.

My intellectual life was formed early and heavily, and I’ve always wanted to teach and to be around young people. My experiences as an entrepreneur taught me to be thoughtful about design, innovation and opportunity — to always be looking for a better mousetrap.

So, in a nutshell, I’ve come to lead schools because of three things: a love of children, a love of the life of the mind and an entrepreneurial inclination that seeks forward momentum.

What will be your priorities during the first year?

Jay meets with Upper School students during a campus visit in March 2019.

My first priority is to observe and to listen. I want to take the measure of MICDS across the three divisions and all other areas of school operation. I plan to receive as much input as I can. I’m looking forward to the ISACS self-study this year, a process that will allow us to be reflective and thoughtful about our work together. Through conversations already well underway, I’ve learned about challenges and opportunities in a variety of areas. I want to join with faculty and staff to tackle identified initiatives for improvement.

I’m not coming in with a handful of to-do’s that I think need to be executed on in my first 100 days. MICDS is not a fixer-upper; it’s not a school in distress, and it would be the acme of hubris for me to come in and say, “I know what’s best.”

Everyone who comes to a school in whatever capacity should feel good about themselves and their community. I hope to enable and promote that kind of atmosphere. The work of a school should be about lifting up every child in its care.

I hope to set a tone for reflection and to be an effective communicator as part of my leadership style at MICDS. Policy and strategy will come in time, but initially I will be leading more in terms of tone-setting.

What is your philosophy on leadership?

I can sum this up in two quotes. The first is, “Be kind, for everyone you meet is engaged in a great battle.” It has to do with an understanding of leadership as essentially and inherently relational. It’s important not to judge or be cynical.

The second quote is from computer scientist Mark Weiser: “The most profound technologies are those that disappear. They weave themselves into the fabric of everyday life until they are indistinguishable from it.” I think great leaders are that way. They lead almost invisibly. Great leaders set the tone of the organization. The culture they help create is this kind of profound technology that people can depend on and trust that it’s working and healthy.

Can you speak to your thoughts on diversity, equity and inclusion? Why is this important in schools?

There’s a three-fold mantra of learning and growing, individually and in community with others, that I will express as frequently as possible at MICDS: Always reason, always compassion, always courage.

Respecting the first of these, great schools like MICDS are nothing if not sites of intellectual formation and the cultivation of our capacity to think critically and objectively. We have an unfortunate propensity as a species to be tribal — to diminish or to exclude those who appear to be different than we are — and to defend our beliefs however baseless. But unthinking intolerance and narrow-mindedness cannot survive a culture that elevates reason as an essential quality of mind, that teaches young people not what to think but how to think, that values hard questions more than easy answers. Reason is the antidote to our confirmation bias and our tribal instinct to label, disparage and even dehumanize other people in terms of their surface differences, because it is the means by which we realize how much more unites us than divides us.

The next word in the mantra, “compassion,” literally means “suffering with.” Compassion allows us to move out of our minds and into our hearts. MICDS is and must continue to be a place where students get to know each other and therefore open themselves to perspectives of empathy and compassion very naturally.

Finally, as for courage: I hope to set an expectation of MICDS students that they act on their moral compass, that they act on their best judgment, that they act on their compassion and kindness and empathy for others.

We need to help children be the most thoughtful, empathetic and courageous people they can be. It’s about nothing less than a culture of prevailing human kindness. Racism is real and bigotry is real. If we can create an environment that provides no safe harbor for irrational stereotypes or prejudices, for bullying or meanness, for cowardice through inaction — if we can always emphasize reason, compassion and courage — we will be doing diversity, equity and inclusion work in the most authentic, character-forming and universal ways.

Can you talk about the importance of collaboration?

Healthy collaboration follows a very strong sense of community and mutuality. Collaborative people place value on diverse perspectives and approaches and ways of being in community. The more that we can do to spread goodwill throughout the MICDS family, the more that healthy collaboration will be second nature.

Thanks, Jay. Are there any other thoughts you’d like to add?

I understand the scale of the challenge of leading an institution with such high standards and such a powerful legacy. I am very hopeful to earn over time the trust and affection of the School community.

A leadership transition is an opportunity for a school to take stock of itself. It surfaces a lot of passion about where the school is heading and the work that it needs to be doing. I intend to make the most of this opportunity on behalf of the entire school community. I look forward to leading MICDS into the future.