Feels Like Home: Our New Headmaster’s Thoughts on His First Semester


Ariel Levine

Steve Bileca, the new headmaster at the Vail Mountain School

Owen Cruz-Abrams, Staff Writer

October 26, 2022 – A man who is clearly passionate about education and his students, Steve Bileca, the new head of Vail Mountain School, aims to bring “a sense of energy, joy, and wonder to the educational experience.” Mr. Bileca comes to us from Hackley School in Tarrytown, NY. At Hackley School, Mr. Bileca held the esteemed position of Assistant Head of School for Academic Affairs for six years. Prior to that, he served as the Director of Middle School there. He “already [sees] a lot of [joy] here at VMS” and seeks to continue to grow the student body’s enjoyment of learning. Bileca played a crucial role at Hackley School in assisting students. As The Dial, Hackley School’s student newspaper, reported, “He made me feel welcomed, and doing the crossword also helped to become closer as an advisory even when it was harder to make connections because of the pandemic.” During our interview, Mr. Bileca agreed with this statement, saying that one of his priorities was to “foster teacher-student relationships and student-student relationships,” and “[carry] a sense of generosity, of realizing that faculty and students each have a lot to learn from and offer one another mutually.” The new Head of School stresses the importance of education in developing the next generation; “I believe so deeply in what schools do for students, and so deeply in what teachers bring to their work.” Bileca also believes deeply in the VMS mission, and noted how important the pillar of Community is, and how connected it is to that of Character; “Learning in community is how, as human beings, we learn best,” and that we should “[learn] from different perspectives and points of view in our own community and in our wider world.” Complimenting the vast environmental learning opportunities at VMS, Bileca “Our connection to experiential education inspires me, and what we gain from that is a sense of our own ability and [discovering] hidden reserves that we didn’t know we had.” On rewarding academic achievement, Bileca is “of two minds…on one hand, I think it’s great to give students and us all something to aim for.” However, he also thinks that “sometimes, extending ‘rewards’ for achievement can be detrimental, especially for older students, because it can sometimes have the unanticipated effect of demotivating students to achieve for intrinsic reasons, rather than for the ‘external reward’.”  


Interviewer: If I were to give you a million dollars and you had to donate it to one part of the school, what part would you give it to? A specific subject?


Bileca: I can foresee several areas where I would want to put the money. One is access and affordability, as independent schools come with tuition, and sometimes that is a stretch for families, and I would love to be in a school where I was certain that everyone who wanted to and deserved to be here could, regardless of their ability to pay. Similarly, I think a number of our programs are really remarkable, and I could see wanting to amplify some of them – some of the academic programming as well. I think our building is beautiful and our campus is gorgeous, and I could also see, though I don’t know if this is where I would put the million, wouldn’t it be fun if we had a remote campus somewhere? Wouldn’t it be fun if we owned some big wilderness somewhere, maybe an hour or two away, where we could go off and do all of our wilderness adventures? It’s fun to dream!


On the topic of sports, Bileca is animated. “Oh my gosh, so I’ve got at least three. To participate in, I love cycling, both mountain biking and road biking.” An avid skier, Bileca loves “snow sports, I love skiing, and this year I hope to try snowboarding, because I’ve actually never tried it!” The Head of School enjoys “three flavors of skiing, downhill/alpine, cross country, though I don’t compete in either of those. I also just in the last couple of seasons took up skinning and backcountry skiing, which I’m so looking forward to this season.” Mr. Bileca also loves to scuba dive, albeit without many opportunities in Colorado, due to living in Florida for some of his life. 

Interviewer: If there was one thing you wish all students knew about you, that you wish you could tell them, what would it be?

Bileca: I wish that students knew, well, a couple of things. One is how happy I am to be here in this school – it has felt like home from day one, and I think part of that is the things that are important to me. One thing people may not know about me is that I am in love with music, and I listen to all kinds of different music, from jazz to classical to world to blues and rock, and everything in between. I play music with my two sons, and some of the most fun we have is playing music together. I enjoy playing blues harmonica and flutes, and there is almost no kind of music I don’t enjoy. It’s essential to listen and be exposed to different kinds of music, just like different perspectives, because you always learn something. I love the idea that we can travel in our minds, we don’t always necessarily have to travel physically, so that we can be aware of other people, other countries, other parts of the world.


Foreign languages are of no less importance to the new Head of School, “because I think they help us be more aware, sensitive human beings – and it is great fun to be able to hold conversations in another’s language!” A true polyglot, Bileca speaks English and Spanish, along with German (which he learned while living in Germany) and Italian. He has basic skills in French and Hebrew, and has just started “taking lessons in a very obscure language in the Balkans, native only to about a million people, which is the language my grandparents and father spoke.” 


The mission of the Vail Mountain School, Developing Character, Seeking Knowledge, and Building Community, was “one of the things that attracted [Bileca] to VMS” because of the “beauty and precision” of it, as the mission is the “most memorable of any school at which [he has] been.” Though Bileca sees the mission as interconnected and each pillar to be of equal importance, he also believes that developing character, which is first in the mission, “is what gives purpose to our education,” for if we did not develop character, “the knowledge we impart might not be put to wise ends. We all know the stereotype of the ‘evil genius’.” Therefore, Bileca thinks that “developing character is super important, along with seeking knowledge, as we want to put that knowledge to a particular end which we hope is good. Both of these things only happen in community.” Bileca believes that to learn from mistakes, you should be in a “strong, loving community,” one which he believes the mission of VMS intends to provide. “I really see the three as completely interconnected.”

When asked about behavioral discipline, Bileca wants to provide “moral exemplars by the adults in the school behaving in a way students recognize are the ways they ought to be behaving, just as our older students model for the youngest. We need to be conscious of our roles as moral exemplars.” Responses to mistakes “should always be educative, to help the student realize how to grow and improve.” The Head of School profoundly recognizes that as humans, we will all make mistakes, and it is essential to have people set you back on the right track. “We seek to help people develop moral character in a way that does not feel overbearing or tendentious.” Mr. Bileca sees the Kindergartener-Senior buddy program as an opportunity to model character for younger students, and “we see the younger students receptive to that behavior in a way that’s different from their reactions to adults, as they want to be like the eleventh and twelfth graders.” He also sees the program as “a very special feature of this school.” 

Bileca appears to have a fantastic approach to education, and we cannot wait to see what he will do at VMS.