Jose Ruiz: From Edgy Teenager to Dean of Students
By KENDELLE GRUBBS ‘20
The Dean of Students José Ruiz fills the room with standard small talk as I set up for our interview; questions about my classes and workload drown out the sounds of my keyboard clacking. With everything set up, I ask for permission to record our conversation, and he readily agrees.
I start out with the question that sparked the interview: how did his experience in boarding school differ from the experience of students at Milton?
Ruiz spent his high school years at Westminster School in Simsbury, Connecticut: a small town thirty minutes from Hartford. One of the key differences between Milton and Westminster is the amount of people; Milton’s upper school consists of about 700 students, and adding faculty and staff brings the number up to almost a thousand people, which is a community much larger than that of Westminster. “Here I sort of feel like with the K-8 division there’s a lot of bodies on campus,” Ruiz adds.
One might assume that a smaller campus would equate to closer relationships between members of the community, especially in the dorms. However, Ruiz’s boarding life didn’t have any sentiment of brotherhood and sisterhood—an element of life at Milton that most borders greatly appreciate. Ruiz remarks that he didn’t feel like he had “the intimacy” that boarding students here share during their four years. Instead of being randomly sorted into one dorm for all four years of high school, as is the case for Milton, students at Westminster choose their dorms and switch every year.
On the topic of dorms, Ruiz describes an emotion familiar to every border: homesickness. Although Westminster tried to help new students feel welcome with new student programming and a “corny”—yet helpful—square dance, Ruiz still felt distant from his community. He “didn’t feel truly comfortable” at Westminster until the end of his ninth grade year. “From September until December, I would talk to my parents every night,” Ruiz admits, “So I was homesick. Definitely homesick.”
Despite these differences between Ruiz’s experience and the Milton one, Ruiz is grateful for his boarding experience because, though it was uncomfortable at times, it helped him become a better advisor during his future time at Milton. Working with half of the juniors in Norris House, Ruiz provides helpful advice and listens to the student’s struggles with empathy.
Building on the juxtaposition between Westminster and Milton boarding life, I ask how a young Ruiz would fare in Milton’s vibrant community. He confesses that he would have felt more comfortable here, since Westminster did not have “the level of diversity that Milton has.” Ruiz describes himself as an “edgy” teenager with “a chip on his shoulder” who fought an uphill battle against the “unwritten rules” of Westminster. Milton’s culturally diverse atmosphere would have spun a very different tale for young Ruiz.
Like Milton’s familiar “Dare to be True,” Westminster’s motto of “Grit and Grace” provided a message of diligence and responsibility. The grace aspect helped him “be a better human.” Ruiz adds, “there were a lot of things that I didn’t like of the senior classes before me and so, from a graceful standpoint as a senior, I knew what I didn’t want to do.”
Shifting away from high school, his recent life had explored a fortunate chain of events. Ruiz returned to work at Westminster, but after ten years he forced himself to make a decision: either Westminster would be the only school he’d ever experience, or he would branch off towards a new path. Ruiz chose the latter, and found himself working for three years as the Associate Dean of Students at St. Marks. After former Milton faculty members Miles Bailey and Bridget Johnson approached him, Ruiz applied for his current job.
Now, Ruiz resides happily as Dean of Students providing support and guidance to all who need it. Make sure to pop by the Dean’s office if you ever want a nice conversation with a man who used to be a student, dealing with all the ups and downs of high school, just like you.