Get to Know our New Head of Upper School

Interviewed by Mary Courtney Finn

While we have gotten to know our new Head of Upper School, Mr. Montgomery, through his speeches at assemblies and observations in our classes, I wanted the student body to get to see a different side of him. We know things like his educational values, but we don’t know the fun stuff like his favorite music. I sat down with Mr. Montgomery to ask him some pressing questions about his life. 

What do you listen to on your ride to school every day?

I like to listen to music and it ranges from Foo Fighters, Grateful Dead, Cage the Elephant, and My Morning Jacket.

What is your favorite place you have visited? 

My favorite place I’ve visited in the world is French Polynesia. I went there on my honeymoon, and it was so beautiful. It was so far and felt like a different planet. Or Florence… I went when I was 12, and I got to try gelato for the first time. My parents let me go all alone to get it and I felt so grown. Also Salzburg, Austria was beautiful and gave off The Sound of Music vibes.  

What were you like in high school?

It depends…  junior year I made a conscious decision to test the status quo and found myself yearning for more than Montgomery, Alabama. I wasn’t rebellious, but I was gregarious. I definitely visited the principal a few times. 

Which celebrity would you want to play you in a movie?

Ooooh that is a tough question… It would definitely be directed by Wes Anderson, so it would probably have some of his casts acting in it. But I would want Owen Wilson to play me.

Your ideal day includes what?

I would wake up and commit to physical activity before breakfast– run or put myself through the extreme pain of a HIIT workout. Then have a nice piece of avocado toast with an egg and sriracha with dark roast coffee for breakfast. Then go to a small music festival for lunch, hang out with my family, and hear good tunes. I want to swim somewhere fresh (like a waterfall or lake), then go to a live sporting event, probably soccer. Finally, I would go eat really good pizza. 

What is the best piece of advice you ever received?

I have had different advice given to me during different times in my life, but my dad always said luck is when preparation meets opportunity. I always valued that and was never led to believe things happened by accident. Additionally, a colleague encouraged me to practice radical authenticity and made me want to be radically authentic.