The student news site of Brookline High School

Kelly De Oliviera

Winthrop House English Teacher Kelly De Oliviera has built a career she finds great joy in through combining her passions. Her days are packed with the realities of being a loving mother to three children and a brand-new puppy, a high school teacher and a new co-entrepreneur with her husband.

What is it like to teach at Winthrop House?
I have been at the Winthrop House for seven years now working as a paraprofessional. This is my first year teaching English. Winthrop House is an amazing community, and we are a really small program. At any given time we can have up to thirty kids enrolled and that encompasses all four grades. I think that’s a really unique and big part. We also do a lot of cool community activities with our students, away from academics, which is really nice.

Have you always known you wanted to be a teacher?
When I was younger, I remember thinking how I definitely wanted to do something as a writer. Then, I got far away from those dreams. Eventually I had a bachelors in physcology and I really thought I wanted to do something in that field, like therapy or guidance counseling. Then, a job opened up at the Winthrop House. I found I actually really liked being in a classroom and teaching. I applied for the job, and it’s been everything I thought it would be and more.

Have you ever wished you did more with writing individually?
Yes, but then life got crazy. I had three kids and life took me in every other different direction away from my writing. I have always been a reader so I’ve always loved that part. I think I have a little journalism in me. When we went into quarantine, I actually started the Winthrop House Newsletter. I’m trying to convince my students to take over now.

How did you spend your summer?
This summer we actually opened a family business. My husband teaches Brazilian jiu-jitsu and martial arts. We opened a mixed martial arts gym. My three girls and I have been working with him to open the gym, helping run the classes, sign up members, cleaning the gym and things like that. It’s been a really big family project.

Outside of school, in your free time, what do you enjoy doing?
I love yoga, and we do a lot of hiking as a family whenever we can. I love reading; I need to be reading something at all times, but I don’t always have time to read books. When I can’t read books, I read magazines, and I love cooking too.

What’s your favorite book right now? Any recommendations?
Over the summer I read “Untamed” by Glennon Doyle. There are revelations in every chapter that you can apply to life. Her big message is “we can do hard things,” which we’ve embraced as our motto at Winthrop. It is okay to feel anxious or be nervous but we can still do this. That was a great book but my favorite of all time is “To Kill A Mockingbird.” That has been my favorite book since junior year of high school.

Do you have any important memories or lessons from high school that you would want to share with your students?
My time in high school was complicated. But I distinctly remember a meeting with my guidance counselor. He looked at my transcript and looked at my background and he said that I could be a hairdresser. I think after that, I decided I wanted to be a guidance counselor just because this person was so awful, I mean who says that to somebody? It wasn’t the best time of my life, but I’ll always take away that lesson: that you don’t ever diminish someone, not based on their grades or where they’re coming from or anything.

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