20 Questions with Jennifer Borman '81, Commonwealth's Head of School

The first alumna to lead Commonwealth School, Jennifer Borman ’81 returned to her alma mater in 2021 with a wealth of experience in education, a field that has captivated her for nearly forty years. Whether leading an institution or a class full of inquisitive Commonwealth students, Ms. Borman has fielded plenty of questions in that time—though, perhaps, none quite like these.
Keep reading to learn her definition of success, her (alleged) celebrity doppelganger, the best gift she ever received, and the ideal number of ice cream sundaes one should consume in a day…

1. What three words best describe Commonwealth?

Inquisitive, engaged, and verbal!

2. What was your favorite Commonwealth class?

No one particular course, but I loved all of the times I left so many different classes with my head spinning from a new way of thinking about something.

3. What does your ideal afternoon entail?

A beautiful hike, an engaging book, and an ice cream sundae. Followed by a raucous family dinner and a second ice cream sundae.

4. Whom do you most admire?

I have long admired Charles Merrill [Commonwealth’s founder] and sometimes find myself silently talking to his portrait and asking what he’d make of a particular turn of events. I also admire Pete Seeger [folk singer and activist], who had a joyful way of bringing people together and a moral purity that always escapes most of us.

5. When and how did you first become interested in education as a career?

It was an accident. I was offered a teaching job at a school that had an unexpected opening. I was completely surprised by how much I loved it—and still do. It’s endlessly creative and so inspiring to see students grow. That being said, the best teachers walk around with a semi-permanent feeling of inadequacy: you always feel like it could have been better or you could have reached a particular student in a more impactful way. And beyond teaching, the same holds for leadership in schools: it’s amazing to create the context for growth and always humbling to know how much more you’d like to do.

6. What do you find is the biggest misconception about running a school?

I think people still have a pretty paternalistic, hierarchical idea about the role and that’s imprinted in our culture’s frame of reference. I am more interested in leading collaboratively and in models of change at the intersections between top-down and bottom-up initiatives.

7. What is your favorite aspect of your work?

The engaged conversations—whether with students, colleagues, trustees, parents, or alumni/ae. I also love the esprit de corps at Commonwealth and the shared sense of commitment and enthusiasm for learning.

8. How do you define success?

I feel like it’s our work and pleasure as humans to be able to frame our own definitions of success and then to continually revisit those definitions. For me as an educator, my success would be empowering young people so that they have the skills they need to walk through the doors they choose.

9. What are people surprised to learn about you?

I’m not altogether sure. People are too polite to tell me!

10. What book do you wish you had read sooner?

There are more books I wish I’d read later: I might have liked Hardy or Dickens better if they’d found me voluntarily. I’m very grateful to have read a lot of feminist work as a teenager; that’s been a lens that’s really important to my understanding of myself and my possibilities. 

11. Coffee or tea?

Both. In quantity.

12. Scripted or improvised?

Life pretty much defeats any script in my experience. Plan carefully and then respond in the moment.

13. What is your favorite museum?

The American Visionary Museum in Baltimore, the ICA in Boston, the Frick in New York City—and maybe whatever the next one is around the corner.

14. What is your favorite mode of transportation?

My feet. I’m still getting used to Boston driving. Ugh.

15. What do you bring to a potluck?

Enthusiasm. And some kind of dessert I’ve never made before because I like the suspense.

16. What was your go-to Boston eatery as a student?

The now-defunct Ken’s on Boylston Street, the site of lots of after-school conversations, debriefs, and speculations.

17. Where do you hope to vacation next?

In a mythical realm, I’d rent a series of month-long Airbnbs around the world and live as a local. 

18. What is the best gift you have ever received?

A wonderful education. Truly.

19. Who would you want to play you in a movie of your life?

I once got into a long argument with a stranger who was convinced I was the talk show host Ricki Lake and thought my denial was Ricki Lake denying she was Ricki Lake. That soured me on the whole concept of celebrity doppelgangers.

20. What is your motto?


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