
Shawna Hennessey has been an Italian instructor at Fenwick High School for 19 years. Affectionately referred to as “Prof” by her students, she teaches with genuine enthusiasm and commitment. But if you had asked her two decades ago where she’d be today, she never would have imagined the role she’s come to love so deeply.
Hennessey was born in Minneapolis but grew up in Western Springs, a southwest suburb of Chicago. Though her father is mostly of Irish descent, her mother traces her roots to Amaseno, a small town in the Lazio region of Italy. Hennessey’s maternal grandparents immigrated to America in the mid 1900s, settling in far south suburban Chicago Heights.
Hennessey has had plenty of opportunities throughout her life to develop a strong attachment to her Italian heritage. “My mother is from a huge family,” she recalls. “We always spend our holidays together.”
She took French in middle and high school, but yearned to take Italian, which wasn’t offered at either location. “I always wanted to learn the language that my mom didn’t know,” she says. “She was frustrated that she was never spoken to in Italian and couldn’t learn it.”
Hennessey majored in graphic design at DePaul University, minoring in Italian to pave the way for a semester abroad in Rome. “I really wanted to study art history in the birthplace of the Renaissance, so I took the language that would allow me to study art in Italy,” she explains.
She recalls loving every moment of her stay in Italy, where she gained invaluable experience speaking Italian. After graduating from DePaul, however, she put those skills on the shelf, taking a job at a small downtown law firm. She might have remained on that path, but an opportunity arose that completely redirected her life.
At the advice of a former teacher in Italy, she took a job teaching math, science and other courses in English to Italian students at the Istituto Superiore, near Milan. The experience transformed her linguistic abilities.
“I went there comfortable with the language because I had a minor in it, but I attribute all of my Italian skills to living there,” she says. “It put me in my students’ shoes.”
After a full academic year abroad, Hennessey resumed her job at the law office in Chicago, going back to Italy often to visit her “adopted mother” and close friend.
“She’s a very generous woman. I would’ve been so lost without her,” she says. “She always invited me to dinner and introduced me to everybody.”
A short time after Hennessey’s return to Chicago, a colleague told her about an opportunity to teach Italian at Fenwick High School, a private Catholic college prep school in west suburban Oak Park. Embracing the prospect, she looked into the position with an open mind and has never looked back.
Hennessey has taught every level of Italian available at Fenwick, from beginner to Advanced Placement, as well as beginner French. The most important aspect of teaching, she says, is providing a welcoming classroom environment, and the biggest challenge is understanding that not every student is “all in.”
“I have to remember that my class is not the center of their lives,” she explains. “There are so many circumstances and situations that people come from that can make giving my class their full attention very difficult.”
Her solution? Do everything possible to make each new day of class a unique and engaging experience.
“I love that none of my days are the same,” she says. “I don’t know what to expect. I can have a plan and throw it out the window because I listen to my students. They tell me where I’m going and guide the lesson.”
Hennessey regularly enhances her lessons with speaking exercises and emphasizes the importance of returning to the one place where you can truly master the language. She recently took a few of her classes on a trip to Italy, immersing them in non-stop encounters with native Italian speakers.
“Students would say to me, ‘I spoke to them and they actually understood me’ and I’d reply, ‘I know. I’m not teaching you a made-up language’ but it was just so rewarding to see that,” she says.

Hennessey has transformed the Italian culture at Fenwick. Under her watchful eye, the Italian Club has emerged as one of the school’s most popular: a place where students can gather to prepare and enjoy traditional food and connect with time-honored virtues.
She’s looking forward to taking the club to fulfill service hours at Casa Italia, an
Italian-American community center in nearby Stone Park.
Witnessing her students’ progress is the most meaningful part of teaching for
Hennessey. Any headway a student makes, whether it’s reaching fluency or just getting comfortable with some of the language, brings her a great sense of pride and joy.
“But it’s also the kids that don’t end up fluent and feel like they can’t do it, then all of a sudden, it clicks,” she says. “It’s rewarding to see that they’ve pushed themselves far enough to learn something.”
Fra Noi Embrace Your Inner Italian