“I’ve only cried tears of pure joy two times in my life: one would be getting into Wharton, and the other would be getting my McKinsey offer,” Isabella Anastasoff (W’ 19) says, raking her hands through her hair, fighting the wind. “I hate to tie my highest high...of Penn to career only,” she insists, while sighing somewhat halfheartedly. I find this admission surprising because she truly loves business.

For Isabella, pitching to venture capitalists was something she learned at an MIT summer program in 10th grade. She works part–time at a private equity shop here in Philly while finishing senior year. She’d even qualify an anthropology course on “the study of corporate cultures” as her class most “off the beaten path.” 

Born to two Bulgarian immigrants living in Southwest Chicago, her early childhood wasn’t exactly a cakewalk. Her dad suddenly left the picture when she was two while her mom was still completing her residency to become a pediatrician. She tells me, though, that “Chicago doesn’t believe in tears,” a saying that she repeats several times during our conversation when talking about some more difficult topics. 

Her mom raised her to be tenacious. A sort of self–assured, focused, but not overconfident rigor underpins Isabella’s words, perhaps influenced by her mom’s own drive while juggling a small child, a job, and residency. She also speaks with a sort of gentle, almost breathy voice. “Picking yourself up, dusting yourself off, and figuring it out,” she says, explaining the maxim, “you just have to figure out like, tears, cry it out yeah, but then you have to pick yourself up again.”

When talking to Isabella, it’s clear that her zeal for business has a lot to do with her mother and this “Chicago doesn’t believe in tears” mindset. She describes one time when she was anxious about taking the ACT in high school, her mom took her on a drive through downtown Chicago to ease her nerves. Coasting through traffic at sunset, taking in the might of skyscrapers and glamorous urban life, the car rides with her mom helped her “get motivated to work hard so [I] can live in one of those penthouses and work in one of those buildings.” She still loves Chicago, a city she even plans on returning to after Penn.

Photo: Ethan Wu

Isabella’s résumé is pretty impressive. Inspired by the sacrifices her mom had to make in order to raise her, she is the type of person who wants to suck the marrow from her time at Wharton. She’s concentrating in finance, statistics, and marketing—a mix directed partly by her affinity for private equity, and partly by a professor who told her that statistics is integral to the future of business. She also is a member of MUSE and Ivy Capital Management.

But Isabella also lacks the hardened veneer so many post–OCR Whartonites have. She lights up when talking about mentoring the younger members of MUSE and expresses disgust at some of the over–competitive tactics others have used to get ahead—like telling her the wrong room number for an information session on purpose. Although her “Chicago doesn’t believe in tears” mindset may seem like a tough front, she talks about her friends with affection, chuckling as she fumbles through a story about how she and a friend bonded over typifying the drunk people at Center City Sips during the summer.

It’s this kind of subtle jubilance that makes Isabella’s biggest regret of Penn inspire a similarly subtle sense of wistfulness. She feels like her social life here exists in flux between a collection of smaller, one–on–one friendships, instead of being structured by a large friend group. That’s not to say she doesn’t appreciate the friends she has, Isabella assures me, but rather that she feels as though she didn’t really choose to join any social club in college that could be just for fun. Instead, she says, “academics, and opportunities, and things that you could put on a résumé were what came first because so many sacrifices had to be made on my mom's side in order for me to come here.”

What clubs might Isabella have wanted to join? Well, kickboxing or beach volleyball, for starters. She loves the high–energy release associated with either sport, perhaps as an outlet for some stress accumulated through her studies.

What’s more, her love for beach volleyball emerges from somewhat of a friendship meet cute. It starts like this: Isabella stayed on campus freshman summer, and was introduced to Meghan through a mutual friend. Meghan, who loves beach volleyball, asks Isabella to play on Drexel’s sand courts one evening after hearing that she’s played before on vacation. What follows is what would become, and still is, a regular date. Any time they have a free afternoon, they walk over to the sand courts on Lancaster and play pickup games. 

The best thing about the courts, she says, is that they’re open until, like, 11 p.m., so in the summer they can play well into the evening; far better than Sigma Chi’s court on campus. As she tells me all about the rules of beach volleyball on the sidelines of Drexel’s courts, Isabella points at some shirtless guys in the middle of a volley at the far side with a grin, adding “and we can hold our own against pretty much anyone now, we even almost entered a beach volleyball competition in New Jersey.” 

So, what lies in the future for Isabella? It really depends on what you mean. Professionally, she starts at McKinsey in Chicago after summer ends. Romantically, she has a long–distance boyfriend who just happens to be moving to the Windy City around then as well. And, on the side, she wants to start an Instagram for women entering and navigating professional development, inspired by her own mentors who have helped her her penchant for lifting up others. Maybe she’ll pursue private equity or exercise her entrepreneurial desires in the long term. Her interests are deep and varied, while also focused mostly on professional success.

One thing is for certain, though. Isabella isn’t really looking back. I picture her twenty years from now, living in Chicago, on a drive through the city she knows as home. Her mom is with her. Maybe Isabella’s stressed about closing some big deal or maybe it’s something else. But, her mom is telling her, “Isabella, Chicago doesn’t believe in tears.”