Career mentoring expedition: July 13-19, 2025
Written by: Janean Shedd
“I can see myself working at Conagra, or a place like that.” “I thought it was really cool that those women didn’t really know what trading was but went for the job anyways and learned it.” “I loved the kayak tour.” “I’m a band kid, so the jazz show was the most memorable moment for me.”
That would have been some of what you heard if you’d been at our final community meeting this past Thursday night as we sat outside on the patio in Wicker Park, closing out our Chicago trip with our 12th grade cohort from Newark High School.
These nine girls (who, along with three others are in a leadership and career mentoring program at the high school) had planned and executed this culminating trip, and we spent the last few moments in the city wrapping up everything from the week. We talked about the most impactful people/places, most memorable moments, and took the time to affirm one another’s strengths. The girls spoke about hearing how important networking is (and recognizing that they, “get it,” now), and about how impactful it was to meet people who worked jobs they were passionate about. They had met someone from Victor, NY who is now a large event planner in a large corporation in a major city, and another woman who had aged out of the foster care system in NYC, needed to find a way to feed herself, and now found herself leading the pastry team at the same place. They spoke of the calmness, kindness, and leadership skills in those they met, and in each other. It was, I believe, a truly impactful trip overall. But, perhaps starting at the end isn’t quite how to share this so…
Sunday, July 13th. Train Station. Rochester, NY.
Both by van and by car, 9 teenage girls and 3 adults showed up to the train station in Rochester, NY…only to find that their train was going to leave 2 hours later than planned. And so, a good lesson in mass transport, how to rest in public spaces, and how to occupy oneself was had.
Monday, July 14th. Riverside Plaza. Chicago, IL.
Fourteen hours later, that same group left the train in Chicago, IL, and the girls began to take lead on subway and street navigation. After settling into the AirBnB and freshening up, we all went to Belvedere Trading Company to meet with many of the women who work there. Belvedere has a strong women’s initiative as a part of its mentoring system and so it was not only the female leaders who showed up to share their stories and advice with us, but 
many women, from managers to interns, coming to share that it is possible to jump into
a career that you know nothing about, and learn it as you go. They came to share that passion to grow oneself and the ability to network can get you far as a professional. They came to share time and refreshments and to offer their faces to a space to show our girls that, yes, they can belong in spaces like this, no matter what they look like or what their backgrounds are. Whatever they want to pursue, whether it’s a male-dominated field or not, if they are passionate about it, they can get themselves there.
Tuesday, July 15th. Wicker Park. Chicago, IL
Everyone needed rest after all the traveling, and so, after a slower morning, this group of courageous girls set off for RPM, of Lettuce Entertain You, Inc. They had a tour of 3 of the original concepts, each with a female manager showcasing the space, sharing about her career path, and making the girls feel right at home with a cold drink at one stop, an appetizer at another, and lunch at the third.
The whole experience was clearly curated to help them feel at home and to give them a sense of belonging if they so chose to accept. After a fun pastry craft to take home, it was time to explore a bit. The riverwalk gave them more perspective of the city, and a chance to stretch their legs. Some spontaneous plans helped guide them to making more full-group decisions in the future, and an appreciation for just how much the city has to offer (they walked until people’s feet and legs were sore, and then had to walk more in order to get back home!).
Wednesday, July 16th. University of Chicago. Chicago, IL
The morning found us on a longer subway ride to go see the University of Chicago. After an unexpected tour of the athletics building, a quick visit to the central quad to get a feel for the campus and a library visit, we set off for Conagra.
At Conagra we were greeted by the director of behavioral science, who introduced us to a few other women (including a lawyer and the director of research and development). These women talked mostly about networking, and about how their skills transferred from one job to the next within their fields. They spoke about trying new things and pushing themselves to grow and learn. From the 13th floor of Merchandise Mart the girls watched as the four women who were present talked about how to weather difficulties in the workplace, by leaning on and learning from those around them. (They also watched a terrific storm rage outside, shifting the weather from blazingly hot and humid to much cooler.)
Thursday, July 17th. Wicker Park. Chicago, IL
A quick bus trip took us to our kayak adventure for the day. The architecture tours of Chicago are famous, but most happen on a boat. Our girls had requested that we do the kayak tour, and see the city a bit more intimately. Our main guide (an ecology professor from De Paul University) shared architectural and ecological information on the way. 
More importantly, though, he consistently repeated that diversity is the key to everything working well, and shared about the joy he has found in working jobs that he enjoys and is passionate about. The tour ended with some cold heavy mist, and though everyone seemed ready to be done for the day, some girls had discovered that they loved kayaking! Others, who had been fairly nervous to begin with, found a new source of pride in recognizing all the nervousness and physical challenges that they had just successfully navigated through. You might think that would be enough for the day, but we had one big stop left.
Chicago is known for jazz, and many of our older cohort girls are involved with music and theater at the high school. It was only right that we had a celebratory dinner out at Andy’s Jazz club to end the week. The jazz quintet had sweet sounds and good charisma. The end of the evening found the lead musician in conversation with half the group after another patron made it a point to tell him that we were a high school group from upstate, NY. Some late evening adventures in the neighborhood near home finished the night.
Friday, July 18th. China Town. Chicago, IL
The girls had saved the last day for fun and sightseeing. We all knew everyone would be mentally spent by this point in the week, so they had planned a chill day before taking the train back home. The Medieval Torture Museum was first, followed by China Town. 
The girls were almost fully independent now. None of the facilitators were looking up directions, and we only once had to stop the group to make sure everyone knew the plan. The girls were a well-oiled machine: navigating the city confidently and safely, and communicating intent with the whole group. One last chance to wander in our Wicker Park neighborhood and one last dinner together led us to that closing conversation where we all got a chance to hear about the growth from the week.
One last subway ride and walk through downtown (complete with a car stopping at an intersection to wish us well on our journey) led that tired, proud, accomplished, and wiser group of humans to the train station. 12 hours later, we would arrive back from whence we came.
Saturday, July 19th. Train Station Rochester, NY
Tired and glad to be able to rest at home, and also grateful for the adventures, 12 people made their way off the train. It was the same group that left, but they were no longer the same people. The growth in self-awareness, self-confidence, communication, and conflict resolution skills had shaped them into more of the fullest versions of themselves-both teens and adults alike. As adults, we are honored to have been able to take this journey with them, grateful to know them as much as we do, and eager to see what paths these female seniors take this coming year, and, ultimately, what they choose to do with their lives.
