In the first Young Alumni Q&A spotlight of the Shipley Class of 2020 series, Caroline Milgram ’20 reflects on her path from Shipley to her current role as an Underwriting Analyst in New York City. Joining Shipley in 9th grade, she embraced extracurriculars like Student Government and theatre, while developing perseverance and self-advocacy. Caroline credits Shipley’s supportive environment with helping her navigate challenges, including transferring universities, and preparing her for success at the University of Pennsylvania and beyond.

Quick Facts
Colleges attended

• Northwestern University (2020-2021); Major: Economics
• University of Pennsylvania (2021-2024); Major: Philosophy, Politics, & Economics, Minor: Business Economics & Public Policy

Internships, awards, or honors received since graduating from Shipley

• Graduated Summa Cum Laude from the University of Pennsylvania 
• Dean’s List all four years of Undergrad
• Named one of UPenn’s Class of 2024 “Penn 10”
• Elected to Penn Student Government’s Undergraduate Assembly
• Internship at the Bank of New York Mellon

Q&A with Caroline Milgram ’20

How did Shipley prepare you for college? Can you share a little about your decision to transfer colleges after freshman year and what that process was like?
Shipley prepared me for college by challenging me to think independently while encouraging me to strive for greatness and take advantage of the opportunities around me. During my time at Shipley, I had to learn to balance a heavy course load and a wide array of extracurricular activities. I learned to manage my time well and to work through obstacles that came up. Most importantly, I learned to persevere and work through difficult things.

When COVID happened and I had to attend my freshman year of college virtually, I needed to adapt and learn how to adjust to a very different learning environment than I was accustomed to. After my freshman year at Northwestern University, I transferred to the University of Pennsylvania, which was very challenging. I had to adapt to a new environment and play catch up. I learned at Shipley how to feel confident in uncertain situations and aim to persevere even when times are hard. I am grateful for the lessons and skills I learned during my four years at Shipley. 

Tell us about a teacher at Shipley who played a key role in your growth as an individual. Can you share a specific instance where they influenced your personal or academic development?
One teacher who played a key role in my growth as an individual was Ms. Willing. I feel lucky to have taken two classes with Ms. Willing during my junior year, Biology and Environmental Science & Bioethics, and another during my senior year, Comparative Anatomy & Neuroscience Honors. Ms. Willing always challenged her students to think outside the box and look at things in a new light. I always loved going to her classes because she pushed me to grow as a learner. Every class she had a smile and a witty joke ready, which made class the most fun. I am grateful to Ms. Willing for being a great teacher and role model.

What extracurricular activities were you involved in at Shipley (sports, student government, clubs, service, awards, etc.)? Which Shipley activities were most impactful? Did you join similar activities in college?
Joining Shipley for Upper School, I was eager to get involved in as many things as possible. At Shipley, I was involved in Admissions, Theatre in all three divisions (Lower, Middle, and Upper), Positive Paws (Program Head), Shipley Sprouts, DECA (Chapter Head), and Action Research. I was also heavily involved in Student Government, serving as Head of Service Learning for my junior year and All-School Head of Student Life for my senior year. I really enjoyed being involved with planning things that would impact the student body and held a strong passion for volunteering and giving back. One of my favorite memories is starting the tradition and planning the first-ever Homecoming at Shipley.

In college, I participated in similar activities, focusing on connecting with others and giving back. At Penn, I was President of my tap dancing group, elected for two different Student Government Roles, gave back through Penn Special Olympics and the After School Arts Program, and led a division of the Penn Undergraduate Law Journal.  

Looking back, what do you think was the most valuable skill you developed at Shipley?
Looking back, I feel the most valuable skill I developed during my time at Shipley was the ability to advocate for myself. Advocating for yourself is extremely important in all facets of life, especially when you are young. I feel that this was something I really struggled with, especially during my freshman and sophomore years. I needed to learn how and when to ask for help and speak up on my behalf. Shipley instilled me with the confidence to do so, which has really helped me during my time in college and now in the early stages of my career.

What advice would you give to current or future Shipley students? 
I would advise current or future Shipley students to try everything and take advantage of the opportunities, both academic and fun, that are offered at Shipley and beyond. I think that being able to step out of your comfort zone and try something new is one of the best ways to grow as a person. There are so many opportunities in Upper School and beyond to join fun clubs, meet new people, or learn something new that I think can easily get lost in the focus of day-to-day things you have to do. I feel like these possibilities are what make life richer and more fun.