Sean Roling

University of Chicago Booth School of Business

Class: 2020

Hometown: Clinton, Iowa

Fun Fact About Yourself: I met my wife of nine years when she was unluckily sent as a foreign exchange student from her small town in Tlaxcala, Mexico to my small Iowa high school. We recently welcomed a baby boy, not long after I was accepted to business school – it’s been quite a year!

Undergraduate School and Major: United States Military Academy at West Point; B.S. Spanish and French

Most Recent Employer and Job Title: United States Army, Captain

What did your parents do for a living? My father is a self-employed semi-truck owner and operator, formerly contracted to a major moving company for 20 years, now to an enclosed-trailer car hauling company. My mother was a stay-at-home mom for my childhood; she has travelled with my father since my brother and I graduated high school.

What was the highest level of education achieved by your mother and your father? High school diploma

Which of your family members is your biggest inspiration? Why? Without a doubt, my father is my biggest inspiration. Merely striving to emulate his faith, work ethic, and selflessness has served to guide my career path thus far. Though his occupation meant regular periods away from the house during my childhood, he superhumanly crammed in invaluable interactions with my twin brother and I during his time at home, while managing to fix, build, or recreate just about anything that one could imagine.

He inspired intellectual curiosity by appreciating the uniqueness of a rock or a tree while on a hike with us, analyzing the craftsmanship of anything he thought well-built, and by daringly undertaking everything from car repair, to plumbing, to masonry, to myriad uncharacterizable tasks that required determined trial-and-error. The respect and gratitude of others toward him have served to inform my understanding of success more eloquently than any formal lessons. He and my mother instilled in my brother and me the value of hard work and honesty – embodying the maxim “If it is worth doing, it is worth doing right” – while offering unwavering support and encouragement to ensure that we both strove to realize whatever ambitions we might have.

What was the moment that led you to decide to pursue higher education? Honestly, I could not identify any one moment that led me to pursue higher education. I was lucky to be raised – both at home and at school – in an environment that not only valued learning, but which made me aware of and fortunate for the opportunities that lie ahead – should I choose to take advantage of them. While I never felt pressure to pursue a college degree, I was certainly encouraged to set goals and to strive to discover my full potential. Personally, the attacks of September 11, 2001 echoed in my mind throughout the remainder of high school and motivated me to pursue a military career, eventually leading to my application to West Point.

What was your biggest worry before going for your undergraduate degree? My biggest worry before my arrival to West Point was that I would not be able to pass the rigorous military, physical, and academic requirements. With no prior military experience and minimal interaction with members of the military before arriving, I really had no idea what I was getting myself into.

What was the most challenging part of getting your undergraduate degree? The requirements on West Point cadets are pretty significant. I probably averaged less than 5 hours of sleep on weeknights during my first couple of years there, though largely because I found myself genuinely interested in too many subjects and couldn’t stop reading and investigating more.

What didn’t your family understand about the higher education experience that you wish they would understand better? While the experiences of entering the military and attending college (in my case, a simultaneous undertaking) were unfamiliar to my family, I think they would be most surprised by my opinion that they prepared me well. A sense of personal responsibility and a desire to seek out challenges instead of evading them was more valuable than any academic preparation. Additionally, I think my mindset has changed significantly from when I left home to enter college – something they may or may not have noticed. Specifically, I find myself much less certain of the way things should be done (perhaps I didn’t learn what I was supposed to as a cadet…) and more critical of the information I take in.

What led you to pursue an MBA degree? I would not characterize myself as either business-savvy or particularly strong at math. Therefore, when considering graduate school, I prioritized quantitatively demanding MBA programs. I want to use the opportunity to address this perceived gap in my personal skillset and refine my understanding of global issues shaped by the decisions of private enterprise, markets, and human incentives. I hope to gain increased fluency in the activity of the private-sector and its interaction with the public sector, and to compare methodologies for analysis, problem solving, and management that I have refined during my military career with those experienced by my classmates. For the long term, I hope to acquire additional tools to be a more effective senior Army leader and to seek opportunities to empower private-sector solutions to social issues about which I am passionate.

How did you choose your MBA program? When looking at MBA programs, I needed one that was flexible enough to allow me to focus on academic expectations of the Army, as well as one that was willing to work within the constraints that the Army has established for active-duty students. Furthermore, I sought an institution that had a reputation for thorough analysis, encouragement of inquiry, and world-class faculty. Finally, I hoped to take the opportunity to be near my family in the Midwest after years of being stationed away from home and deployed overseas. Chicago-Booth not only met these criteria, but more than exceeded my expectations for professionalism during the application process and in their welcoming support to incoming students.

What was your biggest worry before starting your MBA? Just as when I was preparing to begin a new adventure as an undergraduate, I once again find myself excitedly facing the unknown. I have never been a civilian college student… nor worked in a non-government civilian environment since high school. I think that my biggest challenge will be balancing study with the new baby and everything there is to do in Chicago!

How were you able to finance your MBA as a first-generation student? I was extremely lucky to have been accepted into the Army’s Advanced Civil Schooling program, which sends active-duty Army officers to civilian graduate schools to pursue advanced degrees for specific follow-on assignments. Booth generously worked with me to provide a scholarship that allowed me to meet the tuition constraints necessary to the Army program.

What advice would you have for other first-generation college students? Value the life experience of the generations before you – non-academic lessons may prepare you better for success in college than you would expect. While going to college can set you apart, it should not be an end state but a catalyst for reaching your full potential; take advantage of the opportunity to be inquisitive and challenge assumptions!

What do you plan to pursue after graduation? I will remain on active duty and return to West Point as an instructor. I hope to positively influence the next generation of leaders by fostering critical thinking and encouraging informed decision-making through skills refined at Booth. Then, as a field grade officer in the Army, I hope to address operational and strategic issues faced by a military ever more affected by global markets and private incentives.