Seek Out Mentorship Between the Lines
By TMP 43rd Editorial Board
In a 1996 episode of Seinfeld, George and Jerry, two of the hit sitcom’s main characters, attempt to become “mentors” in their respective professions as a ploy to advance their careers. The pair winds up accidentally switching their mentorship materials, resulting in a standup comedian delivering a risk management presentation at a comedy club and a corporate employee reading hackish jokes in a risk management meeting. While this comeuppance appears far-fetched, it highlights the dangers of treating the mentor-protegé connection as purely pragmatic, a valuable lesson for Milton students in 2025.
When alumni speak about Milton, they commonly reference the school’s sense of community and the relationships they built here; Dr. Callen’s favorite word comes up frequently in conversation about our core values as a school. Ultimately, the relationships we form here are what make this place special.
Most of these friendships are born out of structured groupings; hours working together on extracurricular projects and minutes between shared classes make for convenient connection. Often, these instances of forced proximity blossom into profound connections. Even so, the friendships we maintain untethered to any current class, club, or affinity spaces—the ones that drive us out of our way— are among the most beautiful and lasting relationships we can pursue at this age.
The same paradigm holds true for mentorship. Mentorship has become almost institutionalized at Milton, with overwhelming messaging directed at upperclassmen that they are to act as role models to freshmen and sophomores within their student organizations. This attitude can, in our view, be beneficial. Still, we propose that there exists another level of cross-grade connection that seems to have slipped through the cracks of our communal ambitions. We’ve been trained well in academic and extracurricular mentorship, but we’ve let the toolkit of emotional mentorship fall by the wayside. We need to remember that mentorship isn’t just about sharing Honors Bio study hacks or training next year’s club heads. More than educational tools, the people around us both inadvertently and undeniably shape our responses to events impacting us.
This kind of mentorship requires upperclassmen to go beyond built-in shared spaces and embrace the emotional value of a reciprocal relationship. Mentees can receive feedback and advice passed through the sieves of experience, and mentors should, through sharing their outlooks, refine their own worldviews. Absent this kind of vulnerable, two-way exchange, the relationship between mentors and mentees risks slipping into idolization, wherein implicit reverence creates emotional distance that prevents bonding.
Transitions, NSO, and freshman year in general mold students around an ideal of what community-building should look like at Milton: showing up for your class. We have a plethora of SAA events that act as rites of passage for freshmen: Quadival, Glow Dance, and the Class IV Dance, for instance. The burst of loosely structured events allows for diverse freshmen to mingle with each other as long as they show up. However, behaviors that promote cross-class friendships beyond extracurricular activities remain few and far between aside from orientation.
Intra-grade relationships manifest at every stage of our high-school journeys, from freshmen’s jostling in Project Adventure to seniors’ hashing out spring break plans. By senior year, these connections will have largely moved beyond school-structured shared spaces and into the realm of authentic endeavors, but by staying within the comfort of our own social textiles, and shirking genuine, reciprocal friendships with different-aged peers, we reduce the number of meaningful connections we get to make. The burden of reaching out and stringing new threads falls upon all students, but especially upon upperclassmen, who, whether we believe it or not, have had our capacity for emotional mentorship forged in the fires of adolescence. It’s time to use it.