May Day

by John Boozang, Director of College Counseling, Wilbraham & Monson Academy

 

For centuries, May 1, known as “May Day,” has marked the midpoint between the spring equinox and the summer solstice. Rooted in the ancient Roman Floralia, a six-day festival to honor the goddess of flowers, as well as in medieval pagan celebrations throughout Europe, May Day festivals welcomed the arrival of spring. Far more recently, May Day has taken on new meaning in the United States, particularly for first-year college and university applicants. May1 is National Decision Day, the date for impending high school graduates to submit their enrollment deposit to the college or university of their choice.

For many high school seniors, the final step in their college search process—deciding where to enroll—can be the most challenging. Some may envy those admitted as Early Decision applicants, thereby spared the burden of weighing options, given the binding nature of Early Decision agreements. The notion of choice, in what is arguably the first major decision in their lives, can be overwhelming at times but also empowering.

Throughout my experience as a boarding school college counselor, my favorite time of year is when seniors return from March break with stories of home and updates on college decisions. It’s a mix of good news, bad news, and surprises. I have learned the therapeutic value of active listening as students share their news and associated emotions, especially when denied admission. For some, this may be the first time they have been able to talk about the decisions, their disappointment, and feelings of rejection. I always remind them of a tenet of our school’s college counseling program, coined by one of my first mentors, who advised students: “To the best of your ability, completely personalize each aspect of your college search and application process, and then, to the extent possible, completely depersonalize the admission decision.” Obviously, this is easier said than done.

People need time to process disappointment, and well-intentioned platitudes often fall short. “It wasn’t meant to be” or “When God closes a door, He opens a window,” provide little comfort to a student only recently denied admission to their “dream school.” What is effective is the comfort of family and friends, the familiarity of the mundane, and the routines and busyness that seem to define high school life.

I’m reminded of a bitter cold Saturday afternoon in March 1983, when I entered our kitchen with my two best friends to find three pieces of mail addressed to me. Each thin envelope, sent from one of my top five schools, would remain unopened as a rejection letter, or a “bullet,” as we called them. Offers of admission arrived in oversized packets. “That’s a bummer–let’s get some pizza,” my buddy Steve offered as my dad slipped me a twenty.

I often share this with students to emphasize that they will not only survive but thrive in not enrolling at a certain school or schools. I’m grateful to have been denied because it led me to a college that fit me well, perhaps better than the others, and where I made it the “right” school in how I invested in the many aspects of college life—academics, extracurriculars, friendships, parties, opportunities, and challenges included—that enriched and defined my undergraduate experience and the many years since. I have no doubt that another good-fit school could have provided for a similarly rich and fulfilling experience, but I wouldn’t change a thing.

At our school, the college counseling program begins in the spring of 10th Grade with Sophomore Seminar, a weekly class that includes an overview of the college planning process, access to our college search software, and most importantly, an introduction to the lifelong skill of self-reflection. Like most high schools, from day one of the college planning process, we emphasize the paramount importance of fit as the guiding compass. As they prioritize fit-driven search criteria in Junior Seminar, students develop an initial list of prospective colleges and universities that align with their unique interests, preferences, aspirations, and abilities. Ongoing research and sustained self-reflection, aided by college websites, virtual and live campus tours, and frequent college counselor meetings, contribute to a nearly final list of ten or so schools by the start of senior year. The list must be balanced in terms of realistic chances of admission, including one or two Likely-Admit schools, three or four Target schools, and three or four Reach schools. Although chances of admission vary, it is understood each school would be a good fit for the student.

By April 1, most schools will have released admission decisions, leaving students with a month to decide where to deposit and subsequently enroll. Regardless of a student’s level of excitement or disappointment, the following tips can help make the best decision about a school that suits them.


Ownership of the Process

In Sophomore Seminar, we pitch college planning as a treasure hunt, and each student as a ship captain searching for their bounty: a rich, fun, and fulfilling undergraduate experience at a college that fits them well. It’s understood that the quantity of treasure is directly proportional to the quality of fit. Admittedly, this analogy is met with some eye rolls and chuckles, but the point is clear enough: College can and should be among the more formative experiences in life.

During Junior Seminar, we adopt a more sophisticated model, with the student as CEO of their college search company, their parents as members of the board of trustees, and their college counselor as board chair. Given our school’s curriculum, which includes yearlong and elective economics courses, this model resonates with many of our students. They understand the value of preparation, partnership, action steps, and fully exploring their options in each phase of the process.


Does the Fit Still Fit?

When a student has had ample time to process their admission results and options, we discuss their current perception of a good fit to determine if it has changed since they applied. Every so often, a student will share an experience, insight, or even an epiphany that changes their notion of fit. Interest in a different major, school size, or location, or an unexpected family situation are just a few of the factors that can redefine what fits.


Visit Anew

A campus visit, including an information session and a tour, is perhaps the most effective way for students to gauge their initial level of interest. For many, however, these visits occur as early as junior year or during the summer months when campus life is not fully represented. In addition, the experience is markedly different as a prospective applicant compared to an admitted student.

I encourage all students and families to participate in admitted student days, which provide a more in-depth understanding of a school’s academic, extracurricular, and residential life programs, its culture, facilities, traditions, and other areas of interest. Interacting with current students and asking probing questions can also be enlightening.


Financial Fit

A benefit of Regular Decision and Early Action admission offers is the ability to compare the net cost of attendance at respective schools. For many students and families, this can be a significant factor in determining the best fit. Parents should consider and discuss this early in the search process. It’s worth noting that college financial aid offices do consider appeals for additional need-based or merit aid.

Students are also encouraged to explore scholarship opportunities. Each high school’s guidance or college counseling office maintains a current list of scholarships, complete with descriptions, qualifications, and links to applications.


Trust Your Gut

For many students, the ultimate choice of where to deposit is an easy one. For others, there may be no clear favorite, even after attending campus admitted student days, engaging in further self-reflection, comparing academic programs, campus culture, location, affordability, and other practical considerations, and discussing options with parents and counselors. Generating pros and cons lists, weighted according to fit criteria, can be helpful; however, some students still remain undecided. In these situations, I have found the following approaches can be helpful:

  • Remind the student that each school remains a good-fit option, so they can’t make a poor choice. Any of the schools has the potential to be equally formative and fulfilling.
  • Ask the student to think about which school best aligns with their values, interests, preferences, and aspirations.
  • If a student favors one school more than the other(s), but can’t articulate why, this may be intuition at work and should be considered.
  • The gut-check test: Ask the student to name one school as “heads” and the other as “tails,” and then flip a coin. Reveal which school was identified and immediately ask the student if they felt a rising or sinking feeling.
  • “1% Decisions”: Explain that some choices in life can be described as one-percenters, whereby someone may favor one only marginally more than the other.

Regardless of the decision complexity, it’s important for students to trust that they have personalized each phase and every aspect of their choice. For all students, enrolling at any college or university requires a leap of faith despite the unknowns, the what-ifs, and curiosity about other options. Most will find that any reservations about their college choice will dissipate as they explore all their college has to offer, and in the enduring friendships they are bound to find.

 

Artificial Intelligence »

« Education Guide 2025-2026

 

 

 

Related Articles

This Greenwich Home is Packed with Plenty of Style and Some Serious Marble Moments

One designer’s journey through setbacks, self-discovery and the beauty of starting fresh

Where to Eat in Greenwich & Stamford This Fall: New Cafés, Mediterranean Mezze, Dumplings & More

Whether you’re after comfort food, global flavors or a sweet treat, these new arrivals serve up the season’s best—and won’t break the bank