Just 100 Days Til Summer: The Beautifully Exhausting Truth About May
BY SUSAN LAIR, PHD - CONSULTANT, EXECUTIVE COACH
“May is the grand finale — part curtain call, part chaos, and all heart."
May: The Month with 100 Days
To most people, May means blooming flowers, smiling faces in caps and gowns, “Pomp and Circumstance” in the air, and the countdown to summer break. It’s field days, sack races, autographed yearbooks, end-of-year banquets, and students beaming with pride and possibility.
But to educators?
May is the longest short month of the year. Not 31 days; we know better. The academic fire dimmed the moment spring break ended. Now it’s testing season, a parade of performances, and a dash to wrap up curriculum before Memorial Day, when high schoolers vanish into their summer jobs as lifeguards, grocery store sackers, babysitters, and drive-thru attendants. By June, classrooms are boxed up, and in-service is underway.
It’s a month that feels like a hundred days, brimming with joy and chaos in equal measure.
And yet, May is magic.
But only because behind every finished course, photo op, and applause-filled moment is an educator fueled by experience, generosity, resistance to shallow change, caffeine, checklists, and sheer willpower.
No one survives it — let alone pulls it off — as educators do!
May's Greatest Hits: An Educator Remix
May isn’t a month — it’s a Broadway production directed by miracle workers. Teachers, staff, and administrators choreograph final assessments, emotional minefields, and dozens of events into one seamless show.
Field Day Throwdown
Sack races, egg tosses, tug-of-war, water balloons, forty-two parent volunteers, a faculty team wearing matching T-shirts, teachers refereeing with whistles, and administrators with walkie-talkies praying no one breaks an ankle or starts a fight that will end up with the valedictorian going before the Honor Council—What a Day, and schools across America do it every year!
Curtain Call Chaos
The spring play premieres the same week as awards night, senior sunset, and the championship game. Costumes go missing. The spotlight breaks. And thanks to one drama teacher with gaff tape—and Mrs. Hardwick, the steely, never-crack-a-smile AP Bio teacher whose secret weapon is four decades of quilt making, the show doesn’t just go on: it’s magnificent!
Yearbook Drop: Live from the Helicopter
Somewhere today, a faculty advisor is biting their nails. Still reeling from three months of copy edits, photo uploads, grammar checks, and topic vetting, the yearbook staff’s work culminates in a moment of pure drama, usually involving balloons and an assembly. Except this year, the yearbook staff secretly orchestrated an epic unveiling of the yearbook with the help of helicopter-dropped Ping-Pong balls announcing, "The Yearbooks Are Here!"
Mayfest and Mayhem
Every May, there’s face painting, a live petting zoo, student dancers, funnel cakes, forgotten sunscreen, and of course, a mariachi band that will accidentally arrive an hour early, rev up the loudspeakers, and start playing during the AP Physics Exam.
Transcript Tango
A seldom thanked registrar in the bowels of the administrative wing, deep in GPA decimals, triple-checking transcripts, courses, and honors designations while fielding the occasional panicked senior emails: "Wait, will the ‘F’ on my final keep me from walking?" "Will my college acceptance be in jeopardy over the 'D' Mr. Thompson gave me in economics?" Ah Yes. Yes, it might.
The Ballad of the Term Paper (Due After Prom)
Prom weekend fades, and on Monday morning, sleepy-eyed students stagger into class with crumpled dress shirts, half-eaten granola bars, and a thick stack of regret. Mrs. Aldriche's term paper was due today and waits for no one.
Semester Testin' Blues
Teachers move 500 desks to the gym. Two weeks of changed schedules. Can’t miss review sessions. Two two-hour semester exams a day. Endless tension. Students sit in long straight rows silently in a gym, pencils clicking, stomachs turning. A department of teachers proctoring in total silence, praying no one cheats or blanks on Hamlet. It’s a well-worn, outdated tradition, but it’s May.
Pomp and Circumstance (and Seating Charts from Hell)
Graduation: 150 students, each with a name that must be pronounced flawlessly — no do-overs, no phonetic mysteries. Diplomas double-checked, check. Last-minute name changes handled with grace and maybe a little sweat, check. Every diploma is perfectly printed and in alphabetical order, check. Every family accounted for, check. Every seat labeled, check. Every alum assigned to an advancement staff member, check. Are the faculty in their regalia, lined up according to years of service? Check. Every emergency plan rehearsed, check. Whoops! Seating charts rewritten moments before the doors open: Grandma needs wheelchair access! Check.
Graduation Rain Plan, Here we go again
Of course, we will have graduation outside, like the school has done for 75 years, even though it will rain. The outdoor ceremony will be called off again - thank you, thunderstorm. Chairs will be moved, programs reprinted, and the orchestra will now share a stage with the JV volleyball net. It's fine. Everything's fine. There will be a mad dash to find a microphone, 150 folding chairs, and air conditioning for 1000-plus family and friends.
The Speech No One Wants
The Head of School steps to the mic, ready to deliver 20 heartfelt minutes of wisdom. Parents shift. Grandma can’t see from Row J. Caps finally fly, and the Board Chair says, “Dr. Duffy, I loved your speech. You say the same thing every year, but it was great.” Next year, we're definitely getting a guest speaker!
Behind the Curtain: The Real Stars of May
For every magical May moment, there’s a behind-the-scenes team of exhausted, brilliant educators who make it all look effortless, holding it all together with binder clips, prayer, and unshakable grit.
The Teachers
In matching field day shirts (and possibly curlers), setting up cones and coolers before 6 a.m., and still grading essays by flashlight. One is managing graduation robes, another is editing programs, and all are juggling the final push to meet course deadlines, and there is a growing chorus of "Will this be on the exam?"
The Advisors & Counselors
They're checking in on sleep-deprived seniors who haven't eaten since prom dinner, meeting with second-grade teachers about a list of challenged readers, answering college deadline questions, scheduling makeups, calming nerves, and managing meltdowns from students who suddenly realize the term paper isn't optional even though they've been reminded every day since January, and it's due Monday. (Spoiler: Mrs. Aldriche never extends the deadline.)
The Parent Whisperers
You have some of these at your school, don’t you? Someone who can talk a person off a ledge and answer calls that begin with, "I just think it's a little unfair…" as parents argue that their child shouldn't have a test, a paper, and a dress rehearsal all in one week.
The Yearbook Sponsor
Running on adrenaline and nostalgia, this brave soul triple-checks photo captions, edits for grammar, and ensures no one gets "Most Likely to Be Indicted" in the senior superlatives. Then, they organize the big reveal — because yearbooks don't just arrive, they arrive triumphantly.
The Registrar
The unsung hero who checks every name, every grade, and every decimal point. Diplomas don't print themselves, and it turns out "Johnathan" and "Jonathan" are not interchangeable.
The Admin Team
They test microphones, rewrite seating charts when families triple in size, and move the ceremony indoors at the last minute without losing their minds. They hold it together with walkie-talkies, iced coffee, and good old-fashioned grit.
Educators don't just survive May: They Create Magic!
There’s a tired old insult: "Those who can't… teach."
As if real talent lies elsewhere — in boardrooms, or operating rooms, or hedge funds. As if educators landed in classrooms because they had no other options
What those critics don't understand is this:
Educators aren’t here because they can’t do anything else.
They’re here because they believe nothing else matters more!
Critics don’t see the sleepless nights — not from grading, but from worrying whether kids are okay, and whether parents will let them learn from struggle.
They don’t see the teacher fighting for a student in a team meeting.
They don’t see the math teacher creating a fourth way to explain parabolas.
Or the English teacher who cheers when a student finally understands a poem.
They’ve never felt the joy of watching a student speak their first sentence in Spanish, realize why cities rise near rivers, or suddenly connect the dots between war, power, and history.
They haven’t watched a nervous 6th grader transform into a confident graduate or had the quiet honor of walking beside them through the wins, losses, heartbreaks, and triumphs.
That’s why we do it.
That’s why we sprint through May, the month that breaks and remakes us.
Because we’re in it for the students, for the learning, for the moments that matter.
And after the last chair is folded, the gym is swept, the grades are submitted, and the transcripts are sent?
We’ll take one deep breath.
And then?
We’ll start planning for next year.
Because that’s what educators do!
Resources
May School Traditions
Pembroke Hill School (Kansas City, MO)
Pembroke Hill hosts a vibrant May Day celebration that immerses students in 16th-century English traditions. The event features flower gathering, feasting, the crowning of the May Queen, and traditional maypole dances performed by fifth graders and seniors. This longstanding tradition beautifully blends historical customs with school spirit.
Mary Institute and Saint Louis Country Day School (MICDS) – (St. Louis, MO)
Since 1912, MICDS has celebrated May Day with a festive gathering on Lilly’s Field. Students from various grades participate in maypole dances, and the event has been held at notable locations like Washington University’s Chancellor’s Garden and Forest Park’s Muny Opera stage before settling on campus.
Bryn Mawr College (Bryn Mawr, PA)
Bryn Mawr's May Day is a cherished tradition held on the Sunday after the last day of classes. The celebration includes a breakfast of strawberries and cream, a parade, traditional maypole dancing, and a feminist alternative called the "Mayhole." The event fosters a sense of community and marks the culmination of the academic year.
High Mowing School (Wilton, NH)
High Mowing School's May Day festival is a public event celebrating the arrival of spring. Activities include a pottery sale, musical performances, games for children, a maypole dance, and the May Day Play, where characters representing Winter and Spring engage in a theatrical battle, culminating in the crowning of the Spring King and Queen.
Girls Preparatory School (Chattanooga, TN)
At GPS, May Day is a pageant that combines Renaissance traditions with a debutante-style presentation. Seniors are introduced in colorful dresses, and a May Queen is crowned. The celebration includes barefoot dances by various grades, culminating in a maypole ceremony performed by sophomores for the Queen.
Visitation Academy of Frederick (Frederick, MD)
Visitation Academy's May Day, believed to have started in the 1920s, features a May Procession honoring the Blessed Virgin Mary. Girls dressed in white perform songs and prayers, and the student with the longest attendance crowns a statue of Mary with flowers, emphasizing the school's Catholic heritage. Waldorf Schools (Various Locations)
Waldorf School (various locations)
Waldorf schools across the country celebrate May Day with students preparing hand-woven baskets filled with spring flowers, which are then shared with the community. These celebrations often include maypole dances and other activities that honor the changing seasons and foster a connection with nature.
Graduation Traditions
Holy Trinity High School (Chicago, IL)
Holy Trinity High School's Robing Ceremony offers seniors the opportunity to honor a teacher, mentor, or coach who has played a pivotal role in their development. During the ceremony, the chosen individual robes the student, marking a significant milestone in the student's academic and personal growth.
Emma Willard School (Troy, NY)
Emma Willard's seniors participate in Revels, a theatrical production with roots dating back to 1915. This medieval-themed play, performed by the graduating class, is a highlight of the school's traditions, showcasing creativity and camaraderie.
Maryvale Preparatory School (Lutherville, MD)
At Maryvale, juniors receive their class rings during a special ceremony held on the Feast of the Immaculate Conception. A cherished tradition involves students having their rings "turned" several times, corresponding to their graduation year, symbolizing their bond to the class.
Holy Trinity High School (Chicago, IL)
Holy Trinity High School's Robing Ceremony offers seniors the opportunity to honor a teacher, mentor, or coach who has played a pivotal role in their development. During the ceremony, the chosen individual robes the student, marking a significant milestone in the student's academic and personal growth.