Overwhelmed by “Maycember”? 5 Ways to Get Through the End-of-School Chaos
Maycember survival tips from a seasoned veteran
Ah, Maycember. That glorious time when the universe decides to do all of the things, all at the same time, but without the glitz and glitter of the winter holidays. School concerts, end-of-year banquets, graduation parties to plan or attend, spirit days, field trips, final exams, and oh, by the way, you still have a job with deadlines and deliverables. Don’t forget Mother’s Day, Father’s Day, and Memorial Day events thrown in, just to keep the schedule spicy. It’s the end-of-school-year stretch where the schedule multiplies like Gremlins after a bubble bath, deadlines pile up, and your calendar is a pile of scribbles and overlapping events.
May isn’t about living your best life or being your best self. It is a marathon to be survived, running at a sprint pace. But here’s the thing: it doesn’t have to be overwhelming (at least, not every day). I know, because I have made it through the obstacle course, and come the end of my school-age parenting years. This year, we are navigating end-of-senior-year parties and celebrations, planning a graduation ceremony dinner and party, navigating the teen’s first experience with a college-level final exam while attending the last high school classes the next week (an adventure all in itself!), travel baseball practices and tournaments, end-of-year fundraisers and banquets, and squashing the senioritis. When my son was younger, we did all of the things, and for most of those years, I was managing it as a single mom. It’s a lot. It’s all of the chaos we were promised in motherhood, packed into one single month before the promise of lazier summer days.
So how did I survive? And more importantly, how can you survive, and maybe even have some fun along the way? If you’re the parent of a child still in elementary through high school, and maybe you’re also juggling the care of aging parents and working (or some mixture of these chaos gremlins), this article is for you. I’m going to keep this one relatively short because, well, it’s May - who has time to read a long article?
Survival tip #1 - Run your calendar before it runs you
If you’ve been reading along with Simple Systems for a while, you know that I am a HUGE fan of having a single, central digital calendar for taming the chaos bunnies. Everything goes into the calendar, even if you aren’t sure you can make it. Baseball practices and games, end-of-year volunteer group meetings and celebrations, school events - everything. Ideally, you also have your work schedule on your personal calendar. In my experience, this is the only way to actually see where the conflicts are at, and give you the option to prioritize what you do - and don’t! - commit to attending.
What to put on the calendar:
School events (performances, spirit days, early dismissals, exam days)
Sports/practices/games
Deadlines (forms, payments, teacher gifts, yearbook, etc.)
Work meetings
Personal care (hair and nail appointments, time out with girlfriends for a quick coffee to commiserate together)
Buffer time + drive time
Down time (seriously - if it isn’t on the calendar this month, it won’t happen)
The idea isn’t to DO all of the things, but rather to know exactly what the reality is - what you are being asked to do in a way that makes it highly visible, and allows you to choose which events are important to you and your family.
Survival tip #2 - Plan the plans
On the surface, May doesn’t look so bad, right? A few extra school events, maybe teacher gifts at the end of the year, and then it’s summer.
And then - BAM. Suddenly, you’re up to your eyeballs in running around, trying to figure out which child has which activity on a given day, and realizing you don’t have the snack/costume/dress outfit they need until the very last minute.
This is where survival tip #2 comes in - when you add plans to your central calendar, stop and take a minute to plan out everything you need to know and do to make that plan a reality. Ask yourself -
Who is going?
If you need to split parenting duties - who is taking on which event?
What needs to be prepared ahead of time, and does it require shopping? If it does, add the shopping trip and list to your calendar, with buffer time to move it when someone inevitably is sick that day and it has be re-planned.
What about meals that day? For example, an evening concert means either an early or late dinner - something in the crockpot, perhaps, for flexibility? This goes for daytime activities, too - if you are coming home tired from supervising field day, having dinner ready to go with minimal effort (or making it a pizza delivery night!) can save the day.
Once you have your plans planned, be sure to make them visible - add to the family digital calendar, or if your children and partner have their own digital calendars linked to the main family calendar, add all events to their calendars also. This is especially important for teens - gently pushing them to check their own calendar helps develop this skill early, and moves you away from being their personal assistant.
This brings me to survival tip #3…
Survival tip #3 - Delegate, delegate, delegate
I am going to say something radical and revolutionary - you do not have to do everything yourself. I repeat - not doing all of the things all by yourself does not make you a failure. It makes you human. Delegation isn’t a sign of weakness - it’s a sign that you are strong enough to ask for help and receive it.
If you have done step #1 and 2 (set up your central calendar and identified all of the tasks needed to make all events happen as smoothly as possible), then #3 is a breeze. Call a family meeting where everyone brings their calendars, and talk through the major events of the month. Yes, this is true even for the littles - they may not have their own calendars yet, but they can see their parents working together as a team, which is priceless.
At this meeting, go through each event, and delegate tasks in age-appropriate ways. Younger kids can pack bags, lay out clothes, help load the car, or help make lunches. Teens can organize their gear and outfits for events, and identify when they do need help (a ride to the mall for clothes shopping, or a night out bowling with friends to blow off steam after finals week). Parents can plan pickups, teacher gift shopping and drop-off, and meal coverage. Just as importantly, take a look at what can possibly be outsourced this month, if your budget allows. Would this be a good time to have a cleaning service clean the house once or twice? Switch to grocery delivery for a few weeks to save time in the schedule? Hire a babysitter for a much-needed date night somewhere in the chaos?
Be sure that as you delegate, everyone is clear about 1) who is doing the task, 2) what exactly needs to be done, and 3) when it needs to be done by.
If this set-up works for Maycember, consider making it a monthly family meeting to make your life easier throughout the year.
Survival tip #4 - Keep it simple
As a grizzled veteran of the Maycember wars, one thing I have noticed over the years is the “Pinterestification” of parenting. Why have dinner when you can turn it into a 3-course meal complete with dump trucks scooping up spaghetti off a foil-lined table? Teacher gifts aren’t just a gift card - no, they’re a handwoven basket containing handspun yarn from your own sheep. (you get the picture) And birthday parties must be insanely over the top, not just a nice dinner with cake and close friends and family at home. It’s all gotten a bit out of hand.
Under the barrage of videos and reels, and pictures showing these over-the-top approaches, it’s easy to think, “oh, that’s what I need to do too.” Maybe it looks fun, or maybe it seems everyone else around you is taking that approach, so you need to do the same thing.
If that’s your idea of fun, more power to you - I’m sure I’ll see your videos at some point. But if you’re a bit more down in the trenches (like me!) - give yourself permission to keep things simple this month. What does this look like?
Meals: repeat your greatest hits that you know how to make in your sleep. Use shortcuts like rotisserie chicken, bagged salad, and precut vegetables from the store.
Activities: pause the optional activities if you can. And say no to anything that adds weekly complexity. (confession: this year I thought it would be a good idea to sign up for golf lessons, since I have been wanting to learn how to play. Weekly lessons for 4 weeks, plus 2 Sunday mornings of actual play. Guess how many sessions I made? Yep - not a single one.)
Home projects: this is not the month to start your kitchen renovation. No projects that require three store runs and couples therapy. If your household is behind on needed maintenance tasks, hire a handyman service to knock off the list in one day.
Survival tip #5 - Have a system in place BEFORE Maycember
May happens every year, whether you like it or not. And every year is just as hard as the last year, if not more so. I was under the delusion that as my son turned into a teen, everything would calm down. Spoiler alert - it does not. Even though he can now drive himself to events as needed, there are still so many events to plan around (for example, baseball games mean planning picnic dinners at the field for the parents, along with pre-game, light dinners for my son).
While Maycember continues to be predictable chaos, how I respond to it has definitely changed over the years, in a good way. I have come to realize that by having household systems in place BEFORE May hits, I am better prepared to manage all of the events and tasks with relative calm.
The Maycember system is just an extension of the life system we’ve already discussed in previous articles. For me, my life system consists of:
a digital calendar (Google Calendar)
a shared digital task list (Google Tasks and AnyList)
a document scan process linked to event and task management (Ohai)
meal planning and shopping routines (AnyList)
support from family, friends, or paid help (Grandma!)
But what if it’s already May, and you don’t have a time machine lying around to go back to April and set this all up? It’s not too late! Gather up all of the activity paperwork and emails that are running your life, and call a family meeting to build your schedule together for the next few weeks. Go through the pile and add events to the calendar, decide who is doing what actions and when, and decide on a method for keeping track of it all. If that is too overwhelming, pick out just the top stressors that need planning, and work through those.
You don’t need perfect. You need a plan.
Hopefully these tips have sparked ideas on how to make your May easier. Remember: your goal isn’t perfection - it’s progress. And progress happens when you have a plan
If you want to do a deeper dive into the nitty-gritty of how to set up Simple Systems in your life, check out my free resources that help you plan your digital calendar system and then automate your Google calendar. I am adding new resources every week, so if you’re curious about how to set up Simple Systems in your life, please subscribe to my free newsletter - it will give you something to read poolside in June, when you have made it through the madness.
FAQs
FAQ: What is Maycember?
Maycember is that end-of-school-year stretch where everything happens at once—concerts, banquets, spirit days, field trips, finals, sports, graduation stuff—while your regular life (work deadlines, laundry, feeding people) continues to demand rights. It’s like December-level chaos… just with more carpool lines and fewer twinkle lights.
FAQ: How do I survive Maycember with a full-time job?
You survive Maycember with a full-time job by getting brutally realistic about time—and letting your calendar be the “source of truth.”A few sanity-savers:
Put every single event and deadline in one digital calendar (even the “maybe” ones).
Add drive time + buffer time like it’s an actual appointment (because it is).
Decide in advance what becomes “good enough” this month: easier meals, fewer extras, less volunteering, more delivery.
Have one weekly “Maycember planning meeting” (15 minutes counts) to look ahead and prevent surprise costume days from ruining your life.
The goal isn’t to do it all. The goal is to get through it without crying in the Target parking lot. (Or at least… not every week.)
FAQ: What should I put on my calendar during Maycember?
If it affects your time, your money, your transportation, or your sanity—it goes on the calendar. Start with:
School events (performances, early dismissals, exam days, spirit days)
Sports practices/games/tournaments
Deadlines (forms, payments, teacher gifts, yearbook, projects)
Work meetings + major work deadlines
Personal appointments (hair, nails, therapy, coffee with a friend who gets it)
Drive time + buffer time
Downtime (yes, schedule it—May will steal it otherwise)
Bonus move: add reminders before deadlines (ex: “Field trip form due” + “Print/sign form” two days earlier).
FAQ: How do I manage Maycember with teens?
Teens can handle more than we think… but they won’t magically do it without a system (and honestly, potentially a small bribe). Maycember with teens works best when you:
Make sure they have access to the shared family calendar (and yes, teach them to check it)
Put their responsibilities on the calendar too (study blocks, gear prep, rides they need)
Do a quick weekly check-in: “What’s coming up? What do you need from me? What can you handle?”
Push ownership in small ways: they track their own exam schedule, they pack their own gear, they tell you about conflicts before the night before
You’re not trying to be controlling. You’re trying to stop being surprised. And when they complain that you’re getting “too involved”, remind them that the more they engage with the process, the more space they will earn as they flex their adulting muscles.
FAQ: How do I keep up with school emails and forms?
School emails multiply like rabbits in May. The trick is to stop treating your inbox like a to-do list. Try this:
Pick one daily time to check school messages (morning or after dinner—whatever’s realistic)
When an email includes an action (form, money, signup), immediately do one of these:
Add the deadline to your calendar
Add a reminder to complete the task (with a realistic time block)
Create a simple “School” folder/label so you can find things fast
Keep one “Maycember landing zone” (a folder, a tray, a clipboard—anything) for paper forms so they don’t vanish into the backpack abyss
If you only do one thing: calendar the deadline the second you see it. Future you will feel personally blessed.
FAQ: What if I’m doing all the planning and it’s burning me out?
First: you’re not failing. You’re overloaded. There’s a difference.If you’re carrying the whole mental load, Maycember will absolutely light you on fire like the dumpster fire that May can be.
A few ways to put the fire out:
Call a family meeting (even 10 minutes) and assign who owns what: rides, forms, gifts, meals, gear, etc.
Delegate in age-appropriate ways (kids can pack, teens can prep, adults can coordinate)
Choose 1–2 things to outsource temporarily if you can (grocery delivery, cleaning help, meal kits, even just “pizza night” on repeat)
Give yourself permission to say: “We’re not doing extra this month.”
And if you need a script: “I can’t be the only one running this month. We’re going to split this up so everyone knows what they’re responsible for.”
