Full disclosure: Not my favorite holiday

I know people who passionately love Halloween. They go all out on costumes and makeup. They host parties. I am both so happy for them AND this has never been my posture toward the holiday. Could it be residual religious trauma from a pretty intensely evangelical upbringing? Maybe. But regardless of why, it’s just never really been my jam. It gets a “meh” from me. That said, I won’t yuck your yum, and I’m all about letting kids have fun, but my strategy is get through it with minimal stress and take fun pictures to prove we made the memories. See, kids? Your childhood was fun! :)

Identifying Halloween pain points and finding solutions

Halloween-related challenges fall into four buckets for me (but let me know if I’ve missed any of yours):

Costumes

I’m not particularly crafty or skilled in the sewing department, nor am I flush with time to attempt it. Thus, I’m a fan of kids taking ownership of making their costumes, store bought costumes, or outsourcing the work to people who can take it on. Think grandma, Etsy makers, or even finding local help by posting on community social media pages.
Talk to your kids early and often about what they’re thinking they’d like their costumes to be. Involve them in evaluating good choices (ex. can you comfortably wear this costume trick-or-treating? Will people know who you are?) making lists of supplies they need, and even giving them deadlines for when they have to make their final decisions. Young kids are notorious for changing their minds last minute and may not have the executive functioning skills yet to plan ahead and commit to an idea. Thus I highly recommend picking up some second-hand costumes at consignment shops or as hand-me-downs and giving them a choice between options you CAN make happen (ex. You can be Mario like we planned - OR I found this really cool pirate costume. Those are the best choices we have for now, buddy) .
If you feel “meh” (like me) about dressing up, then either 1) don’t do it and don’t feel bad, 2) go with a super low-lift costume (I’m a busy parent, a sports fan - or throw on a witch’s hat and call it a night), or 3) throw together a fast punny one to show you understood the assignment but you’re just not taking it that seriously. I am a long-standing fan of the punny costume, and I am not ashamed.
Here are some store bought/pieced together costumes:

Here are some homemade wonders:

Magical unicorn, a birdhouse (with a perch - hehe), Piggy from Elephant and Piggy books by Mo Willems, and a dolphin trainer.

And some punny/lazy ones:

Microsoft (wearing microfiber shirt) Outlook (binoculars) E-MALE (I know, it’s ridiculous). His attachments (see all the file types). Yes we are nerds. And yes, this picture was included in an MSNBC online article for nerdy costumes. We know no shame. :). Then we have “it’s raining cats and dogs,” a smartie pants, Dominoes pizza, and finally, I’m “a fork in the road” and my husband is a tired VT Hokie fan. Feels right.

Day of mechanics: Dinner, homework, candy consumption, and the aftermath

This is where Halloween can sneakily cause the most stress — taking the plans and making them happen in the short window after school and before bedtime. Woof. Take a deep breath.

Homework. Ideally your kids’ teachers aren’t assigning homework due November 1, but it can’t hurt to be proactive and anticipate this pain point. Check the newsletters, have your big kids check their learning management system (like Canvas, Schoology, Blackboard, or Google Classroom) to see what’s coming up. Encourage your kids to advocate for themselves and check with teachers early in the week to see what can be knocked out ahead of time so you’re not trying to do math worksheets while the doorbell is ringing every two minutes.
Dinner. Might I suggest leftovers, takeout, or delivery? Halloween is not the night to test a new recipe or cook something elaborate. Throw some soup in the crockpot, heat up some nuggets and mac n cheese, reheat a casserole, or order pizza. Think quick, kid friendly, and easy.
Candy. I like to let my kids enjoy some of their haul, but I don’t let it turn into a free-for-all. Too much sugar plus adrenaline makes bedtime a nightmare. I let them have 3-5 pieces while they’re trick-or-treating and then we save the rest for another day.
The aftermath. Ideally, you’re reading this on a year when trick-or-treating occurs on a Friday or Saturday. Or your school system geniusly set November 1 as a teacher workday. :) If this isn’t the case, consider allowing your kids to sleep in a little and start their school day an hour later. Or if this isn’t possible, anticipate that they will be exhausted by the afternoon of November 1 (hint: another easy night of dinners, please). You may find yourself needing to say no to things that next afternoon/evening (extra activities, invitations, commitments) so that you can say yes to Halloween fun without the stress hangover.

Trick or treating vs. manning the door

My kids are nearing the end of the trick-or-treating with parents stage, so I want to be with them as long as they want me. That said, I am also looking forward to sitting at the end of our long driveway and greeting neighborhood kids instead of running around. If you want to both roam the neighborhood and hand out candy, here are a few ideas:

Divide and conquer: one adult takes the kids, one stays home. Switch halfway if you want both experiences.
Invite neighbors, friends, or grandparents to join in so someone can keep the home base running.
If everyone’s going out, turn off your porch light so trick-or-treaters aren’t left frustrated.
Put out a candy bowl with a note. Fair warning: sometimes a kid takes it all (womp womp), but many years it works just fine.

And if you are reading this early enough in the season, start stockpiling candy early when it’s on sale to save you money and avoid the last minute rush to the grocery store.

Safety

Halloween fun is better when everyone makes it home safe. Before the night kicks off, talk through the ground rules:

Manners matter—please and thank you always — and only take a piece or two — whatever the giver instructs you.
Stick to sidewalks, avoid running through yards, and look both ways before crossing.
Only approach well-lit houses and never go inside.
Don’t tell strangers your name or where you live.
No opened candy goes in the mouth.

And visibility is everything: glow sticks, flashlights, neon vests, reflective tape—basically, if your kid looks like a human highlighter, you’re doing it right. Bonus: easier to spot them when they inevitably dart ahead with friends.

Final thoughts

Halloween can be as complicated or as simple as you make it. For some, it’s the holiday highlight of the year. For others (like me), it’s more about survival and memory-making than Pinterest-perfect experiences. Either way, identifying your pain points early and smoothing out solutions makes the whole night a lot more enjoyable.

If you’re spooked by Halloween prep, I’m your ghoul (hardy har har). Let me help you out.

Are you overwhelmed at the thought of sourcing Halloween candy, costumes, and safety gear? Have you committed to hosting a spooky party and you’re in over your head? Do you need someone to help you think through logistics in October. At Laura Kassner Consulting, our suite of Life Wife services reduce your mental load and stress. In the big things and the little things, we are here to support you. Shoot me an email or set up a time to connect and I’ll keep you from feeling batty.

My Halloween cheatcode