It’s September! If you aren’t already homeschooling because you live in a different part of the country, how’s it going? Are you having fun? Overwhelmed? Sleepy?
If you live in New York, you’re first day of school is any day now. I’m guessing you’re knee-deep in prep: sharpening pencils, printing schedules, or maybe just staring at the stack of curriculum you were planning on organizing by now. Personally? I’ve never been so behind while also somehow more ahead than ever. It’s a strange feeling.
And while the internet is overflowing with “First Day of School” content, I’m not going to hand you another list of themed crafts or elaborate photo ideas. Instead, I want to make a case for why the first day of school should be both special and mundane and why this involves waffles and pajamas at my house.
Why the first day should be the most chill…
Hi, if you’re new here: I’ve been homeschooling for ten years. My homeschool philosophy is simple. It’s not rooted in Charlotte Mason or Classical or Unschooling. It’s rooted in the fact that I’m a student of life, and I have a degree in Operations Management. Translation: sometimes the right thing is the minimum.
Traditional wisdom says that the first day of school should be “magical and memorable.” But here’s the reality: you may be excited to crack open that gorgeous curriculum. Your kids? They’d rather sleep in, watch cartoons, or play outside. Even my school-loving kids aren’t thrilled with the first day. Why? Because school is school, no matter how many gel pens and glitter glue you buy.
So why fight it?
Enter the waffles and pajamas…
After a decade of experimenting, here’s what I’ve learned about the first day of school:
- No one actually wants to do school. Not on day one. Not with new shoes or tech.
- Over-the-top unit studies backfire. If you turn your house into an Egyptian tomb and dress everyone like King Tut, nothing else you do all year will compare.
- Field trips aren’t better. Parks are full of homeschoolers celebrating their “freedom.” Translation: busy and chaotic.
- New homeschoolers beware because day one is prime time for nosy strangers asking “Why aren’t those kids in school?!” Take a couple days before putting yourself in that spotlight.
- Save your money. Life is expensive. Homeschooling can be expensive. Blow the budget on something really cool later, not balloon arches and chalkboard signs.
In our house, waffles are rare, which is why they are special. Pajamas are cozy. And when the “first day” looks more like a Saturday morning, than a school assembly, it reminds us that homeschooling is different.

Remember: You’re NOT doing “school at home”
You’re homeschooling. That means you have nothing to prove. You’re not locked into an 8-to-3 unless you want to be. Let the kids sleep in. Save the core four (math, English, history, science) for week two. Start with fun subjects. Do a fall-themed read aloud as a family. Bonus points of it’s spooky.
And if you must take first-day pictures? Skip the porch poses with the stats. Take pictures of whipped cream smiles and powdered sugar mustaches. That’s the memory worth keeping.
How do you celebrate your first day of school? Drop your tradition in the comments! I’d love to share ideas in a future round-up.



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