How preparing for preschool with my fourth child taught me that every milestone hits differently
The little red bag that has been hanging on a hook in our front hall for a couple of weeks now looks so very tiny. The bag belongs to my three-year-old (we’ll call her Joy), who started preschool for the first time just three days ago. You’d think by now—with three older sisters who’ve walked this path before—I’d have this whole preschool transition thing figured out. But as I stare at that tiny bag, my heart feels just as full and conflicted as it did ten years ago when I sent my eldest daughter off for her first day.
The Fourth Time Isn’t Always the Charm
When people hear I’m sending my fourth child to preschool, they assume I’m an expert by now. “Oh, you must be a pro at this!” they say with knowing smiles. The truth is, every child’s preschool journey feels like uncharted territory, even when you’ve navigated these waters before. And, let’s face it, we were in the middle of a pandemic the last time I did this. It’s been a minute, and my heart and mind are struggling to keep up with all the changes.
Joy is sandwiched between her three older sisters—ages 13, 10, and 8—and her 10-month-old baby sister. She occupies this unique middle space in our family, where she’s simultaneously the little one who still needs mommy and the big sister who proudly helps with diaper changes (though her version of “helping” often involves loudly announcing “STINKY BABY!” to anyone within a three-block radius). Watching her prepare for preschool has reminded me that each child brings their own personality, fears, and excitement to major milestones.
The Fourth Time Isn’t Always the Charm
When people hear I’m sending my fourth child to preschool, they assume I’m an expert by now. “Oh, you must be a pro at this!” they say with knowing smiles. The truth is, every child’s preschool journey feels like uncharted territory, even when you’ve navigated these waters before.
Joy is sandwiched between her three older sisters—ages 13, 10, and 8—and her 10-month-old baby sister. She occupies this unique middle space in our family, where she’s simultaneously the little one who still needs mommy and the big sister who proudly helps with diaper changes (though her version of “helping” often involves loudly announcing “STINKY BABY!” to anyone within a three-block radius). Watching her prepare for preschool has reminded me that each child brings their own personality, fears, and excitement to major milestones.
The Weight of Being Number Four
There’s something bittersweet about preparing your fourth child for preschool. With my first daughter, everything was monumental. I documented every moment, from the preschool tour to picking out the snacks that she was to take for her class on that first day. By child number two, I was slightly more relaxed but still deeply invested in every detail. Child three? Well, she missed preschool thanks to COVID, and went straight to pre-K when she was four, which was a whole other situation full of all kinds of unknown variables that we eventually overcame.
But with Joy, I find myself caught between the wisdom of experience and an unexpected tenderness. Maybe it’s because I know how quickly these moments pass, or perhaps it’s because with a baby at home, I’m acutely aware of how precious these early childhood years truly are.
Preschool Readiness in a House Full of Sisters
Joy’s preschool preparation has been unlike her sisters’ experiences. She’s grown up in a house where homework happens at the kitchen table, where older siblings practice spelling words aloud, and where backpacks and school supplies are part of the daily landscape. In many ways, she’s been ready for school since she could walk, mimicking her sisters’ routines and begging to do “homework” of her own (which usually involves scribbling on important documents and declaring herself “the smartest”).
She’s also mastered the art of preschool-level negotiation. When I told her she’d need to use the potty at school like a big girl, she countered with, “But what if I’m too busy playing to remember?” When I explained the drop off process, she said “But mama I want you to get me out of the car. I want to hug you and you kiss my cheek.” You’re seriously breaking my mom heart over here, kid.
Yet she’s also had the luxury of extended babyhood. With three older sisters eager to help and entertain her, and a new baby who’s claimed much of my attention, Joy has lived in this sweet spot of being both independent and cherished. The question isn’t whether she’s ready for preschool—it’s whether I’m ready to let her grow up.
The Unique Challenges of Multiple Children
Sending Joy to preschool while managing the needs of four other children presents logistical challenges I didn’t face with my first. The baby’s nap schedule must align with preschool pickup. The older girls’ after-school activities need to work around Joy’s new routine. Even something as simple as attending new student/parent orientation becomes challenging when you’re juggling multiple schedules while also trying to give your three-year-old all the attention she needs and deserves.
But there are lots of unexpected benefits too. Joy’s older sisters have become her biggest cheerleaders, sharing stories about their own school experiences and helping her practice writing her name. They’ve created a support system I couldn’t have provided alone, and their excitement for her milestone has infected our entire household. Though I could do without my 8-year-old’s helpful suggestion that Joy should “just pretend to be sick if she doesn’t want to go,” or my 13-year-old’s detailed, graphic lecture about why she needs to use hand sanitizer, wash her hands and NEVER put her hands in her mouth (let’s just say there were lots of references to “disgusting vomit” in that lecture). Thanks for the pep talk, girls.
The Guilt and Joy of Preschool Transitions
As a mother of five, I carry a unique type of guilt about Joy starting preschool. Up until April, I wasn’t even planning on sending her to school this year. I work part time, she doesn’t have to go to day care, and as a benefit of having three older sisters she already knows so many of the things that kids are taught in preschool. However, another side effect of being the “baby” of three older sisters (even though we now have an actual baby) is that Joy is used to getting her way ALL. THE. TIME. with her big sisters. She is used to being the boss. I realized that she really needs the socialization that preschool brings, and that she needs to realize that she can’t be the boss.
Even with this realization and knowing intrinsically that we are doing the right thing by sending her to school, I still can’t help but sometimes wonder if it’s too soon. With the baby requiring so much attention, I sometimes wonder if I’m using preschool as a solution to my divided attention rather than a natural next step in her development. Other times, I feel guilty for being a little bit excited about having just one kiddo at home a few hours a week.
The truth is, it’s both and neither. Joy needs the social interaction, the structured learning, and the independence that preschool provides. She needs to be seen as Joy, not just as someone’s little sister. This will be a good experience for her, no matter how much mom guilt I might feel from time to time.
What Preschool Means for Our Family Dynamic
Joy starting preschool will shift our family dynamic in ways both subtle and profound. For the first time in almost a year I’ll have just one child at home for two and a half hours twice a week. The house will be quieter, but also lonelier. My 10-month-old will miss the constant entertainment that her big sister provides during that time.
Most importantly, Joy will begin developing her own identity outside our family unit. She’ll make friends who don’t know her as the fourth sister. She’ll have experiences that are entirely her own, stories to tell us rather than stories we’ve shared.
Embracing the Beautiful Complexity
As I write Joy’s name in permanent marker inside her jacket and pack her school snack, I’m reminded that parenting is never a straight line, regardless of how many times you’ve walked the path. Each child deserves their own journey, their own celebration of milestones, their own moment in the spotlight.
With Joy’s first day of school already under her belt, I hope that this week goes just as smoothly. And even though she’s already made it through day one, I know that each day could bring water works– more likely for me than for her at this point. The tears aren’t just because she’s growing up, but because in a house full of children, these individual moments of transition are precious gifts. They remind us that despite the beautiful chaos of a large family, each child’s story matters deeply and deserves to be honored fully.
The little red bag with her school logo by the door isn’t just a school supply—it’s a symbol of Joy’s next adventure, and I can hardly wait to watch her soar.