Kids Heading Back to School? Readers Share Their Best Advice to Help the Transition

Back-to-school season usually brings about a flood of emotions. Summer always seems like a milder, more relaxed version of real life, and sometimes, the anticipation of heading back to school and buckling down at work again just doesn’t seem very enticing. For parents sending their kids to school for the first time, this is even more complicated—a combination of nerves, anxiety, and pride is common among us first-timers. Then, there’s the whole school-in-the-midst-of-the-pandemic thing.

I know I’ve been anticipating sending my 5-year-old off to kindergarten since, basically, January, and I can’t believe the day is finally near. The entire last month was spent mentally struggling over how the heck I’m going to handle everything, with drop-offs and pick-ups at two different schools while managing my job, home, separation anxiety, and everything that’s involved in organizing the kids’ schedules and necessities. It all seems like way too much, and I found myself saying, “How do people do this?” over and over again.

But, there’s solace in the fact that parents everywhere do this—and successfully—all the time. We sometimes feel alone in our struggles and anxieties, but the truth is that we can learn so much from those who have gone before us. Hearing what works from other parents is one of the best ways to get new ideas, perspectives, and tips when you’re at a loss. So, as a mama struggling with the thought of her little one going to school for the first time, I turned to all of you. And boy, did you all come through.

Here are some of our favorite tips for preparing for school, organizing your family, and managing separation anxiety.


How to prepare for the first day

“Visualization truly helps! I spend time walking our boys through what the first day of school looks like and feels like. We talk about their teacher, where the classroom is, what they’ll eat their first day, and what they’ll do when they get there. It mentally prepares them so that when the day actually arrives, they feel comfortable and know exactly what to expect.” – Haley S.

I start talking to my kids about school a month before school actually starts. I read stories about going to school, buy a new lunchbox and new school-only shoes, and prep fun breakfasts together. I also promise not to bring little brother (who’s been getting all the attention) on the first day of school. Making school seem fun, special, and new helps.” Rachel G.

Start your morning routine a week before school actually starts. Getting up early and getting back into the routine is the hardest! Starting to wake up early and go to bed early a week before will help tremendously when school actually starts!” Jessica G.

“Getting back into the right bedtime routine at least a week before school starts, having conversations about expectations at drop-off (setting a certain number of hugs/kisses), sharing who will be there at pick-up, and explaining time away in a way they’ll understand all are helpful. I also recommend making sure you’re getting lots of quality time together so when it’s time to say goodbye, you don’t feel guilty and they don’t feel as anxious about leaving.– Cheyenne L.

Do a few trial runs! Give yourself a few days practicing getting out of the door on time—just do the commute and then check out a new park or run errands.” Em W.


siblings on first day of school

Source: @summerdavis via #sharetheeverymom


The best ways to keep everything organized during the week

Make lunches and prep bags the night before. Have your kids pick out their clothes before bed. If you can, prep breakfast the night before too, so you can have an easier morning and make it out the door on time.” – Emily M.

“Pack bags the night before for both adults and kids. Do laundry once mid-week (there are so many clothes once school begins). Sing songs together on the way to school. Lean into all of the feelings—whether you are a SAHM, working mom, single mom, it’s never easy on day one.C. N.

“Create menus with your child so that you’re not fighting over breakfast options and to ensure lunches get eaten!” Shari K.

I no longer try to get too creative with lunches for school. Early in the year, I was making something different every day for my 5-year-old. By the second half of the year, it was a Sunbutter sandwich every day, and she loved it! I try to give her a variety with sides and use a bento box like OmieBox so I don’t have to worry about baggies or containers.” – Kathy S. 

“Setting my son up for morning success is key. Sunday night, I fill special Monday-Friday drawers with his outfits for the week. We set up his toothbrush and toothpaste also. We make his breakfast accessible. He’s five, and if we walk through the routine together and have everything in place for him, he’s in the living room ready to go all on his own. It’s a game changer. It also makes him so proud to be ready by himself.” – Amanda C.

“I like to plan out my outfits on hangers for the whole week. I also try and choose a lunch for myself that can be made in a big batch and divided up for the week so it’s grab-and-go. I lay out my son’s outfits for the week, too. And program the coffeemaker—always program the coffeemaker.” Maria 

“Teach your kids to be self-sufficient and independent in the morning. As a single mom in a tiny apartment, we have to have a routine or else! The more we teach our kids to take responsibility for themselves, the easier mornings (and life) will be. My son started waking up to his own alarm, getting himself ready for school, making breakfast, and packing his own lunch in fourth grade. Now, he is in seventh grade and makes his own morning tea, too! It makes life so much easier.” Brittany

“1) Meal planning and prepping food is a life saver, especially for snacks and lunches. Have the kids get in on helping plan, and they will eat their food! 2) Have clear expectations for what’s supposed to happen when they arrive home from school, like have a snack, then do homework, or whatever it is. The first two weeks, they’ll be like wild horses trying to break free, but the routine will help in the long run. To keep organized, immediately mark the important dates when flyers and emails come home for events and deadlines. Otherwise, you’ll miss the yearbook order date or the ice cream party.” – Patty S.


little boy on first day of school

Source: @ojuspatel


How to manage the inevitable separation anxiety

“I heard some wonderful advice I plan on using with my preschooler: Draw a little heart on your hand, then one on your child’s hand. Tell them that every time they look at the heart, they will know their mama is thinking of them.Elizabeth

Llama Llama Misses Mama is a fantastic book to read for kids and parents dealing with separation anxiety when starting school for the first time.” – Samantha

“Here’s a tip for parents who travel for work. My daughter was extra anxious at school when I would travel. I started spending a little extra time to prepare with her before the trip. I would still plan and prep her meals, help pick out clothes, etc. We’d look up where I was going together, and I’d call right after she got home to hear about her day. As kids get to school age, I’ve learned including them in any changes to the routine is helpful!” – Patty S.

“Kissing hands always works for my oldest. I’m hoping it helps when I drop my youngest off for his first year of preschool!” – Mallory


This article was originally published in 2018 and has been updated for timeliness.

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