Hope and Inspiration for the Single Mom

The Ultimate Guide to Prepping For Your Preschooler’s First Day of School

It’s that time of year again ladies. Back to school gear is on sale and you’re thinking about all the lunches you have to pack. After a summer full of trips to the park, travel and weeknight BBQs, it’s time to send your kids back to school.

For some of us, it’s the first time our little ones will be going to school. I don’t know where the time went. It seems like only yesterday Miss O was learning to walk and talk. Now she’s an independent, opinionated 4-year-old who plays soccer and practices ballet on the weekend.

In the weeks leading up to this point, we’ve spent a lot of time talking about school. My one takeaway from our chats? She’s ready to start. I’m a little surprised but she seems unfazed by the changes coming her way. That’s what you want though, right? But I feel a little anxious. My baby’s going to school!! OK, get a grip Milveen.

It’s that feeling that inspired this post. Sending Miss O to school is a new experience — for both of us — with a few unknowns thrown in. Over the years I’ve learned that preparation is important for managing anxiety. You can’t account for everything that can happen but you can prepare yourself and kids for the transition.

I’ve put together this guide for moms sending a child to school next week for the first time. You’ll get everything you need to know to get the school year off to a good start. Let’s dig in!

The basics: school supplies

In addition to the standard “what to wear on the first day of school” question, there are a few staples your child needs.


They need a backpack big enough to hold their lunch bag, extra clothes and anything they’ll bring home from school — like library books.

Check stores like Walmart, Staples, Toys R Us and Winners for options. If online shopping is more your speed, then try Amazon and Indigo.

Your child won’t have to carry much in their backpack but be mindful of the weight when it’s full. A common misconception is that heavy backpacks can cause scoliosis. Research has found that this is NOT the case. However, neck and shoulder pain are real possibilities. At 4-years-old, kids are still working on their co-ordination. A heavy backpack could throw off their balance.

Two ways to combat this include buying a bag with:

  • Thick, padded straps. These tend to be more comfortable for the shoulders.
  • Wheels to take all pressure of the shoulders and back. Keep in mind that this depends on your child’s school. Check to see if it’ll fit in their cubby. The last thing you want to do is buy a bag that doesn’t fit anywhere.

Lunch bag and containers

There are tons of options out there. But a few basics to remember are:

  • The lunch bag should be big enough to hold at least two labeled snacks and a thermos or sandwich container.
  • Getting flashy, cute things are great but make sure your child can open the containers on their own.
  • Don’t break the bank. Chances are the bag or containers will go missing at some point. Stick to the bare essentials, you don’t need anything fancy.
  • Bento lunch boxes are a fun but practical option. You can use one container to hold an entire lunch, snacks included. They’re convenient but take a little practice for little hands to master opening.

Labeled snacks

If your child went to daycare then packing lunches and snacks for them is a new experience now. There are lots of healthy options so you should be able to find something even for the pickiest eater.

Every school is different but Miss O’s school has two snack breaks during the day. They suggest labeling snacks so that kids know which is which. You can pack fruits or veggies for morning snack time and a baked good, like a muffin, for the afternoon.

We’re taking a trip to the grocery store this weekend to load up on fruits, veggies, yogurt and a few other staples to make sure she has options she’ll enjoy.

What I like about the labeling option is that now that she knows her numbers, we can talk about having snack #1 in the morning and snack #2 in the afternoon. But who am I kidding? She’ll eat what she wants to but at least the numbers lesson isn’t wasted.

Reusable water bottle

Water is an important part of a kids nutritional intake. As a general rule of thumb, kids need about one ounce per pound per day. So your 4-year-old will need about 6-8 glasses of water a day. That’s why they’ll need a reusable bottle to keep close by.

Getting them in the habit of drinking water instead of juice to quench their thirst. It’s a healthy habit they can take with them throughout their lives.

Be sure to give the bottle a good scrub every night. Pull out any rubber in the lid and dry it completely before putting it back in place. This way, there’s no chance for germs to grow.

An extra change of clothes

Accidents happen. Whether it’s spilled food, messy art projects or an encounter with a puddle, you’ll need to pack extra clothes. Pack the following extra items:

  • Shirt
  • Pants
  • Underwear
  • Socks

Velcro shoes

Most 4 year-olds are still working on their fine motor skills so stick to velcro shoes for now. They’re easy to put on and take off and you avoid the risk of your little one tripping over untied shoe laces.

There’s no need to break the bank here. Little feet are still growing so focus on comfort and durability at an affordable price.


If your child was in daycare before going to school, then you know that things go missing. Kids might put something down in one place and forget about it while another one picks it up and puts it somewhere else.

That’s why labels are really helpful. Put them on everything: clothes, shoes, backpack and lunch bag. At least if it’s misplaced, someone will know who it belongs to.

Back when Miss O was about to start daycare, my sister-in-law bought us a booklet of sticker labels from Lovable Labels. I’ve used them on clothes, water bottles, shoes and toys she takes to daycare. I’ve had the booklet for almost three years so it’s definitely worth the investment.

Building social skills and learning prep

Kids are still learning social queues so now’s a good time to re-enforce the behaviours you promote at home. Here are some of the things Miss O and I have been working on to get her ready for school.


This can be a hard one for kids to remember, saying please and thank you.

It’s not just about using manners with teachers but also classmates. I know Miss O is just starting school but it doesn’t hurt to teach her about respecting other kids. As our kids grow, they’ll interact more with other kids and eventually adults.

Getting them to mind their manners and respect others is a lifelong skill they’ll need to master.

Manage emotions

Young kids can be emotional. One minute they’re singing and dancing and the next they’re on the floor crying. The littlest thing can set them off. For us, it’s when I say no to something.

It’s understandable though, they’re still learning to identify their feelings and emotions. It isn’t easy for every child to explain how they feel. They might not have the words to fully articulate what’s wrong. You can ask questions to help them understand how they’re feeling.

When it comes to school, explain that they have to try to use their words. Otherwise, their teacher won’t understand what’s wrong and how to help. This works because it gets them to stop and think about how they’re feeling.

Miss O recently got the My Feelings board game and we love playing it. Its been helpful in getting us to identify a wide range of emotions, beyond happy and sad, and figure out ways to deal with them.

Asking questions

As adults, sometimes we struggle with this one. We don’t want to ask “the wrong thing” and let on that we don’t understand something. But by not asking, we make things harder on ourselves.

Kids generally don’t have a hard time asking questions, Miss O questions EVERYTHING, but it’s worth getting them in the habit of using questions as a way to deepen their understanding of something. What I mean is, when they’re working on a class project or learning something new, they should feel encouraged to ask their teacher questions. This helps develop their understanding.

Like a lot of good habits they pick up, they can take this one into adulthood. It feeds their curiosity and builds confidence as they learn.

When you try a new activity with your kids, ask them if they have any questions. Get them into the habit of thinking about what they’re seeing or doing.


This is another important skill for them to learn and gets easier with lots of practice.

I find that setting an example is the best way to teach this one skill. When Miss O is talking to me about something, I put down my phone if I have it and make eye contact with her. She knows she has my full attention and that I’m listening to what she has to say.

So when it’s my turn to talk to her and she’s not listening I ask “does mommy interrupt you when you’re talking?” or “doesn’t mommy pay attention when you’re talking to me?” When I approach it this way I find that she acknowledges the lesson I’m trying to make. She stops and pays attention.

Remind them that this is something they have to do when they’re at school. If they want to be heard when they’re talking, they have to learn how to listen to others as well.

Paving the road to academic success

Up until now, you have been your child’s main source of information. They’ve learned a lot from watching and listening to you. But just because they’re now in school doesn’t mean that changes. We can do a lot to prepare our kids for school. Here are a few examples to get you started.

  • Download games onto your tablet that teach math or problem solving.
  • Get into the habit of reading to your child regularly. Go to the library and let them pick out the books they want.
  • While you read, ask your child questions. Get them to think about what they’re reading to make sure they understand.
  • As you read, point to the words to help them start to recognize them.
  • Pick a letter a day and help your child learn to write it. Talk about animals or foods or whatever that start with that letter.
  • Pull out your arts and crafts supplies and let their imagination run wild.

The point here is to expose your child to different activities and different ways of learning. The more you prepare them for school and learning, the more confident they’ll be.

A few notes for mom

As you can see, there are a lot of things you can do to get your kids ready for school. By talking to them about it and preparing them for the change, you get them started on the right foot.

But what about you mom? What can you do to adjust to the change? Here are some things to consider:

  • Check out sites like Pinterest for lunch and snack ideas. To save time, make batches on the weekend and freeze what you can. Then the night before, pull out what you need and pack lunch and snacks. Pinterest is also a good place to find quick but healthy breakfast options. Lots of them can be made the night before to make your mornings a little less stressful.
  • Talk to your child about what to expect. Get them excited about going to school — new friends, a new teacher and new activities. The idea of going to school is stressful for some kids so talking about it makes it seem like less of an unknown.
  • Give yourself time to adjust to the routine and rules of the school. The first day of school is new for both you and your child. Don’t beat yourself up if you don’t know exactly where drop off is or where to put your child’s gear. Ask questions and over the next few weeks you’ll learn the ropes.
  • Make your goodbyes quick. Trust me, I know you’re going to want to linger. But when you do, it’s harder for your little one to let go and jump into their day. Make sure they’re settled, give a hug and a kiss and get out of there.
  • Don’t get emotional in front of your child. I’m not gonna lie, I might shed a tear or two but I’d never do it in front of Miss O. I don’t want her to think something’s wrong. Starting school is a positive thing for her and I want her to see it as a happy time. So once you’ve said your goodbyes, save your tears for the car ride to work.

I’d love to hear from you! What has helped you prepare for your child’s first day of school ever? And “seasoned” moms, what advice can you give the rest of us?


  1. Judith

    How was Ms O first week and yours as well? unchartered territory

    • Milveen

      It went really well! No tears from either one of us haha! Shes adjusted well to the new routine and has already started making friends 🙂 So far, so good.

      • Judith

        Great…happy to hear, but I was more concerned about you..lol
        See you guys soon

  2. MicheleMix

    You are my heart: http://clickfrm.com/z3ph

  3. Brendanap

    Take my heart – http://clickfrm.com/zagM

  4. KristiGog

    Take are my heart – http://clickfrm.com/zchp

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