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How to breeze through the diaper-free preschool transition with ease

Updated: Dec 28, 2023

Prepping for the preschool transition? Here's a simple list to help potty training toddlers transition to preschool or daycare.


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If I had to focus on one takeaway for helping toddlers adjust to preschool, it would be this...


The magic is in the transitions.

Meaning how you prepare your child can set them up for an easier preschool transition, especially diaper-free. The small stuff matters.


I love a good list, especially for anything school-related. So here's a few essentials to have in place for the preschool transition — simple ideas that I've seen help in big ways as a potty training consultant. Prep your toddler for a smoother transition to preschool!



preschool transition tips
simple tips to help the preschool transition



Feeling connected to you while being apart can make all the difference for your toddler — feeling brave to talk to a new friend, try a school snack, and even pee in an unfamiliar potty.


1. Prepare your toddler for what school will look like — a children's book about starting school helps with the preschool transition.


My new favorite book pick for introducing school to toddlers is I Am Ready for School. It's part of a children's empowerment book series that I love.



The retro-style illustrations are colorful and playful, and the core message is meaningful and positive.


Toddlers can feel it when big changes are coming.


You want to talk about the change coming up with the transition to preschool, and this is a great book to introduce the idea. Even sharing that sometimes we feel shy in new situations.


2. Set up a transitional object for being apart from you (and feeling brave to use the preschool potty).


A transitional object is a tool that's especially helpful for potty training toddlers who may be hesitant to use the school potty apart from parents. Find something small and pocket-size, like a simple stone (or a frog worry stone), that can be a transfer of security from where the child is having potty wins (at home) to where you want your child to have potty wins (at school).


Or a special bracelet can be worn on school days as a way to connect to you, where you charge it up with your love to help your toddler feel brave when you're apart. ❤️



transitional objects for preschool transition
A bracelet or a pocket-size stone can be transitional objects.

3. Pack supplies in a pouch, including extras — just in case.


Sometimes even the solidly potty-trained toddlers struggle with accidents when starting preschool and transitioning to so many changes — new classroom, new teacher, new routine. It's smart to set up a wet/dry pouch with extra supplies. This waterproof wet bag comes in a set and is made from recycled plastic.


What if the accidents don't shake out after your child's initial transition to preschool?

Our Daycare/Preschool Blueprint shares solutions to fix issues at preschool, depending on the potty training problem — whether you're hearing back about too many accidents or your child is withholding pee for a long time that's sparking concern.


If your toddler is new to wearing underwear, you'll want to prepare for that transition BEFORE preschool starts. How to add in underwear for your toddler? What should that prep look like?


Ideally, a slow-roll transition.


  • That means adding a little time in underwear each day over the course of several days to be sure that the barrier of underwear doesn't turn into immediate accidents.

  • Start with an hour in the afternoon where you add in the underwear (with your child wearing underwear, only).

  • Going well? See what a few hours in underwear (no pants!) looks like for your toddler.

  • Then practice the double-layer of underwear with pants/shorts over the underwear. Can your toddler push both layers down? If not make it a game and practice as the afternoon activity (you can use a stopwatch, turn on fun music for your child, make it like a challenge.)

  • As you see your child take on the barrier of underwear (block 4 of Oh Crap Potty Training), keep slowly adding in more time in more clothes! First the underwear and then the double-barrier of undies with pants.


Build in the transition to toddler underwear, slowly!


I love cloth training pants as an easy-to-push-down option for toddlers (and these cloth training undies also absorb dribbles with the extra fabric in the front panel.)




For more tips on toddler underwear and practicing the pants, check out my underwear and pants guide.


4. Pack a water bottle for preschool.


Hydration is important for the pee and the poop. A personal water bottle is also a helpful way to get a sense of how much your child is drinking at school while you're apart.


  • Does the water bottle come back full?

  • Are you hearing that your child is hardly peeing at school?

  • Does your toddler need to urgently pee at pickup?


I'd ask the teacher if they refill water bottles in the day if you're unsure how much water intake is happening. Our go-to water bottles have been the Klean Kanteen stainless steel water bottles, and they come in some fun patterns for kids, too.



And you can pack some love into your child's lunch. I like lunchboxes with compartments that separate out the foods (and toddlers tend to prefer that as well.) This leak-proof silicone lunch container is easy to open and comes with different sweet illustrations.


A few favorite snacks that made it into the lunchbox above:

Note: Most of our pantry staples and snacks I find on Thrive. If you're new to Thrive, you can use my link to get 40% off your first order if you'd like to try it out (and get lunch and snack supplies shipped to your door!).


Here's more on foods that help your toddler poop easier (mild toddler constipation is common when there's a big transition like preschool). I also share more food inspiration as you're packing lunches on my Pinterest board if you'd like to follow along.


So truly, the magic is in the transitions, and the magic is in you, the parents.


You've got all the magic your toddler needs to work through this big preschool transition. 🍎



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