Winter's Transition to Preschool


Back in November, just after Winter’s 3rd birthday, our nanny gave us two-day notice that she was quitting because she got another job. TWO DAYS! Perry and I looked at each other in a panic because here we were with a newborn, both trying to work from home and Winter’s world had completely been flipped upside down.

After getting over the shock that we lost our childcare, we had to regroup and do so rather quickly. We got so lucky that our neighborhood Montessori preschool had an opening and we started Winter that following week.


I didn’t want to write about how the transition was going back then, because it was rough and we were just surviving. Winter went from having three adults at home with her (Me, Perry and the Nanny), to having two parents who were beyond sleep-deprived, a new baby brother and no nanny.

I was so anxious to drop Winter off that first day. If you know her, she has these epic breath holding spells and because she had seemed so emotional and stressed as it was, I was super scared she was going to lose her mind at preschool and have episode after episode. The director of her school knew our apprehensions and did so well setting our hearts at ease by texting us updates a few times each day for the first few weeks.


Winter, despite my initial anxieties, did and is still doing absolutely great. That first day, she hugged my leg and said “Okay bye Mommy.” Not one tear! It was evident that she wanted to go to school and our sweet little shy Winter was suddenly blossoming in front of our very eyes.

The teachers said that Winter is pretty slow to warm up to others, quiet and well-behaved. She’s one of those kids that watches from the periphery, taking everything in before deciding if she wants to be involved. But with each week, her teachers say that she has opened up a little more and has quite a lot to say when they are working with her one-on-one.


The hardest part for Winter (and for us!) was the napping transition. She went from napping two to three hours a day to not being able to fall asleep during rest time. Friday nights continue to be really hard because she is just exhausted from the week. I think there was one night she asked to go to bed at six! Now, Winter doesn’t nap except the very rare occasion on the weekends and a few cat naps at school. But to be honest, Winter seems so much happier now that she is in school that it makes up for the fact that she is no longer napping.


Winter is blossoming in front of our eyes. At breakfast this morning, Perry and I were talking about how she seems more like a little girl and less like a toddler. She has learned so much since starting preschool and we don’t for a moment regret it. It was really a blessing in disguise that our nanny quit. Winter is constantly coming home with new songs, new poems she recites, shows off her math skills by counting to 20, tells us all kinds of new information about bugs, weather, music and more. And while she is away learning who she is, Perry and I are able to get work done and spend some quality time with Lennon.

I was so hesitant to make this leap to preschool. It had always been just Perry and me taking care of her with occasional help from the nanny. I am so glad that I was able to push through my hesitations with sending her to school. Winter really is thriving and I wouldn’t change our decision one bit.


When did your little ones start preschool?

Matching Mommy and Me Jean Jackets by Ingrid and Isabel

Photography by Kyla Fear