Transitioning George to School

I have hesitated writing about this topic because it is complicated, evolving, sensitive and very personal. But, here goes nothing…

As many of you know, George has been cared for by a nanny in our home since he was 3 months old. This arrangement worked for us on many levels and George thrived in this setting. The one tough period was when George’s nanny delivered her first child (in October of 2014) and went on maternity leave until January 2015. While our nanny was out on maternity leave, we went through a pretty difficult trial of temporary nannies and arrangements that would make your hair curl if I shared all the details. Once our nanny came back to work, everything was back to normal for all of us. Amen.

To make a very long story short (and to protect the privacy of our nanny) I’ll cut to the chase here – our nanny unexpectedly went into labor with her second child at the end of June and delivered her 2nd child at 29 weeks of pregnancy. Everyone involved in the situation was shocked. Fortunately, nanny and baby are doing well and both are thriving. Amen.

After much thought about how to care for George in our nanny’s absence, John and I decided that this was the best time to transition George into a new setting. Besides, with two kids under 8 months of age, it was unlikely that our nanny would be in a position to offer the level of care that George deserves and that we have come to expect. After hours of discussions, researching our options and touring prospective schools, we decided to enroll George into a Montessori school. Of course, we had to apply and then we waited on pins and needles to see if he would be accepted and if there was a spot for him. And, all this happened within a span of 10 days (partially while we were on vacation).

To our delight, George was accepted into our first choice and was offered a spot immediately. George began school (after we returned from vacation) on July 13th and I am thrilled to report that he is thriving in this new setting. In fact, today is George’s 1 month anniversary at school. We have survived 1 month of school, friends!

G school

But, it didn’t come easily or quickly. Here’s a brief summary of what the past month has looked like:

Week 1 – This was a good first week, although drop-offs were tough. G is very attached to me and there was a lot of crying (from both of us).

  • M – 1 hour at school together (Michelle and George)
  • T – 1 hour alone at school (George)
  • W – George stayed until 11:30 (alone)
  • T – George stayed until noon (alone)
  • F – George stayed through nap – 3:00 pm (alone)

Week 2 – After two days at home with teething issues, George had a great week. John dropped off George in the mornings and this seemed to help with the transition.

  • M – George was sick (had a low fever) and stayed home
  • T – George was better, but had to stay home (must be 24 hours symptom free to return to school)
  • W – George stayed until 4:30 (all day)
  • T – George stayed until 4:30 (all day)
  • F – George stayed until 3:30 (all day)

Week 3 – This was a great week. George stayed at school all day this week and did great at drop-offs. I traveled for 3 days this week and was nervous about everything. But, all was well.

  • M – George stayed until 4:35 (all day)
  • T – George stayed until 4:35 (all day)
  • W – George stayed until 5:00 (all day)
  • T – George stayed until 5:00 (all day)
  • F – George stayed until 4:35 (all day)

Week 4 – This was an even better week. I traveled for 2 days for work and everything flowed nicely with our school routine. George was teething again so he spent some time at home. There wasn’t crying at drop-offs.

  • M – George stayed until 4:35 (all day)
  • T – George stayed until 5:00 (all day) 
  • W – George stayed until 5:00 (all day) 
  • T – George stayed until 2:45 – went home sick
  • F – George was sick

Week 5 – Great week so far. No crying at drop-offs and big smiles/waving/blowing kisses from G when leaving the house in the morning. George is doing so well now. Our only issue at this point is nap time. George doesn’t usually nap right after lunch, so this has been an adjustment for everyone. He is sleeping better at night, so I am sure his total sleep situation is simply evening out.

  • M – George stayed until 4:35 (all day)
  • T – George stayed until 4:35 (all day)
  • W – George stayed until 4:35 (all day)

G in class

As you can see, things got better over time for all of us. If I had to offer a few tips about transitioning your little one into a new setting, here’s what I would suggest:

  • Have patience
  • Always say good-bye to your child (don’t sneak off)
  • Make it exciting (we bought George a back pack and he loves it)
  • Keep it positive (even when you want to die inside)
  • Get a Lovey (George didn’t use one before, but we got him a stuffed dog that can be pulled out of his backpack if he is having a hard time)
  • Allow for Extra Time/Snuggles at home
  • Arrange for a back-up babysitter/nanny for “sick days”


Now, here are a few general notes about the transition:

  • What we Love: Water Day (the kids play on a splash pad twice a week); making new friends,; great teachers; great curriculum; wonderful support staff; all food and snacks are included in tuition (including lunch).
  • What we Miss: Our Nanny (she is awesome); seeing George whenever I want; having lunch with George.
  • What we are excited about: All of the learning that George is doing; all of the friends George is making at school; Making friends with the parents of the kids in G’s class
  • What’s Changed: Naps; Morning Schedule (we don’t have leisurely mornings anymore); our grocery bill (I spend way less on food these days)
  • Challenges: Sick Days; Naps at School; Missing each other; Labeling everything that goes to school with George (clothes, toys, shoes, etc.)
  • Additional Benefits: Saving Money (G’s monthly tuition is less than half what we were paying our nanny per month); we truly savor the time we have together; nothing beats the hugs/kisses we get when we pick up G from school.


We know that George could have a set-back at any time and we are prepared for that. Even still, we are relishing in the new learning environment and love watching George grow and thrive in his new setting.


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