Sebastian Update: His First Two Weeks at Daycare

Today will be the two week mark of Sebastian being at daycare. As you can probably imagine it has been a tough couple of weeks. It was actually a lot more difficult than I ever imagined…on Sebastian. Of course Matt and I really miss him during the day, but he’s really been struggling with transitioning to his new routine. I’ve said a few times, Matt and I are very practical people. We understood that it would be tough for him, especially since we spent the whole first year together, but some days we wonder if it will ever start to get better.

Drop off

I should have asked other parents about drop-off. The first week I stuck around and talked to the teacher, that made it much harder on him. He thought we were there together. When I abruptly left without him, he was confused and upset. It’s tough to hear him so upset, but this week I got in and out of the classroom as quickly as possible.

ps. We also got him these shoes and they’ve been great for walking at school. Since he’s in the toddler’s room, he has to have hard bottom shoes. We LOVE Stride Rite’s Danny Shoes. So much support for Sebastian!


Sebastian takes a little bit of time to get used to things. I’m sure that is the same for most little kids. It’s now been a good six months since he slept in our room. He still whimpers when we put him down to bed at night in his crib. As some of you might remember, sleep training was a process for us. Eventually, it will be smooth sailing for him.

At school, he takes his nap on a cot next to all the other kids so it kind of forces him to fall asleep when it’s time. Since he was born, he was taking two naps per day. One at 10am and one at 3pm. It was almost like clockwork. He’d sleep anywhere from 1.5 hours to 2 hours. Now that he’s at school, he only has one nap a day and it’s been tough for him to learn how to sleep by himself in the school room. Most days he takes anywhere from an hour to 1.5 hour nap. This leaves him exhausted when he gets home. He’s so tired and fatigued. From the moment we pick him up he starts rubbing his eyes.

Getting Updates

One thing we’ve really enjoyed is getting updates from school. They’ve actually made this entire process really easy. We love the teachers, the policies and constant updates! Sebastian gets a report card that is sent to us at the end of each day. We get an email with what happened (what he ate, how long he napped, how many diapers, etc), pictures and videos of him that day. We never expected that but it allows us to be with him when we are away. There is an app, Tadpoles, that they use so as the teachers upload throughout the day, we can see pictures of him in class. It’s a great way to keep the parents involved.

Things we didn’t think about…

One of the things Matt and I didn’t think about when we began daycare was the preparation and amount of time it can take to get him ready to go to school in the morning. Getting him dressed is usually no problem at all. I will typically pick out his outfit the night before. It’s preparing his lunch every morning that takes some time. There are labels we have to fill out each day to put on his food and drink containers. Right now we’re using these food containers. Not the biggest fan of our drink containers (they can’t have bottles). If you have any recommendations, we’d love to hear. Oh yes, we also bought this warm food container. It was one of the first things that teacher told us to get. Keeps his warm food, warm! Forgot about those things. 🙂

Usually, we will give him leftovers from dinner the night before along with his fruit squeeze and crackers. He has to have two bottles for milk and one for water. I put it all in his backpack and we are off. Fortunately, the daycare is fairly close so it makes it easy to go get him when we need to. Our morning schedule with Sebastian tends to look like this…


  • 7:30- Sebastian wakes up, drinks a bottle of milk, gets his diaper changed, plays with his toys and we drink a lot of coffee
  • 8:00- Make Sebastian’s breakfast (usually eggs & avocado & raisin bread), wash out his lunch containers, prepare his lunch, and we all eat breakfast together
  • 8:45- Get Sebastian cleaned-up, change his diaper, put on his OOTD, and get ready to leave.
  • 9:15- Drop off Sebastian and we are off
  • 4-5pm- We will go pick up Sebastian and
  • 5:30- Start making dinner
  • 6:00- Dinner
  • 6:30 Bath Time
  • 7:30- Milk, Book and Bedtime

The best part of our day is wrapping up work (at least until he goes to bed) and heading over to pick him up. It is the ultimate anticipation and we both end up trying to get to the door first. So childish 🙂 Once he sees us, he starts crying. It’s adorable. We grab his things and head home for dinner. The teachers are telling us he is doing great now and improving every day as far as getting into the routine. This has been a great transition for us all and especially Sebastian. We are so happy with the decision but we still miss the little nugget every day!

Now for the fun stuff…

Matt + Olivia

Well, first and foremost, we’ve brought back Wine Wednesdays. Matt and I met at a Tapas Restaurant, we spent most of our weekends when living out in San Francisco driving out to Napa Valley. We love wine! Last Friday, my amazing friend Kristen watched Sebastian so we could meet up with an old friend, it was good to get out as a couple.

Since the first week was really only three days, we got a small taste of getting organized and working ahead of schedule. Although Sebastian is gone for 6-8 hours, we have to be very mindful of every minute. Time flies. This week we had a great schedule and on task. On the work front, we are doing well.

We’ve been able to spend more time with Sebastian in the morning. We all have breakfast together, we get ready together and drop him off at daycare. After picking up Sebastian we’ve been really good about spending time with him. However the last few nights we’ve both been on the computer editing photos while he’s awake, so we’re still trying to get better. We’ve also been able to have dinner together every night. I’ve really enjoyed this part of this entire change. Matt and I both come from families where we sat down for dinner together, every night. There’s something special about ending the day together. Around that time is typically when Sebastian is falling off the rails, because he’s so tired. We power through dinner, clean, clean and clean some more (how do kids get so messy?!). Next we bathe him(every other night at least), wrestle him to put on a diaper and pajamas and then off to bed!

I’m convinced that part of Sebastian being in daycare has cut down on us cleaning the entire house daily. Matt and I both have a small dose of OCD, so having a semi-clean apartment to wake up to every day has been good for everyone. Living in NYC, a small mess feels like a huge mess in our tiny homes!

Just wanted to share a little update, because for a brief moment things felt a little broken, happy to report that we’re moving in the right direction. Thanks for all your comments. You all are really are the best!

xo, Olivia

Sebastian's Style


  1. sarah wrote:

    For my 15 month old, we use the advent straw cups for water after searching a long time for one that could be easily completely taken apart to avoid mold. We use take and toss straw and sippy cups for milk. Easy to clean and my little guy loves it because it’s like a grown up cup…. but has learned how to pull out the straws and take off the top, so I only give it to him with supervision (as compared to the Advent one that goes room to room with us).
    I hope the transition keeps getting easier faster! For us, getting used to the naps was the hump we had to get over. Good luck!

    Both links are below.

    Posted 1.12.18 · Reply
    • olivia wrote:

      Thank you so much!! I just ordered the Avent cups!

      Yea, naps seem to be the biggest hump. The teacher just wrote me and said that he had a great nap today. I’m so proud of him. <3

      Kids are the best. Thanks for writing!

      xo, Olivia

      Posted 1.12.18 · Reply
  2. Heather wrote:

    Hey Olivia,

    Loved this post! Question, as I am trying to figure out the same thing for my 12 month old daughter. I’m not a blogger, but I do have a small at home business, so I wondering what the reason was for full time daycare versus a nanny or something like that at your home? Where you finding it too hard to get work done with him there or were you looking for him to have more socialization?

    Loving your blog and hoping Sebastian transitions into his new schedule quickly!


    Posted 1.12.18 · Reply
    • olivia wrote:

      Hi Heather, that’s a great question! I should include in the post. Living in NYC, we have a 1,000 sq foot apartment. That doesn’t give us a lot of space for another person in our home when we’re trying to have meetings, shoot content and work on our other business ideas.

      As much as I’d love the 1:1 for Sebastian, we wanted him to learn from other children. He really enjoys being around other children. It’s been tough for him, but next month I bet he’ll love it!

      xo, Olivia

      Posted 1.12.18 · Reply
  3. Meriem wrote:

    Hi Olivia! Little Amelia is starting daycare next month so I’m really loving your blogs. Thanks! When we visited her daycare, they recommended this website
    It might make the labeling part of your day easier 😉

    Posted 1.12.18 · Reply
    • olivia wrote:

      Thank you, Meriem!!! I will look at the site right now!! Good luck. Amelia is going to do great! Sebastian didn’t cry on Friday, but he did learn how to fake cry, so he fake cried today when we picked him up. Gotta love kids!!

      xo, Olivia

      Posted 1.15.18 · Reply
  4. Maria Rivera wrote:

    Stride shoes are the best for kids. They give them support and are well made. My 5 year old has worn them since his first walking shoes. We do other fun and trendy shoes for the weekend, but for day to day wear, we always go to Stride Rite. They have a wash and play or wash and go shoe line that you can obviously wash in the washing machine. My boy started school (vpk) the first time this year and he wears his on most days. Enjoy Sebastian, and the school routine will get easier I promise!

    Posted 1.12.18 · Reply
    • olivia wrote:

      Thank you! Yes, we LOVE Stride Rites. That’s amazing to hear about your son. We’ve been hearing that from a lot of other parents. We will need to get our hands on those wash and go shoes. I might need your help with tough stains in clothes, that’s my new obstacle as a new mom!

      Thank you for the support!!

      xo, Olivia

      Posted 1.15.18 · Reply

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