Toddler
Toddler

My Stella Bear is Growing Up: Navigating Preschool Drop-Offs & Big Girl Feelings (for all of us!)

My heart is just bursting bc my sweet Stella started preschool today, all by herself this year! It's so wild how fast they grow up, one minute they're tiny babies and the next they're walking into school like a big girl. I swear every milestone feels like a little piece of my heart goes with them, but also like a huge wave of pride, you know?

By Lo Beeston|December 29, 2025| 6 min read
My Stella Bear is Growing Up: Navigating Preschool Drop-Offs & Big Girl Feelings (for all of us!)

Key Takeaways

- Letting go is hard, but watching them grow is the best. - Siblings are the best support system, especially on big days. - It's okay for everyone to feel a little nervous or emotional. - Celebrating small victories makes a huge difference. - Every year brings new adventures and new memories.

My Stella Bear is Growing Up: Navigating Preschool Drop-Offs & Big Girl Feelings (for all of us!)

Oh my gosh you guys, my heart is just bursting bc my sweet Stella started preschool today, all by herself this year! I can’t even believe it. It feels like just yesterday I was holding her tiny hand and now she’s walking into school like a big girl. I swear every milestone feels like a little piece of my heart goes with them, but also like a huge wave of pride, you know? It's such a crazy mix of emotions and I'm just here feeling all of them.

Last year, she had her sissy Ozzy right there with her, holding her hand, navigating the newness together. They were like a little dynamic duo, always side-by-side. And honestly, it made drop-offs so much easier for me hahah. I knew they had each other. But this year? It’s just Stella, all on her own. And ngl, that hit me a little different. I knew it was coming, but knowing and feeling are two totally different things, right?

I woke up this morning with that familiar flutter in my stomach, the one you get on big days. It wasn’t just Stella who was nervous, it was me too! I was just praying she’d have a good day, that she’d make friends, that she wouldn’t miss us too much. I mean, my girls are my whole world, and sending them off into the world, even for a few hours, always feels like a big deal. I know you mamas out there totally get what I’m saying. It’s like you’re giving them wings but also wanting to keep them safe in your nest forever. Curse my freakin indecisiveness hahah.

The Morning Jitters & Sibling Love

Stella was definitely a little quiet this morning. She usually wakes up like a little ray of sunshine, ready to tell me all about her dreams, but today she was a bit more reserved. We talked about it while I was doing her hair, just me and her. I told her it was totally okay to feel a little nervous, that even grown-ups feel nervous sometimes when they start something new. I reminded her how brave she is, and how much fun she’s going to have. She just nodded, clutching her little backpack a bit tighter. My heart just ached for her, but I also knew she was ready for this.

And then, my sweet Ozzy stepped up. You guys, I swear these sisters are just the best. Ozzy, being the older sister (even if it’s just by a bit!), took Stella’s hand the moment we got to the school. She walked her right in, like a little protector. It was the sweetest thing I’ve ever seen. My eyes definitely welled up a bit. It’s moments like these that just melt your heart and make you so grateful for the family you’ve built. Tanner was there too, being his usual supportive self, giving Stella a big hug and telling her to have the best day. He’s always my rock, keeping me grounded when I’m getting all emotional. He just knows how to make everything feel okay.

Seeing Ozzy lead her in, it just made me feel so much better. It’s like even when they’re on their own, they’re never really alone. They always have each other, and that’s something I’ve always wanted for them. That bond is just everything. I love watching them grow together, learn together, and support each other. It’s truly one of the greatest joys of being a mom, seeing that sisterly love blossom.

The Bittersweet Drop-Off

The actual drop-off was quick, which is always a blessing, right? A quick hug, a kiss, and then she was off, disappearing into the classroom. I stood there for a second, just watching her go, and then took a deep breath. It’s always a little weird, that silence after they’re gone. The house feels so much emptier, even with Cherry still here. It’s like a piece of the energy just leaves with them. I immediately pulled out my phone to text Tanner, just a quick “she did so good :,)” bc I knew he’d be thinking about her too.

I remember last year, when both Stella and Ozzy were starting, I was a total mess. I think I cried on the way home hahah. It was their first real step into the world outside of our home, and it felt so monumental. This year, it’s a different kind of emotion. It’s less about the initial shock of them leaving, and more about watching them grow into their own little people, gaining independence. It’s beautiful, but it’s also a little sad, bc it means they don’t need you quite as much anymore. And I h8 that about myself hahah, but it’s true! I love being needed by my babies.

Reflecting on Milestones & Motherhood

Every milestone, big or small, feels like a little marker in time. From their first steps, to their first words, to their first day of school – each one is a reminder of how quickly time flies. It’s why I try so hard to soak up every single moment, even the chaotic ones. Bc one day, these little hands won’t be holding mine quite as tightly, and these little voices won’t be asking me a million questions a day. And while that thought makes me a little emotional, it also fills me with so much hope for their futures.

I’m so proud of Stella for being so brave today. She was nervous, but she faced it head-on, and that’s all you can ask for. It’s a huge lesson for me too, as a mom, to trust them, to give them space to grow, and to know that they are capable of so much more than we sometimes give them credit for. It’s about finding that balance between protecting them and letting them explore the world on their own terms. It’s a constant learning curve, motherhood, isn’t it? I feel like I’m always learning something new from my girls.

Looking Ahead: New Adventures & Memories

Now that the first day is done, I’m just so excited for her to tell me all about it when I pick her up. I can’t wait to hear about her new friends, what she learned, what she played with. Those little stories are my favorite. It’s like I get to experience a little piece of her day through her eyes. And I know she’s going to come home with a million art projects and stories, and I’m here for all of it. Our fridge is about to be covered in masterpieces, and I wouldn’t have it any other way.

Every year brings new adventures, new challenges, and new memories. And I’m just so grateful to be on this journey with my family. Tanner, Stella, Ozzy, and little Cherry – they are my everything. They make every day an adventure, and even the tough days are made better just by being with them. I wouldn’t trade it for the world. So here’s to Stella’s big girl year in preschool, and to all the mamas out there navigating these big, beautiful, sometimes overwhelming milestones. You’re doing amazing, and your kids are so lucky to have you. We got this! ❤