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Letter to My Daughter as She Starts Middle School

August 29, 2025 by Liz SanFilippo Hall

My darling daughter, 

Here we go again, hurtling toward another milestone: you’re in middle school! 

Throughout fifth grade, there was so much anticipation, so many questions, so many concerns (that you mostly shared between your friends) about what to expect. Your elementary school did a fabulous job of preparing you for this transition, but I wanted to emphasize, even though I’m sure you’re already sick and tired of hearing it from me, that I’m here for you. Always. 

I still remember how you, as a little girl, used to hide behind me when we went somewhere new. I still remember how you clutched onto the back of my pants, not wanting to let go. This persisted through preschool and kindergarten… and then the world flipped upside down because of Covid. You pivoted. We pivoted—as a family and how we approached life and learning. 

Letter to my daughter as she starts middle school

Here we are five years later, and I think both you and I can agree that you’ve come a long way. You no longer hide behind me, and you’ve found your voice. But that doesn’t change the fact that there will be times as you grow up, especially as middle school gets underway, when you won’t totally know how to handle something. 

Darling girl, I might be “old,” as you say, but I’ve lived it. Even if it may have been *ahem* a few decades ago, I have been there. In other words, I understand how middle school can be… challenging, socially and academically. 

But it’s also a time of discovery and learning who you are and who you want to be. I’ve talked to the moms of your besties, and we all agree that we’re glad you found some of your “people,” other girls you feel like you can be 100% yourself with—and that is HUGE. 

Then, when class schedules were released, and we realized all those besties weren’t in any of your classes… those big feelings surrounded us (because yes, I promise you, I felt them, too). It’s okay to feel those feelings. 

No matter how young (or old) you are, change can be hard. You won’t figure out everything right away, but I promise you, one of these days…

You’ll figure out how to open that finicky locker of yours.
You’ll know your schedule like you know the lyrics to your favorite Olivia Rodrigo songs.
You might lose some friends, but I promise you’ll make some new ones, too. 

In the process, you’ll grow up and learn a whole lot about yourself. 

Through all the ups and downs, please know this: I am here for you, whenever you need me, whether it be with a hug or a sounding board for whatever you want to share. 

I can just picture you rolling your eyes at me now. And that’s okay, too. Because no matter how old you are, you’ll always be my girl. 

Love you, always and forever,

Mom

***

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Filed Under: Family & Lifestyle, Life With Kids Tagged With: family, growing up, kids, lessons from little miss, letter to my kids, little miss, middle school, school

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authorlizsanfilippohall

Multi-genre author. 📚BECOMING CHARLOTTE CORDAY, a YA historical fantasy coming 4/27/2027 from Apprentice House Press

I’m trying something new... and something that a I’m trying something new... and something that all the “gurus” tell you not to do: I’m turning my blog into what blogs used to be. It will no longer be overly polished or put together. It will stop focusing on SEO. And it will be so much more vulnerable. More about why I’m making this latest pivot over on the blog, naturally. Www.OopsAndDaisies.com#WritingExperiment #AuthorsOfInsta
I laughed, I cried. This book was everything I nee I laughed, I cried. This book was everything I needed and more. Author @alison.espach took something heartbreaking and turned it into something beautiful about how we can embrace who we are. That’s all I’ll say so I don’t give anything away. But you know I can’t help but share a good quote (and there were so many!):“And it was perfect. It really was. But life is strange, always thinking this one thing is going to make you happy, because then you get it, and then maybe you’re not as happy as you imagined you would be, because every day is still just every day.” #AmReading #WomensFiction #5StarRead #BookRecommendation
My deadlines for two projects are approaching… My deadlines for two projects are approaching…But I also need to remind myself that time to create, play, and doodle is important, too. It’s what my family and I have decided is “productive rest.”#AmEditing #HistoricalFantasy #MyPlanner #Creativity
What filled my cup this week…. The views, waves, What filled my cup this week…. The views, waves, games, ice cream, writing… but mostly, time with my family.#SelfCare #Travel #Vacation #PureMichigan
Maybe I should have taken more photos… but once Maybe I should have taken more photos… but once we got to a certain point in the 1,000 piece puzzle it became WAY easier. For me, writing is the same way. Once you start seeing the pieces come together, it starts to feel familiar, and the end is there before you know it. To me, writing is just like putting together a puzzle. #MomLife #CreativeWriting #PuzzleAddict #LakeMichiganLife
When I don’t know what to write (or think for th When I don’t know what to write (or think for that matter)… I try journaling about it. So this week’s Substack, written while looking out over Lake Michigan, looks a little different. I’d love to hear what you think. #JournalWriting #AmDayDreaming #PureMichigan
While I’ve been up in Michigan, I’ve been thin While I’ve been up in Michigan, I’ve been thinking about all the different kinds of writing there are, and how energized I feel when I talk about writing with others. So, without further ado, here is the schedule for my next set of VIRTUAL writing workshops! August 26: Postcards and letters - reflective writing with letters we’ll never sendSeptember 16: Sensory writing - embrace the senses to amp up your writingOctober 14: Haunting flash fiction - seasonal and fun flash fictionNovember 18: Family Stories - journaling and oral historyDecember 9: Year in Review, Year Ahead - closing reflections and intentions. All classes include a writing lesson/craft discussion plus time for writing (and feedback on your writing if you want it). They will also be available individually later, if all 25 spots don’t fill up, but I’m giving first dibs to the people who want all 5!Link in my bio and story. #WritingWorkshop #CreativeWriting #FlashFiction
I suppose this is a good problem to have. 🤣🤣 I suppose this is a good problem to have. 🤣🤣🤣#AmWriting #HistoricalFiction #PureMichigan
We haven’t had as much time as we’d like outsi We haven’t had as much time as we’d like outside during this trip, but at least cloudy days like today - with a ton of wind - are beautiful.#MyMichigan #Inspiration #LifeWithKids
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