(Inside: Freshman year of high school is a milestone transition for both the moms and the kids. Moms, this is how you mentally prepare for freshman year of high school.)
I watched from the driver’s seat as my oldest son shut the passenger door and walk towards the high school entrance for freshman orientation.
My eyes shut and opened, and the scene changed.
Instead, I saw a small blond-headed kindergartner proudly sporting his Captain America backpack turn to make sure he caught my eye. He lingered, smiled, and waved.
Then I blinked again and was back to watching a 6’1’’ freshman’s back getting smaller.
It felt strange.

I’d never not gone with him to see him meet his teachers, find his classroom(s), and unpack his school supplies in his locker.
From kindergarten to 8th grade, bustling around the school with other parents and their students is the only norm I knew.
As I observed my son gather with his peers outside the main door, unexpected big emotions swirled. But how exactly did I feel? It was hard to pinpoint: Disappointment that I can’t go with him? Pride that he’s getting independent? Disbelief that I’m old enough to have a high school kid?
My muddled feelings, though, pointed me to this truth: my role as a parent just changed.
I just took a new place in his journey – a few steps back.
I know these next four years will be important years with big life lessons. To grow and mature he needs to learn to navigate his path with independence. But still, I catch my breath at this change.
Because I know people are going to hold his heart who don’t deserve it.
Yes, he will make solid life-long friends, but these years are when his peers are figuring themselves out too. So, sometimes he’ll be overlooked or mistreated or not cherished the way I’d like to see, and it’s all a part of growing up. He’ll learn the value of true friendships and how to navigate the social scene.
However, as he maneuvers through peer relationships, even though my role has changed, he’ll still need me. And I’ll be waiting – simply a few steps back.
I also know expectations are higher.
Grades count. ACT scores stick. Teams start cutting. Clubs do adult things like build robots and give speeches. In it all, he’ll start figuring out his skill-set and interests and direction. Then, everyone will be asking where he wants to go to college and what are his post-graduation plans – he’s going to experience a new kind of pressure.
However, as he maneuvers through learning about himself and finding direction, even though my role has changed, he’ll still need me. And I’ll be waiting – simply a few steps back.
Responsibilities grow.
From getting a job to learning to drive, he learns to manage more. His schedule becomes his charge as the school staff and coaches and bosses communicate with him and not me. In these years, he’ll get a glimpse of adulting.
However, as he learns to get organized and manage heavier responsibilities, even though my role has changed, he’ll still need me. And I’ll be waiting – simply a few steps back.
There will be joy and struggle.
He’ll find success in unexpected ways, and his confidence will grow. But also, he’ll mess up and be disappointed. And sometimes, I will draw the line on important things and say “no” to remind him who he is – a good kid growing into a good man. I will also get to cheer him on and tell him how he makes me so proud.
As he goes through the highs and lows of the teen years, even though my role has changed, he’ll still need me. And I’ll be waiting – simply a few steps back.
Just like in elementary school and in middle school, the homework assignments and practices and homecomings and evenings-with-friends-over will all tick by so fast.
I’ll blink, and he’ll be in a cap and gown receiving his diploma.
But, I’m not there yet, I’m sitting here in the car at the start of this journey. My hands maneuvered the steering wheel out of the drop-off zone. Even though I began inching away, a piece of my heart stayed. And a mourning for that little boy and his Captain America backpack flashed through me.
Yet, I also felt something else: gratitude I get to be with him during these next four impactful years – what a gift!
And it’s okay that I’m a few steps back.

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Read the full Help Your Kid Thrive in School Series
As a high school teacher for over two decades, I love, love, love watching kids learn. It’s okay if there are struggles in their educational journey. Not just okay – normal, even. We just keep stressing the importance of education and giving them the tools of success. And then we encourage our kids and love them well.
I hope you enjoy these articles.
Help Your Kid Thrive in School Series
ENCOURAGEMENT FOR PARENTS
Parents, Help Your Kids Thrive in School By Asking These 4 Questions
Why I’m Not Freaking Out that My Struggling Reader Has Low Reading Scores
A Mom’s 1st Day of School Wishes
Moms, You’ll Better Enjoy the End of the School Year Remembering THIS
GETTING ORGANIZED
Kid’s Morning Routine Checklist: Get Your Kids Out the Door Happy and On-Time
BOOKLISTS
146+ Best Chapter Books for Tweens that Will Also Build Character
Compelling Books that High Schoolers Will Want to Read


Cheryl is a mom of 3 boys, wife, speaker, high school teacher, and author of Empowered Moms & Kids. She has a Master’s degree in Educational Leadership and is passionate about learning and teaching. On www.empoweredmomsandkids.com you’ll find inspiration and encouragement for moms raising tweens and/or teens. Read more in the “about” section of this page.