Parenting a High School Freshman May Be the Hardest Parenting Yet

Before I became a parent, I assumed parenting was hard. 

Then I had my first baby and quickly realized that parenting is way harder than I ever could have imagined.

When my baby became a toddler with his own big personality, an inhuman-like ability to slither like a snake out of my arms when he didn’t want to be carried, and a deep commitment to throwing massive tantrums, I realized that parenting had somehow become even more challenging.

I’m in the hardest phase of parenting with a high school son. (Twenty20 @testingtelli)

Parenting a high schooler is the hardest phase yet

Fast forward to today and I find myself facing the hardest phase yet of parenting: parenting a high schooler. With just a short bit of time so far under his belt as a high school freshman, I find myself more confused than ever when it comes to how to parent my son. 

When do I step in and communicate with his teachers? 

How much do I remind him and check up on him about his school work and home work, especially during these times of partial remote learning?

When do I loop in the administration if there are bigger concerns?

What ARE bigger concerns at this age?

When do I get involved?

When do I keep quiet and shrink into the background?

Today the finish line of his childhood looms larger than ever in the distance. Next year he can drive a car. In two years we start looking at colleges. In three years he’ll be in his final year of high school. 

Just like that — these days will be gone.

The pressure of finishing high school looms large

Sometimes the pressure of that looming finish line is overwhelming, knocking the breath right out of my lungs. We have just a short time to hold on to him tightly and enjoy these final years while at the same time stepping back from him and letting him make his own decisions and fail on his own.

Parenting a high schooler seems to be a never-ending cycle of missteps and course corrections, a constant stream of muttering lessons to ourselves:

“Oops I stepped in too far. I should have let him handle this.

“Oops, I should have jumped in sooner. This was too much for him to handle on his own.”

For over 14 years I have known that every stage of parenting was getting harder. Yet the challenges I face today as a the mother of a high schooler have somehow caught me completely off guard. 

Sometimes I miss those newborn sleepless nights, the toddler tantrums, and the nervous early school days. Sometimes I miss my little boy. Sometimes I want that finish line of childhood to stay in the distance just a little bit longer. 

My son is still a child but also an emerging adult

But, when this almost adult son of mine who towers over me, wraps me in his arms and tells me he loves me all while asking for $20 to go out with his friends, I’m reminded that balance still exists between the child and adult sides of him. 

Somehow, despite all the uncertainties and challenges that this stage of parenting brings, it also seems to be the best so far. There is space to just enjoy each other’s company and there is beauty in watching the rapid transformation that takes place in high school. 

Just as we did with every other stage of parenting, we will figure it out.

We will be ok, even when we cross that finish line.

You Might Also Want to Read:

To My Youngest as You Start High School: 9 Things I Want You to Know

About Jenni Brennan

Jenni Brennan is a psychotherapist, college professor, creator of Changing Perspectives, and co-host of The Changing Perspectives Podcast. Jenni is passionate about exploring the topics of parenting, relationships, grief, and mental health through her writing and podcast episodes. She lives with her husband, 2 teenage sons, 3 dogs, and 2 cats in Boston, Massachusetts. You can follow Jenni on Facebook at and on Instagram.

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