Chicago-area parents share advice on sending kids off to high school

For most parents, the day they send their little one off to kindergarten for the first time is a major and memorable milestone. Moms and dads snap pictures of their precious 5-year-olds dressed in first day of school outfits to capture the big moment.

The Panel

Name: Cathy Brennan

Hometown: Chicago

Kids: Ferris, 19, Clare, 17, Jimmy, 14, and Aila, 7


Name: Amy Bizzarri

Hometown: Chicago

Kids: Daniel, 15, and Chiara, 6


Name: Brandie Langer

Hometown: Palatine

Kids: Abigail, 16, Emma, 13 and Carter, 10


Name: Kristine Prugh

Hometown: Chicago

Kids: Ronan, 14, Fiona, 12, Maisie, 8


Fast forward 10 (very quick) years and parents once again find themselves sending their (now not so little) child off for yet another big milestone: the first day of high school.

The first day of high school may look and feel different than the first day of kindergarten in many ways (and most high schoolers say no thank you to those first day of school pics), both firsts certainly stir up plenty of emotions!

We asked local moms who’ve sent kids off to kindergarten AND high school to reflect on the milestone days and share advice with parents facing these firsts this fall.

What you do remember most about sending your children off to their first day to kindergarten?

I won’t ever forget watching my son roll away on his bicycle, off to his freshman year of high school and my daughter smile and confidently wave goodbye as she entered her kindergarten classroom for the very first time—on the very same September day, this past fall. There is a 10 year gap between my two children; it seemed like just yesterday my son was the one going off to kindergarten and there he was, not only taller than me but on his way to high school. To say that the days are long but the years are short is the understatement of motherhood. Amy

I remember thinking how “grown up” they looked in their school uniforms and still how little they looked sitting at the tiny kindergarten-sized tables and chairs. It was a strange combination of big and little. Kristine

We only sent our youngest to kindergarten (the other two were homeschooled). We had planned to homeschool as well, but I was diagnosed with cancer over the summer and knew kindergarten would be the best thing for him. Because it was unplanned, I was really nervous about everything because we hadn’t prepared him for the transition. All of this was unfounded, of course. His teacher was amazing and not only did he do OK, he thrived in kindergarten! Brandie

How did YOU feel?

I felt happy for my kids, but the first day of school was always emotional for me. I remember crying in my car after dropping off. Not a sad cry, just a good old cry because they reached a new, exciting milestone in their lives. Cathy

I suggest having a plan for yourself after drop-off. Grab a coffee with another friend also dropping off at school for the first time. You will both enjoy it and it will solve the problem of “now what?” I often feel on the first day of school. Kristine

What you do remember most about sending your children off to their first day of high school?

I remember thinking “this is it.” I’ve raised them to be able to go off on their own and I have to trust that I have done a good job because I won’t be a part of their lives as much as I was in grade school. Cathy

It isn’t so much about dropping off as it is about them taking off. We didn’t drop our son off at school on the first day or any day of his freshman year. He simply got up, got ready and walked to the L. He “took off” ready for the adventure of high school. We were left behind vs. when we dropped off at kindergarten. Kristine

How did you prepare your child for the transition to high school?

We talked a lot about the fact that they would be given a lot of freedom and independence and they should not take it for granted. Cathy

When we sent my oldest to high school, I was worried about lots of things. Life is bigger and scarier in high school. I worried about bullying, sexting, drinking and drugs. We knew she was prepared academically, but I had forgotten the little things that can be worrisome: using a locker, changing for gym, who to sit with the first day of lunch. But I was also really proud of how mature and grown up she was. Brandie

Any general words of wisdom to share?

Don’t always assume the worst, and don’t assume that they are going to do the same things that you did when you were in high school. You have to let go a little and let them make mistakes. That is how they will learn and grow. Do trust in the fact that in the past 14 years, you have raised them and prepared them for this time in their lives. Plus, your kindergartner will hug and kiss you goodbye—that’s not always the case with high school students. Cathy

Be present. My greatest gift as a mother is to watch them spread their wings and head out into this big, wide, wonderful world. Inevitably, they will encounter roadblocks and bumps in the road, setbacks and stress, but also wonderful moments of smooth sailing and sunny skies. My job is to be present, love them and let them go. Amy

If the big day is bittersweet for you, honor both sides! You can acknowledge the sadness of it all and the amazingness of it all too. Brandie

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