Tips for High School Freshmen and Their Parents

A week from today, the youngest of our crew is heading to high school. I still can’t believe it! But Jimmy is so ready. He would have gone to high school two years ago if St. Mary’s would have graduated him a little early. A lot of this readiness comes from being the youngest of five. Jimmy has seen a lot!

But it’s also so much easier getting Jimmy ready to start high school because of the older kids. It wasn’t this way at all when I sent our first child Grace. The whole idea of a public high school was new and kind of scary to me. All of my education, from kindergarten to graduate school, had been in Catholic schools so a big high school was whole new world. I remember when we got to book pickup, I hadn’t checked the right box so we had to go back the next day to get the them. This wouldn’t have been so bad if I hadn’t also not submitted her physical form before her first day of cross country tryouts and the coaches mader her sit that day out. Ugh! Needless to say, there have been a few lessons learned.

Someone told me before Grace started high school that 98% of kids find their way once they get there. The other 2% need a little extra support and may find themselves somewhere else. That has been so true for us. No two of our kids have followed the same path. Grace did cross country and yearbook, Eddie did football and student government, Leo was sports and more sports, and Annie has played tennis and volunteered with any program where little kids are involved. It’s going to be so much fun to see how things unfold with Jimmy.

Tips for Parents

I’ve been thinking a lot about what I wish I knew about being a high school when Grace was starting. Here are a few things:

  1. Let the kids advocate for themselves. Our local high school is a huge supporter of this. And it’s so great to be able to watch your kids take these steps towards adulthood while you’re still close enough by to catch them if you need to.

  2. Trust your kids until they give you reason not to. We were so strict with our oldest son who was always looking for the fun. I was terrified that he was going to get into trouble, so we kept him on a very short leash. This totally backfired and forced him to sneak around us in order to have a normal high school life. So again, trust your kids until they give you reason not to. This is a much better plan. (Thankfully our sweet boy turned out great in spite of me being so tough!)

  3. Volunteer where your kids are. What brings them joy will likely bring you joy, too.

  4. Go to as much of the high school fun as you can. It all goes so fast. When everything was shut down during Covid, I realized quickly how much I missed being part of everything. So as soon as the world opened up, I went to everything I could and have been so grateful for that.

  5. Give yourself grace. You’re going to make mistakes. But as long as your heart is in the right place and the best interest of your child is your guide, don’t beat yourself up when things don’t go perfectly.

Our full crew of graduates from the School of St. Mary

Tips for Your Freshman

When we were on vacation last week, I asked each of the kids to give Jimmy some advice to start his high school career on the right foot:

  1. Start strong. Get good grades from the beginning because freshmen year is a lot of review so it’s easier to do this. These good grades come in handy when the harder classes come along and you need a little padding in your GPA.

  2. You need just one good friend. You don’t need a whole group. One solid good friend is all you need in your corner.

  3. Play a sport. (Not hard to figure out who said this!) But coming from a small school, joining a fall sport or club was so good for my kids. Their worlds immediately got bigger!

  4. Invest yourself in something. Lean into your schoolwork, a sport, or an outside activity you care about.

I thought these were really good and balanced out the “don’t let mom talk you into clear braces,” “don’t spike your hair,” and “know where the clean bathrooms are.”

Additionally, my daughter Annie has nailed the school supply shopping list. I let her take Jimmy to get what he needed and everything they bought fit into one bag from Target. Here’s a photo of what they bought.

Here are Annie’s top picks:

A five subject notebook and big binder with a divider for each of your classes: This is genius! By carrying just these two pieces, they have everything you need for all of your classes (especially since freshmen lockers tend to be too far away to be useful).

A planner (not shown here): Annie maps out her all of her classwork every week. I know this is unusual for most high schoolers, especially boys, but she is rarely stressed and always seems to have time for her friends and babysitting jobs because of this. I ordered this one for Jimmy and am hoping he will use it.

Gum and deodorant: These were my favorite! Annie assured me that all freshmen boys absolutely need these in their backpacks for after their gym classes. (And she recommends that girls pack all the girl supplies they might need, plus a little perfume roller for after gym. I think she had gym first or second period when she was a freshman…she knows what she’s talking about.)

I hope this is helpful in these last few days leading up to high school. It’s going to be great!


My name is Ann Marie Scheidler and I'm thrilled you've decided to check out my blog. I'm a pearl-loving yogi with a thing for travel, a weakness for beautiful bags, and a passion for storytelling. In this space, I'll be sharing stories about my family, go-to recipes, my wellness journey, fashion and beauty favorites, and my love for Chicago’s North Shore. I find new inspiration wherever I go. Thanks so much for coming along for the ride!


Find out all that’s new on the blog right from your inbox! Sign up for the newsletter today!

Leave a Comment


  1. Meghan wrote:

    This is terrific! Our 5th (and 3rd boy) is also starting high school. This spoke to me on many levels – and some great new tips.Love it.

    Posted 8.10.22 Reply
    • Ann Marie Scheidler wrote:

      Another mom of 5! I love it! I am sure you could add many tips to this list! xo

      Posted 8.10.22 Reply
  2. Mary Stevens wrote:

    I think this is my favorite dress ever!

    Posted 8.10.22 Reply
    • Ann Marie Scheidler wrote:

      Really? I think mine, too! xoxo

      Posted 8.10.22 Reply
  3. […] Back-to-School Shopping: In case you missed it, my daughter Annie has perfected the back-to-school shopping list for high schoolers. She took my son Jimmy and got everything he needs for his freshmen year, including a couple of things I never would have thought of. I recapped it all in this post earlier this week. […]

    Posted 8.16.22 Reply