How to Help Your Child Navigate the Awkwardness of Middle School

Is there any time in a tween's life more awkward than middle school? Here are seven essential ways to help your child rise to the challenges.

Cheryl Butler
9-minute read
Episode #552

Most kids are thrilled to move on up from their elementary days to the seemingly more mature world of middle school. But once they find themselves in that strange new environment, they soon realize middle school is one of the most daunting transition periods of their lives. Along with new academic demands, and the awkwardness of having to navigate a whole new social landscape, they face surging hormones and emotional challenges

Turns out, the new normal is not so normal at all.

These seven tools can help you and your child navigate the tricky middle school years positively. It's possible to enjoy this time instead of dreading it! We'll talk about how you can:

  1. Set clear expectations for studies and free time
  2. Encourage feelings
  3. Make room for digital downtime
  4. Nix the negative
  5. Teach your tween to self-advocate
  6. Stay connected, and
  7. Cultivate a can-do attitude

Parenting middle schoolers is just plain hard

Each stage of parenting presents its challenges, but the middle school years can be especially tough. Researchers at Arizona State University surveyed mothers and discovered that, on average, moms of kids age 12-14 were a lot less satisfied as parents than the moms of infants, preschoolers, elementary-aged kids, and high schoolers. 

Whether they like it or not, your tween still needs boundaries and lots of guidance.

As a mom currently raising her eighth middle schooler, this data isn't a revelation—I can totally relate! Tweens are ready to exert more independence. They crave more opportunities where they don’t need as much parental supervision. That's a normal part of development. But, whether they like it or not, your tween still needs boundaries and lots of guidance.

So, let's look at how you can help keep your middle schooler on a happier track.

1. Set clear expectations for studies and free time

Once your tween gets a taste of middle school independence, she might feel unstoppable. Or she could feel the opposite—completely overwhelmed. Parental handholding may be a thing of the past with your middle schooler, but it’s still important to set clear guidelines on important areas like homework, chores and responsibilities, downtime with friends, and basic household rules.

I equate this to my full-time job as a development assistant. My boss doesn't feel the need to hover and micromanage my weekly schedule, but he does have expectations for my job performance. We schedule regular blocks of time to update one another with my progress, address concerns, and exchange ideas.

Set aside one-on-one time to have a conversation with your child about the exciting opportunities that lie ahead, and be specific about what your expectations are. Here are a few questions to talk through with your tween.

  • What’s the plan for homework each night? Ask her where she's most comfortable studying. Be realistic about how much time should be set aside, especially if your child is involved with school sports or an extracurricular activity. In other words, don’t wing it. Sure, there will be nights when a schedule doesn’t go according to plan, but if you and your child have a consistent study routine in place, you’ll eliminate the unnecessary stress of scrambling to keep up the grades.
  • What are your tween's responsibilities? As your kids grow, it’s important to revisit their responsibilities. These might be things like managing regular chores, meeting curfews, respecting screen time allowances, and taking care of their bedroom. Tweens may not need as much supervision, but they aren’t mind readers. They both need and deserve to know what your new expectations might be. Have a chat to make sure you're both on the same page.
  • What are your expectations for hanging out with friends during the school week? Are you comfortable with your child hanging out at a buddy’s house where there's no supervision? Be clear and consistent when communicating about this subject so your child will learn to respect and follow these guidelines.
  • What does your tween need from you? Ask her where she might need help. Does she need gentle nudges about homework and completing school projects on time, or would she prefer to take charge of her schedule? Get in the habit of asking how you can help, even if it means simply listening to her vent when she needs to get something off her chest.

RELATED: 4 Reasons Communication is Crucial in Parenting

2. Encourage the sharing of feelings

Some kids are much better at expressing their emotions than others. Two of my eight kids can easily relay why they’re having a great day or what’s got them troubled, but several of them would rather clean all of our bathrooms than have to open up about what’s on their mind.

Middle schoolers seem to have more difficulty sharing their feelings because they haven’t learned to manage them yet. They often place blame for their feelings on an outside source and lack the proper coping skills to deal with them. It's no wonder they're often labeled as moody!

Have conversations about feelings with your tween regularly.

In my interview with Mallika Chopra, author of Just Feel: How to Be Stronger, Happier, Healthier, and More, she stressed the importance of helping kids understand that their feelings are potent and affect both their mood and choices. Her book provides mindful exercises that show kids how to identify their feelings, express them, and make good choices.

Have conversations about feelings with your tween regularly. Ask him to tell you about times when he felt certain emotions like excitement, anger, or relief.

Label feelings as you observe them. When you notice your child struggling with pre-algebra, you can comment “It seems like you're frustrated with math. I don't blame you! You’re working extra hard to understand the concepts, and I admire you for sticking with it.”

Labeling feelings not only helps kids learn about verbalizing their emotions, but it helps to normalize the range of feelings we all experience every day. Remind him that mom and dad feel frustrated sometimes, too.

Teach that emotions change constantly, and the way they feel in the moment isn’t permanent. You can respect your child’s feelings in the present while also reminding them that it’s not forever.

3. Make room for digital downtime

Today, our kids have full agendas and are seldom turned off from the outside world. Their ability to stay connected to social media and dozens of other cyber platforms via smartphones and electronic devices leaves hardly a moment for them to be alone with their own thoughts.

Making room for digital downtime can offer great value to harried middle schoolers.

Encourage short sessions of quiet time without smartphones or devices. Making room for digital downtime can offer great value to kids of all ages, but it's especially important for harried middle schoolers.

The benefits of taking a break from the onslaught of digital distractions include finding respite from social and school demands, emotional renewal, a chance to connect with their creative selves, improved concentration, and an overall feeling of peace and calm. When one of my tweens seems headed for a meltdown, I immediately suggest they turn off their electronics and tune in to themselves.

4. Nix the negative

I’m a Pollyanna by nature, but as the busy mom of eight kids—all close in age—my even-keeled nature has been tested more times than I can remember. If there’s one thing I continually try to improve upon as a parent it’s my ability to stay positive towards my family.

Human beings crave acceptance and acknowledgment. This craving is no different for kids.

By nature, human beings crave acceptance and acknowledgment. This craving is no different for kids. When we tend to focus on all that a child does wrong, we draw attention to what's not working instead of the things that are great.

Instead of saying "You're so moody all the time!" say "I love how you always wake up with a smile!" Look for things to reward instead of focusing on things to criticize. Shifting the focus to what's positive rather than what's negative can boost your middle schooler’s self-esteem a mile high!

Pro Tip: It's important to connect with other parents who are experiencing the middle school years, but be careful to keep intimate, personal details out of the conversation when you vent. Stick to general topics ("It sure can be frustrating when our kids are in a mood!") rather than specific ones ("I hate when my son starts stomping around, slamming doors, and having a full-on temper tantrum!") Never throw your child under the bus, no matter how frustrated you are, or you risk very private things being broadcast publicly.

5. Teach your tween to self-advocate

Every child has different needs, and you will not always be there to intervene when she needs help. Middle school is a time when academics become more challenging. Middle schoolers are expected to manage multiple classes and navigate the hallways with all of their materials.

My daughter, who's graduating from college this year, had a significant speech delay when she was a young child. Because of that, she has had to work twice as hard as her peers to complete her school assignments. 

Not only is self-advocating a wonderful skill to acquire in middle school, it’s a valuable tool for life!

Once she was in middle school, one of her biggest obstacles was processing some of the oral instructions her teachers gave. If they were speaking too fast, she had great difficulty comprehending what was being taught. Many times, she had to stop the teacher and ask him to repeat what he'd just said.

At first, her peers made fun of her. But because we roleplayed at home about how to appropriately ask for help, she became very confident in her ability to get clarification on anything she didn't understand, even in front of a class full of other kids. By the time she reached high school, kids loved being in classes with her because she was one of the few students brave enough to raise the questions others were thinking but didn't have the courage to ask.

Not only is self-advocating a wonderful skill to acquire in middle school, it’s a valuable tool for life!

6. Stay connected

Tweens like to be self-sufficient and want us to believe they have everything under control—but that doesn’t mean we parents shouldn't keep the lines of communication open and flowing.

When you ask your tween questions, make them open-ended so your child has to give more than a yes or no answer. For instance, instead of asking your child whether they had a good day in their current events class, ask what story in this week’s newspaper the found most interesting. 

Texting is also a great way to stay connected throughout the day. If your teen has a big game after school, send a quick message: “I hope you and the team have a great game today. I'm excited to hear all about it tonight.”

Pro Tip: I started a communication tool I refer to as “Love Mom” journals for each of my kids when they started middle school. Each of my older children has a notebook they keep in their bedrooms. This is a safe place for them to mention anything that might be on their minds. They have expressed simple things such as wanting an upgrade on their phone because they dropped it and cracked the screen (ugh!) to something more personal such as being embarrassed that they have body odor. We go back and forth exchanging quick comments in the book, and it truly only takes a few minutes each week.

7. Cultivate a can-do attitude

As a parent, it’s never easy to hear your child express negative thoughts or to see her wallow in self-pity and feel down in the dumps when things aren’t going well in her world. Unfortunately, it’s natural for people to dwell more on negative thoughts than on positive ones, and this can be even more true for tweens.

As parents, there’s plenty we can do to help our children develop a more can-do attitude about themselves and their world. For starters, taking the time to let them know that feeling sad and down is normal can make a huge difference.

However, I want to note it’s extremely important for parents to pay attention to their teen's mood and make sure that there are no signs of serious depression beyond moodiness. It's important to understand the difference between the two

RELATED: 11 Little-Known Signs of Depression

  • Teach your child to use positive affirmations. When she’s preparing for a difficult science test, encourage her to say “I know I can do this” instead of “I stink at science.”
  • Set goals. Goal setting is a great tool to measure positive wins. If we write our desires and aspirations down on paper or keep a digital copy on our computer, we take responsibility for trying to achieve them rather than just daydreaming about them. Just as important as writing down the goal is listing ideas and actions for making it happen. Goals create a sense of purpose and growth.
  • Develop skills and passions. If your child is passionate about an activity like drawing, dancing, or hiking, tune in to these strengths and help him develop and grow these skills so he can feel successful as he’s learning.
  • Model a positive attitude. One of the best ways to help your child take a more positive approach to life is by setting an example. Being a negative Nellie and putting yourself down in front of your kids (“I hate how I cook mashed potatoes. Will I ever get a simple meal right?”) is a total downer. Instead, stay positive. (“My potatoes were on the lumpy side, but the stuffed chicken breast and chocolate cake were delicious!”) Positivity is contagious!

One thing that continually blows my mind is how fast my kids have grown up. When I had eight kids ages 12 and under, I wasn’t sure I’d ever visit the bathroom alone again, never mind coming close to having an empty nest! Now, my oldest daughter is married and a new mom herself, and several of my kids are in college or already graduated.

Middle school is a time to embrace. Kids this age are old enough to enjoy more independence, develop their unique interests, and work on the traits that will lay the foundation for adulthood. And yet, they’re still young enough to be playful and to need you. It’s a special time, and believe me, it goes by fast. Relax and enjoy the ride!


Cheryl L. Butler is the mother of eight children. Her experiences with infertility, adoption, seven pregnancies, and raising children with developmental delays have helped her become a resource on the joys and challenges of parenting. Call the Mighty Mommy listener line to leave your question at 401-284-7575. Your question could be featured on the show. Stay in the parenting loop! Listen and subscribe to the Mighty Mommy show on AppleSpotify, or wherever you get your podcasts.

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All content here is for informational purposes only. This content does not replace the professional judgment of your own mental health provider. Please consult a licensed mental health professional for all individual questions and issues.

About the Author

Cheryl Butler Project Parenthood

Cheryl L. Butler was the host of the Mighty Mommy podcast for nine years from 2012 to 2021. She is the mother of eight children. Her experiences with infertility, adoption, seven pregnancies, and raising children with developmental delays have helped her become a resource on the joys and challenges of parenting. You can reach her by email.