More Than A Fresh Start

The start of a new school year brings fresh haircuts, new shoes, and that classic blend of excitement and nervousness. Our boys hear a consistent hum, “try something new”, “make new friends”, and “do your best”. All of these are great messages, but can we match those messages with further support? With the summer behind us, there is an opportunity for all of us to try to strengthen our connections and grow alongside the boys in our lives.

Boys of today are navigating adolescence in a remarkable and often contradictory world. We have the convenience of cutting-edge technology at our fingertips and seemingly endless ways to connect, yet meaningful connection seems to be more difficult than ever to foster. Our boys can enter a streaming community with people around the world in an instant, while struggling to feel known by the people and communities who surround them. The unfortunate truth is, our boys are growing up in a time when trust is lower, social circles are smaller, and genuine relationships across generations can be harder to find. A fresh start should certainly be about new experiences, but it should also be about strengthening the relationships that give boys the support to embrace those experiences. 

We can achieve this by giving boys the space to struggle and fail, while showing them what it looks like to navigate those moments ourselves. We can also look beyond our own sons and recognize the opportunities we have to show up and build a steady presence for the different boys who find their way into our lives.

 

Failure and Connection

Trying something new always comes with the possibility of failure. It might be taking a challenging class or trying out for the musical. If these new experiences go awry, many of us are quick to step in and try to fix the situation. We must fight those natural tendencies to make the path in front of our sons easier. We want to protect boys from disappointment and discouragement because we care deeply about them, but that ends up doing more harm than good.

In Raising Mentally Strong Kids, Dr. Daniel Amen and Dr. Charles Fay emphasize the importance of helping children develop the capacity to navigate challenges themselves. As they write, “Building something strong takes a lot more work and sacrifice than building something weak. To raise strong kids, capable kids, we have to put aside our desire to always make our kids happy and comfortable.” That means resisting the instinct to remove the obstacles in a boy’s path. Instead, our role is to stand beside him through the hurdles he faces, offering support while giving him the space to struggle and become increasingly capable of handling what comes his way.

Allowing boys to face challenges does not mean we have to watch from the sidelines. Boys should not be alone in these experiences with failure. They need to see us fail, too. We ask our sons to take risks, admit mistakes, persevere, and try again. They should see the adults around them do the same. That means stepping out of your comfort zone in full view of your boys. Try to learn that instrument you’ve been saying you’d take up for years. Get out on the dance floor.
Take the microphone during karaoke. Attempt that new language. Pull out that old skateboard…and your helmet. Whatever it may be, let them see you out of your comfort zone.

Show them how to navigate the feelings of anxiety and potential embarrassment when things don’t go right. Model having the courage to give it another shot even though you came up short. This may be one of the most authentic ways we teach them to access perseverance and grit. Although you may have to deal with the secondhand embarrassment “cringe” comments that come from your teenager, deep down it will build his resilient spirit, and yours.

 

Showing Up for Boys

These opportunities are not limited to our own sons. The way we show up and respond matters to the other boys who find their way into our lives as well. Dr. Brooklyn Raney’s book, One Trusted Adult, reminds us that we do not need to be every boy’s “person." As adults, we can only go 50% of the way in building a relationship. The other half belongs to the boy, and sometimes he may not be ready or willing to meet us there, and that’s ok. Think about the boys who come through your front door, sit around your kitchen table, ride in your car, or spend time with your family. How are you showing up for them? We can make ourselves available without forcing connection. We can take an interest, ask questions, listen, and maintain boundaries while leaving the door open for a connection to develop.

These relationships are often built through consistency rather than a single meaningful conversation. Boys need to know that our interest in them is genuine and does not disappear when they are quiet or uninterested in us. Sometimes showing up means asking the question and accepting the one-word answer. It means simply being present enough that a boy knows where to turn when he is ready. Trust takes time, and we may never clearly know which seemingly small interaction helped a boy recognize that another adult was in his corner.

What is clear though is the research behind Dr. Raney’s work and just how much these connections matter. When a boy can identify at least one trusted adult, the likelihood of a number of harmful outcomes, such as substance use and suicidal ideation, decreases. Ideally, as Dr. Raney describes it, when young people develop an entire “bench” of trusted adults they can turn to, the numbers become even more positive. The more trusted adults in a boy’s corner, the better, and we can all be one adult who is available to the boys in our lives.

 

A Fresh Start for All of Us

A new school year is a fresh start for our boys, but maybe it should be one for us as well. This school year, encourage a boy to take a chance. Give him room to fail, and let him see you fail, too. Show up for your son and look for opportunities to be there for the other boys who find their way into your life. We cannot reverse every trend around trust and disconnection, but we can positively influence what is directly in front of us. We can build homes, schools, and communities where boys know adults are standing right there beside them, even when things do not go as planned. That seems like a pretty good place for all of us to start.

 

The conversation continues on the Boys Education Series podcast! Listen on Apple Podcasts and Spotify.  Subscribe on your favorite streaming platform.

Matt McCarter, Director of The Center for the Education of Boys

Matt McCarter serves as Director of the Center for the Education of Boys at University School, where he also teaches Global Dynamics and serves as an assistant varsity wrestling coach. With nearly two decades in education, he has worked in public, independent, and international schools, including serving as President of the Chengdu International Schools Association in Chengdu, China. At University School, he founded the eighth-grade Capstone Project, a year-long, student-driven exploration of food insecurity in Northeast Ohio. In 2025, he was awarded the W. Hayden Thompson ’45 Chair for Exceptional Faculty Leadership.