Resources

Surviving September: High School Edition

September brings a unique set of challenges for parents of high school-aged boys, too…but we’re here to tell you that success is closer than you think.

While the prep differs slightly from what we advise for college-bound students, the foundation for success is similar. Instead of focusing on weekly check-ins, we suggest hitting the organizational ground hard in the first four or so weeks of the school year.

It’s crucial for you to be “dialed in” during this time to help your son establish a routine that balances academics, extracurriculars, and personal responsibilities. However, we know this can be challenging, especially with boys who may resist structure and deadlines. Here are Causeway’s September Strategies to help you navigate this month effectively.


Understanding Your Son’s Underlying Emotions

mentor hugging young man on couch

As the school year ramps up, boys often resist schedules and deadlines, which can be a response to stress. This resistance can create a cycle where parental anxiety over upcoming tests and deadlines (and, let’s face it: grades) leads to increased teenage pressure…resulting in more resistance.

Instead of “force-feeding” dates and deadlines, our mentors use a more collaborative approach with our clients that works for parents, too:

Discuss the importance of deadlines with your son, and then ask for his input on managing his time. 

Example: If he’s overwhelmed by a football game, social outing, or general teenage life plans conflicting with study time, encourage him to brainstorm solutions for managing his schedule.

Encouraging Responsibility Through Natural Consequences

To manage resistance, allow natural consequences to take their course. If your son doesn’t prepare for a test or misses a deadline, use it as an opportunity for him to learn from his mistakes. Express your disappointment in his ability to manage his responsibilities, but avoid being overly controlling. Instead, take an authoritative approach—rooted in love and care—where you explain the importance of deadlines without being authoritarian. Remember, “boundaries are love” is an underlying approach to our Chief Clinical Officer’s purview on what helps family systems to work better.

Balancing Academics and Extracurriculars

Encourage your son to focus on his interests rather than what looks good on a college application. Pursuing his passions will make him more engaged and (hopefully) more willing to take responsibility for his commitments. As a parent, your role is to guide and support rather than dictate his choices.

Building Routines and Advocacy Skills

Help your son develop a routine that supports academic success. When we work with clients, we encourage them to use a calendar to track assignments and extracurriculars. (And if managing his schedule is just too challenging for him or for you, consider adding academic support services or tutoring for added structure and support.)

Fostering advocacy skills is also essential. Instead of solving problems for him, encourage your son to express his needs and think through solutions. If he’s struggling in a class or with a peer, ask how he plans to address the issue. This helps him develop problem-solving skills and become more self-reliant.


Remember: Navigating September requires patience, empathy, and collaboration. By engaging him in the process, allowing natural consequences, focusing on his interests, and fostering independence, you can help him develop the skills he needs to succeed academically and personally. This journey is a team effort, and with the right approach, it can be a positive experience for everyone under your roof. Click here to book an exploratory call to learn more about how our team can help you and yours.

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