October is a subtle shift from September’s back-to-school frenzy to a more reflective rhythm. With changing leaves and cooling temps (and even the seasonal invasion of pumpkin spice every.single.thing), this gentle transition makes October perfect for checking in on your son and evaluating his first month of school. 

(If he’s thriving, great. If not, it’s the perfect time to tweak his support systems so that he does). 

Vince Benevento, founder and CEO of Causeway Collaborative, has seen this season before. “This is the juncture where families start to get real insight into how their sons are performing,” Benevento says. “Academically, socially, and mentally—parents now have enough information to see whether things are going smoothly or if intervention is needed.”

But you and Vince know that school success is about more than grades. It’s about how our sons show up in the world—how they’re managing stress, balancing responsibilities, and connecting with those around them.

With more than 10 years helming Causeway Collaborative, Vince’s insights and tactical tips are here to help you and your high school and college-age sons keep taking the right steps in the right direction.

The First Check-In: Is Your Son Thriving?

Whether he’s a high school freshman adjusting to new classes or a college sophomore tackling independence, patterns emerge as the chaos of the school year’s “firsts” subsides. 

“Parents are now able to pick up their heads and are beginning to see grades in different classes,” says Benevento, adding that they may now be seeing their son’s habits more clearly. That makes October the month when you might notice if your son is struggling to manage his responsibilities.

Ask yourself: Are you aware that his grades have slipped? Is he glued to his gaming console the second he gets home? While video games aren’t the enemy, if they’re replacing meaningful activities or social interactions, it might be time for a gentle course correction. At Causeway, that means it might be time for mentorship.

Mentorship + Structure = A Lifeline for Boys

Benevento suggests considering mentorship. “Mentorship can be a powerful way to introduce structure where it might be lacking,” he says.

“Mentorship presents as a wonderful option for parents who see that their son isn’t really engaging effectively after school,” says Benevento. If you see your sons are disengaging after school—whether through excessive tech use, withdrawal from social circles, or a lack of interest in anything beyond the classroom—mentorship offers your son a guide—someone outside of the family dynamic who can provide support, accountability, and encouragement. Maybe your son isn’t quite ready to talk about what’s bothering him, but a mentor could be the person who gently helps him open up.

Navigating Holiday Stressors

October doesn’t just mark the settling of the school year. As we move toward Thanksgiving, Jewish holidays, and other seasonal celebrations, it’s worth remembering that your son might be feeling the weight of unspoken holiday stress (both his and yours). 

“Students, young people, and young men, are picking up on those factors. So we may see guys who are stressed about the holidays, but they don’t have the language to articulate those concerns or to share their thoughts and feelings.”

Vince suggests encouraging open, non-judgmental conversations during this time to help alleviate some of the pressure he’s feeling…even if those talks are short and sweet.

Exploring Outlets For Stress That ‘Pay’ Off 

For older high school students, October can also be the perfect time to explore part-time work opportunities. With college students returning to school, seasonal jobs often become available, giving your son a chance to engage in something beyond the classroom or his bedroom. 

Vince suggests that a part-time job can complement your son’s school day. It’s not just about keeping him busy. and maybe also helps unearth his personal interests. 

It’s about giving him a sense of responsibility and accomplishment—something that helps build confidence and independence and might even help him unearth some of his personal interests.

Plus, extra spending money never hurts, right?

VINCE’S TIPS

Need to “unstick” your stuck son? These tools will help move him through life if it trips him up.

Identify His Thing

“I’ve long said that every kid has a ‘thing’ that will unlock his potential, and your job as a parent is to help him match his thing to an activity of interest for him. Whether it’s music, sports, friendships, or even a video game club, connecting to his ‘thing’ can unlock his potential and foster meaningful relationships.”

Develop a Routine  

“Whether it’s fitness, wellness activities, or chores around the house, daily structure and a clear routine can boost his efficiency and help him accomplish more tasks each day. (And if executive functioning is an issue, give him some help with sequencing in terms of what to do first, second, third, or fourth each day). Tying actions he does every day to the thing that makes him happy can later be tied to helping him identify possible careers or areas of life interest.”

Seek Mentorship  

“If you’re struggling with helping your son to identify their ‘thing’ or to create a routine, our mentors can serve as a valuable support system to facilitate your son’s growth.”

Do you have a question or concern you’d like us to address in a future issue of Causeway Connection? Email us at hello@causewaycollaborative.com and we’ll prioritize getting you the answers you and your family need to not just survive but thrive in navigating your son’s adolescence and young adulthood.