Repeat or stay the course?

That is the high school question. 


Your son or daughter repeating a year in high school is NOT defeat, 
but an opportunity and could be the key to your child’s success 


(Download article here.)


When parents consider having their child repeat a year in high school, they oftentimes think that their current school system has failed them, or that their child is not a good student. 


But most times, it’s quite the opposite. For students in high school, repeating a year offers innumerable positives and allows them to recover a “lost year” and get back on track to success. It’s a chance to build upon existing skills and talents, a time to expand and try new things, and improve their academic profile, well prepared for the college process and experience.


Students often enroll in an independent school to repeat a year because their public schools did not meet their expectations. Deciding if and when your child should repeat a year can be a daunting task and an emotional commitment.


How do you decide? 

And what factors should matter most? 


The benefits and values of this decision listed below should help make the process easier for you.




Academic Strength: Expanding one’s knowledge 


Oftentimes, high school students and their families consider repeating a year for academic reasons, because something they needed was missing in their current environment. That could be:

  • a lack of support and trust, resulting in poor grades or performance  
  • too few academic challenges and course options, leading to disinterest, boredom, and coasting through these critical academic years, or even simply 
  • running out of advanced options having maxed out the curriculum, leaving you frustrated and unfulfilled 


Students repeating a year quickly discover what was missing can indeed be found at an independent school. Smaller class sizes, stronger relationships with teachers, coaches, and staff, personalized attention from attentive and caring adults, engaged and motivated peers, and a wide breadth of course offerings are just the tip of the iceberg when it comes to new experiences and greater benefits. Independent schools offer a student-centered approach to teaching and assessment, affording multiple opportunities for students to demonstrate what they know and how they have improved at a time when they are ready to show it.  


Athletic Prowess: Practice, practice, practice 


Professional and student-athletes alike continuously find ways to get the upper hand on their competition. Repeating a year (also known as “reclassifying”) is another way to help a young adult grow taller, faster, stronger, and more mature both on and off the field.


Many times, student-athletes will repeat a year to secure additional playing time, learn from new and experienced coaches, hone their athletic skills, garner more attention from recruiters, and expand their “film time” portfolio and applicant profile. At an independent school, athletes can compete in different leagues at higher levels with a diverse and complete roster of talented players. 


“I always like seeing kids that repeat a year because they are betting on themselves,” one Ivy League coach said.


“They have an opportunity to get bigger, faster, stronger, more mature, and continue to grow and develop as a football player…while also improving and growing academically which will help them prepare for the rigor of an Ivy League education.”  


Individual Path to College: Standing out among peers 


Picture this: Your child is completing his or her sophomore year in high school. With little direction, they are uncertain about what colleges to consider, which universities are what they appear to be, what career paths they should explore, and how they should go about managing this complex and confusing process.


Who is there to help them—and you—navigate such harrowing territory?

Who knows your child well enough to provide personal advice, appropriate direction, and professional guidance? 


Independent high schools offer unparalleled and powerful partnerships between college counseling staff, students, and parents. Dedicated, full-time professional college counselors bring expertise and have access to myriad resources. They specialize in the field and focus on the unique needs and potential of each student whom they advise. Their backgrounds, experience, and insights, along with their close relationships with college admission officers, go beyond the average high school guidance counselor.


“When a student leaves what is comfortable and commits to a new academic, social, athletic, or extracurricular life, it sends a powerful message to college admission officers that the student cares deeply about their education,” said Madeleine Bergstrom, director of College Counseling at Cheshire Academy.


“Students who choose to repeat find that extra year to be an incredible opportunity to grow personally and academically. At independent schools, you have a dedicated professional college counseling staff in place to support a student every step of the way and a community rallying around the student’s success. Our network is broad, and we take the time to get to know our college representatives, building strong relationships with schools across the world.”  


Most important, students who repeat a year will not feel lost in the shuffle as they (and you) will experience a very individualized and thoughtful college research and application process. 


Ready for More: New challenges and unique opportunities 


On most college applications, repeating a year of high school will stand out. Is that a “red flag” or a distinct advantage? In many cases, students at independent schools have a chance to highlight and write about their desire for academic challenge, a new start, greater opportunities, or growing up as reasons that prompted their decision to repeat a grade. It is viewed as a wise choice, a commitment to doing more or doing better, and shows self-awareness and confidence—qualities that are real strengths in young people.


By repeating a year at an independent school, students demonstrate that they are not satisfied with the status quo. They want to open doors to new experiences and opportunities. A rigorous academic course load, club, special interest, or new talent may spark another passion for a student-athlete. The artist, musician, and budding scientist will find venues and opportunities to showcase their talents. The breadth and depth of the independent school experience will only increase their chances and competitiveness as they strive to get accepted to colleges and universities of their choice.  


Gradual Independence: Growing up before moving on 



For most students enrolled in a public or parochial school, heading off to college will be the first time they will truly be on their own. As such, they will need to have the executive function and life skills necessary to flourish in a completely new environment without the support and assistance of others. 


Is your child ready to manage on his or her own? Are you nervous about the challenges and obstacles they will face? 


Maybe your student is not socially or emotionally mature to a level you believe is right for college. They may have even started school at an age younger than their peers. Repeating a year will provide them additional time to “catch up” in that regard, and grow as an individual ready to take on greater challenges.  


At an independent school, students also have the chance to learn life and leadership skills, such as work ethic, being a contributing member of a community, and time management. . It’s the perfect transition from home toward independence, surrounded by likeminded classmates, peers, mentors, and friends who have the desire to learn, participate, and achieve, while being exposed to different cultures, backgrounds, and even languages they might never experience otherwise. 


Independent schools offer the best of both worlds: gradual independence while being surrounded by attentive, trusted, and supportive adults who know and care about their students. And they create the college-like experience without the isolation, the sink-or-swim atmosphere, or the completely unguarded borderless, environment parents often worry about and fear. 


“Our son deciding to repeat junior year was one of the best decisions we’ve ever made. Any concerns we had regarding how a repeat year would be perceived were immediately forgotten and the transition was seamless. From making sure he was comfortable in the dorms and challenged in his classes to ensuring that his college applications accurately reflected his academic journey—we cannot imagine a better school or a better outcome.”

25% of our newly enrolled students are repeating a year


Having now reviewed the benefits of a repeat year, take the next step and speak with someone about how to move forward.


At Cheshire Academy, our Admission team is ready to talk with you about your child’s stage in school and answer any questions you have. Reach out by calling 203-439-7250, send an email to admission@cheshireacademy.org or to be notified about our upcoming online events, please fill out the form below.