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A User's Guide to Surviving Boarding School

Words of wisdom from a rising sophomore

Several years ago, I contributed to a book titled Where Should I Sit at Lunch? The Ultimate 24/7 Guide for Surviving the High School Years (McGraw-Hill, 2006) by Harriet S. Mosatche and Karen Unger. Covering more than the classic cafeteria dilemma, the real-life stories of teen collaborators offer guidance on a host of other issues, such as peer groups, homework, part-time jobs and colleges.

As difficult as the transition to high school might be, it may be amplified for young people leaving home for boarding – or independent – school. And, while I serve a number of national organizations as a “parenting expert,” I never attended school away from home. Thus, I turned to a real expert, John Calicchio.

John is a 15-year-old rising sophomore at Kent School in Connecticut. He serves as Class Representative, an elected position, plays varsity lacrosse and was the 2014 recipient of the Mount Algo Award for excellence in writing. He offers his advice for parents and teens embarking on the boarding school experience.

When I was applying to high schools, I was looking for a school that offered an exceptional education, great athletics, opportunities to open doors for me later in life and a community of people who shared the interest of excelling. Boarding school was the perfect fit.

Preparatory school obviously gets you prepared for what colleges are going to expect from you, but they do this in a manner that is relatively difficult at first. That is why I am here to give you my Top Ten Tips for Making the Transition to Boarding School Easier.

During my first day or two at school, I was very anxious about meeting new friends. I shouldn’t have been nervous, because everyone was so friendly and welcoming. I made so many friends in the first week and I think this is because I came in as a freshman and all of the other freshmen were in the same boat. Nobody really knew one another, so we were all trying to make friends.

Tip #10: My biggest tip to all new students is be outgoing during the first week. Go to all of the activities the school has to offer and make friends. I believe having strong relationships is extremely important.

With that being said, it is also very easy to get distracted from your school work in order to socialize. If you are in your dorm room doing homework, it’s tempting to go to another dorm room and chat with a friend. This isn’t a huge problem, but normally a quick chat ends up being a long conversation having nothing to do with homework. This a serious problem. Tip #9: I highly recommend going to the library. It’s a quiet place where you cannot socialize and get distracted.

Tip #8: Another great tip is to use your resources! For me, going to the writing lab was the greatest thing I have done to improve my writing. Whenever I had an essay or a research paper, I would always go straight to writing lab for help. Tip #7: Also, if you are ever having trouble understanding something in a class, email or talk to your teacher right away. Don’t go to a third party, because the teacher knows the material best. This also goes for athletics. If you ever want to improve your footwork or get a workout plan, talk to your coach of any sport and he or she will lead you in the right direction.

My grandfather once told me, “Prioritize your life and aim above your goals.” This was great advice and extremely useful. Tip #6: Right when you get to boarding school, set your goals and your priorities. In my opinion, grades always come first. Personally, I want to continue my love for the game of lacrosse and play in college. I know I won’t achieve these goals unless I have the skills but, more important, the grades. I also recommend you set your goals high.

Time management is vital at boarding school because you don’t have a lot of free time with school, activities and homework. So in your free time, it’s easy to do things that are not related to school, which is OK to a certain extent. Tip #5: I recommend being productive with school work when you have free time, but it’s also important that you socialize.

Organization is crucial in boarding school. You normally get a lot of papers and it is not easy to stay organized. Tip #4: I recommend getting three-ring binders for every class and for every semester. This might seem unnecessary, but it’s worth it. You can reuse each binder every year. Also, keep your room clean and neat. It is good to live in an organized environment!

Finally, there are a few things I recommend you bring with you to prep school.

Tip #3: Mattress pad – It is very important to get a good night’s sleep, and most of the time the beds at schools aren’t very comfortable.

Tip #2: Reminders of home – Bring with you to school anything that reminds you of home. It’s always nice to have something that reminds you of your family.

Tip #1: A calendar – Having a calendar is a must for me. It’s good to have little reminders to help you with time management.

John also weighs in on how to steer clear of trouble. He says, “Staying out of trouble is easy. I recommend hanging out with those who appear to others to be ‘good kids.’ If you’re running with the wrong crowd, you might not only get into trouble but also earn a reputation of being mischievous. If you are ever in a situation where you don’t know what’s right and what’s wrong, ask yourself, ‘Would my mother approve?’ After all, if it doesn’t help you to achieve your goals, it’s probably best to say no.”

Good advice from a great kid! Pass it on.

Stephen Gray Wallace, director of the Center for Adolescent Research and Education (CARE), has broad experience as a school psychologist and adolescent/family counselor. He is also a senior advisor to SADD, director of counseling and counselor training at Cape Cod Sea Camps, and a parenting expert at and NBCUniversal’s For more information about Stephen’s work, please visit

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