This article has been updated to reflect 2026 data and recent developments.
As your child enters middle school, you will probably begin to think more seriously about her high school and college plans. With that in mind, let's look at some of the challenges parents face. The whole subject is daunting, confusing, and even intimidating. However, if you approach the project just like you do any other major project or decision, you will be able to stay out front. Playing catch-up is never fun, so let's start planning early to understand what is involved.
Getting your child to buy into the idea
The first challenge is a basic one: you must get your child to buy into the idea of going away to school. Yes, you are her parent, and you can decide yourself. Unfortunately, this decision will do more harm than good unilaterally. The trick is to get her to think that going away to school is her idea.
How do you accomplish that? By starting early. Begin shaping her decision at least 3 to 4 years beforehand. If a family member currently attends boarding school, schedule a visit to see that relative while he is in school. The more comfortable your child feels with the idea of going off to boarding school, the happier she will be.
As she progresses through grades 7 and 8, she begins to discuss the academic game plan for high school and beyond. Sometimes, special considerations will make your decision process more manageable. For example, if your child displays a natural talent for a sport such as hockey or has musical gifts that you all agree need to be nurtured, then focus on boarding schools, which will permit him to pursue the rigorous daily regimens necessary to develop those talents fully. Certainly, by 9th grade, he will see the advantage of attending a residential school very clearly for himself.
Perhaps your child has special needs. Boarding schools can offer a consistent residential approach to supporting students with special needs, depending on the services available at each school. Tons of skilled supervision, teaching, and enormous positive reinforcement will make all the difference.
In this video, Alexis Avila, Founder and President of Prepped & Polished, offers tips on choosing the right private school.
Finally, you might want to try our approach. We were two professionals with busy careers living in the Litchfield Hills of Connecticut. Everything was miles away. Shopping, banking, after-school activities. Everything. Our daughter wanted to join as many groups as possible in her tiny public high school. After a year of becoming a taxi service daily, we convinced her that boarding school was the perfect solution. We got our lives back. We didn't have to worry about transportation and supervision. And, yes, it was her idea to go off to school.
Visiting schools
Visiting schools is a scheduling challenge more than anything else. You will have distilled your school choices to a shortlist of three or four. Now, you need to visit each one and experience the schools personally. Those school visits will make a lasting impression on you and your child and help you decide which school you would really like to see her admitted to.
Allow plenty of time for travel. Try to arrive the evening before your appointment so that both of you are relaxed and rested. You will have enough stress during your visit. You don't need the additional stress of arriving at the last minute or, even worse, late.
Take time to prepare your child so that she knows what to expect when asked questions. Your careful preparation and anticipation of what will happen will contribute to a positive experience for your child. That is very important for you to achieve.
Boarding School Review's Questions to Ask When Visiting a Boarding School (2026 Guide) offers additional guidance for preparing for school visits.
Preparing for admissions tests
You know your child better than any teacher. If she has gaps or deficiencies in her transcripts, fix those well ahead of time. That way when the official transcripts are sent your child's progress will be apparent. Admissions staff are much more forgiving when they see an issue has been identified and dealt with. You may have to hire a tutor to remediate a problem. Perhaps some extra practice is all that is needed. There are plenty of online resources to help you and her.
Once you have any issues dealt with, make sure your child works several admissions tests, if required by her chosen schools. At least one practice test should be timed just like the real thing. Again, none of this is difficult for you or your child to accomplish. You have to ensure that it does get done.
In 2026, admissions testing requirements vary by school. The Enrollment Management Association's SSAT guide explains the available testing formats and preparation options. Boarding School Review's Admissions Checklist for Boarding School Applicants also provides guidance on preparing for the admissions process.
Meeting all the deadlines
At the beginning of this article, I mentioned starting the school selection process when your child enters middle school, preferably in grade 7. The deadline you have been aiming for is the application deadline, which is typically the middle or end of January before the September school opening. If the school you are interested in has rolling admissions, try to get your application submitted before the Thanksgiving holiday. Submitting your application involves a major deadline that you have to meet.
There are other deadlines to keep on top of. Requesting transcripts, asking for teacher and principal recommendations, and registering for the standardized admissions tests are very important. Each task follows up and flows up, so factor that into your thinking. You cannot assume that anything has been done until you have confirmed that it has been done.
Application deadlines and testing requirements vary by school in 2026. The Enrollment Management Association's article on simplifying the application process discusses the Standard Application Online, which allows families to submit common application materials to participating schools. Boarding School Review's Using the Boarding Schools Admission Application Form provides additional practical guidance.
Paying for it
In many ways, how you plan to pay for your child's boarding school education has most likely been part of your discussions and planning from the beginning. Discuss financial aid with the school if you need financial assistance. Complete the financial aid application as soon as you have all the required documentation and data. In any case, do not be late submitting your financial aid request. Schools have a pool of money allocated for financial aid. Once it is spoken for, it is gone.
This video from OurKids offers some advice for paying for private school.
To sum up, none of the five challenges listed above are impossible challenges in themselves. They merely have to be thought about, discussed, and dealt with. Plan your work. Work on your plan.
