School Life

Ideally, a boarding school education is a partnership. The school, parents, and student comprise this partnership. What makes this relationship unique is that all partners must work together in the best interests of the student. In addition, each partner has a specific role to play and responsibilities to fulfill. Understanding those expectations is one reason families continue to see boarding school as a valuable educational investment in 2026.

Today’s boarding schools place even greater emphasis on communication, student well-being, and residential support systems than in previous decades. Many schools now offer expanded counseling services, structured residential life programming, and parent communication portals that help strengthen the partnership between home and school. Schools are increasingly prioritizing mental health support, digital wellness, and community-building initiatives.

School

Motivation

Obviously, the school wants the partnership to succeed for several reasons. First, student successes enhance the school's reputation. The academic marketplace remains highly competitive, and families have more educational choices than ever before. Parents conduct extensive research online, compare schools carefully, and frequently rely on both reviews and campus visits before making a decision.

As explained in The Future of Boarding Schools: What Parents Should Watch, boarding schools today are adapting to evolving parent expectations by strengthening wellness initiatives, residential life programs, and academic flexibility.

Schools such as Phillips Academy Andover, Choate Rosemary Hall, and The Hotchkiss School continue to expand wellness and leadership programming to meet the changing needs of students and families.

Contractual

The

This article has been updated to reflect 2026 data and recent developments.

At some point in your evaluation of boarding schools, you will examine the academics.

• You've done a bit of reading about the reasons for sending your child to a private school.

• Academics broadly include teaching style and philosophy, the number and depth of subjects offered, and curriculum.
• Let's discuss curriculum and specifically one of the most commonly used, Advanced Placement (AP), as it is known colloquially.

The Advanced Placement logo is a trademark of the College Board and it's in the Public domain, via Wikimedia Commons.

What is AP?

AP or Advanced Placement Program is a high school program offered by the College Board in 40 subject areas.

AP courses provide college-bound high school students with a level academic playing field. It doesn't matter whether you are a high school student in Dubuque, Iowa, or Darien, Connecticut, because AP courses and their end-of-course examinations follow common course frameworks regardless of where they are offered.

• The course content follows established AP frameworks.
• The teaching objectives are the same.
• The preparation for the final examinations is the same.

College admissions professionals can compare student academic achievements with confidence because the AP program provides common course and examination standards.

• They know precisely what AP means when they see it on your transcript.
• They know exactly what your AP scores represent.

That is the intrinsic value of AP Courses and their examinations from a

As you approach the end of high school, you might be considering whether to head straight to college or take a different path.

• For many students, the idea of diving into college right away can be daunting, especially given the significant investment of time and resources.
• If you're currently at a residential school, you might wonder if staying for an additional year or taking a gap year could be beneficial.

Your experience at a boarding school has likely taught you the importance of structure and community, which can be valuable as you consider your next steps.

• However, college campuses are often much larger and more open, which can present different challenges compared to the secure environment of your current school.
• Additionally, the transition to college life involves adapting to new academic demands, social environments, and personal responsibilities.
• If you're unsure about what to do next, staying at your school for an additional year or taking a gap year might be worth considering.
• Both options offer unique benefits that can help you prepare for college and beyond.

Let's explore these possibilities in more detail.

This TedTalk explains why everybody should take a year off before going to college.

A Post-graduate Year

Staying put in your present school for another year has several advantages. First of all, you know the school and its faculty intimately.

• A postgraduate year will allow you to explore your

2020-2021 have been unusual, depressing years as we all coped with the COVID-19 pandemic. Yet, notwithstanding all the gloom and doom, there was some good news in 2021. Several announcements of major gifts to private schools have lifted our spirits and given us, and the recipients, hope.

In October 2021, Berkshire School in Sheffield, Massachusetts, announced that an alumnus had left a bequest to endow three faculty chairs. Also in October, the Frederick Gunn School in Washington, Connecticut, reported that a current trustee and his wife had endowed a faculty chair. The munificence of these donors supports the stated mission of these schools.

The Berkshire School's mission statement notes:

"Rooted in an inspiring natural setting, Berkshire School instills the highest standards of character and citizenship and a commitment to academic, artistic, and athletic excellence. Our community fosters diversity, a dedication to environmental stewardship, and an enduring love for learning."

This video offers an overview of Berkshire School.

In its mission statement, The Frederick Gunn School states:

"In 1850 Frederick Gunn established a school based on the belief that strength of character was the goal of education. Today, The Frederick Gunn School rests on the four cornerstones of character: scholarship, integrity, respect and responsibility. Character is forged in a cohesive, diverse community informed by a challenging college preparatory curriculum, a broad range of athletic, artistic and social activities and

This article has been updated to reflect 2026 data and recent developments

2020 was a most unusual year. The coronavirus pandemic turned everything upside down and inside out. Nothing was normal. All of this impacted boarding schools in ways they never expected. While most private school boards of trustees were smart enough to have resumption-of-business plans in place and adequate insurance coverage for the school plant and the usual liability issues, very few school trustees ever expected to be dealing with so many challenges converging simultaneously.

By 2026, the immediate COVID-19 crisis has passed, but many of the leadership questions it exposed remain highly relevant. Independent schools are now managing enrollment uncertainty, affordability pressures, workforce shortages, technological change, and international enrollment challenges. The National Association of Independent Schools identified those issues among the complexities facing independent school leaders in its 2026 strategic planning work.

Against that backdrop, I thought it would be helpful to revisit this fictional interview with a head of school. After all, her concerns are probably yours as well.

What challenges at school keep you awake at night?

Rob: What challenges at school in the next academic year keep you awake at night?

Head of school: Oh, Rob! Where do I begin? There are so many things demanding my attention. My workday starts at 6 a.m. and ends at 10 p.m. if I'm lucky. And I work every day to keep my head above water.

Rob: What, then, is your most pressing