Gratitude Tour: Trip Darrin

During my twenty-six years at Blue Ridge School, I worked for four heads of school.  Ed McFarlane hired me.  He was followed by Dave Bouton, then John O’Reilly.  In my final and (I would say) most critical twelve years at BRS, Trip Darrin was Head of School.  As I began to ponder how I might remain relevant in my waning years, Trip, time and time again, believed in my abilities to adapt to an ever-changing landscape.  He also supported my exploring new opportunities in and out of the classroom.  In my final year, he gave me multiple opportunities to speak to the students, the faculty and the Board.  He appreciated whatever wisdom I’d acquired over the years and gave me opportunities to share that wisdom with the Blue Ridge School community.  I will be forever grateful for his leadership and, more importantly, his caring for me.

Trip was hired as Director of Admissions at Blue Ridge in 2006.  His wife Karen Fink taught ESL that first year.  Since I was Alumni Relations Director at that time but also an English teacher, I came to know them both fairly quickly.  My wife Merf got to know Trip, too, in 2007 while in New York on business, she for CFA, he for the school.  She met Trip and Rob Murphy for dinner.  Apparently, both of them had eaten a great deal of bread before their steaks arrived that night.  She, who had eaten no bread, and Rob, who had eaten the same amount of bread as Trip, downed their steaks with no issues.  Trip, however, could not eat his entire steak, which gave Merf an opportunity to bust his chops.  This story would become a running joke among us, and Merf has been busting Trip’s chops in one way or the other ever since.  

I indirectly delivered to Trip a four pack of twelve-ounce Dragon’s Milk Bourbon-Barrel Aged Stout the night before I met him on September 4, 2025.  I relied on Simon Curry to deliver the beverages at a later date so that I wouldn’t make the hand off during the school day potentially in front of students.  

I had not been privy to the details of Trip’s ascension to Head of School in 2012.  The account he gave me during our visit was fascinating.  Most remarkable was how close he came to being fired not too long after he became Head of School.  Trip took a significant risk in challenging the Chair of the Board at that time because he was passionate about maintaining and even increasing diversity in the student population by making financial aid available as much as was sustainable for the school.  In my twenty-six years at Blue Ridge, I witnessed the increase in diversity and considered it one of the strengths of the school.  Trip had already written a lengthy letter to the Board.  The day that Trip addressed the Board on this important topic, he emotionally made his appeal that financial aid is, and had always been, a bedrock component of the Blue Ridge mission.  It was a tense moment in Trip’s career.  He and Karen had already discussed the very real possibility that he could be out of a job after the Board session.  Thankfully for the school, he wasn’t, and the Board affirmed the strategic deployment of financial aid as an essential part of fulfilling the mission to educate and raise young men of character. Trip’s willingness to stand by his values and to speak his mind even at the risk of his career made me admire him even more than before.

During our visit, he made the point that my love and loyalty for Blue Ridge School had likely been formed before he arrived.  He was correct, but I reminded him that I stayed at Blue Ridge for those last twelve years because of his support of me and my admiration for him in the face of great adversity.  In 2020, when COVID turned the educational world upside down, he was instrumental in keeping Blue Ridge afloat.  I and many others in education considered leaving the profession during COVID.  It was truly a difficult time.  Trip found ways to keep me and others in the game.  

Also, my time at Blue Ridge would likely have been one year shorter if not for Trip, who went out of his way to find housing for me on campus.  Merf had already taken a job in Annapolis, MD, in 2023, and I literally had no home in Virginia.  I will always cherish living in shared housing with three up-and-coming educators during my final year at Blue Ridge.  Trip has continued to explore ways to keep Blue Ridge viable while remaining true to its mission.  I think I was able to convince him that he more than deserved a beverage as my token of appreciation.  When I mentioned The Greatest Beer Run Ever as my inspiration for the beverage delivery, he snapped a picture of the front cover of the book to share with his dad, who served our country during the Vietnam War.

After graduating from Wahconah Regional High School in Dalton, MA, in 1987, Trip earned his BA in Political Science from George Washington University in Washington, DC, in 1991.  He also completed some graduate coursework in Japanese at Monash University in Melbourne, Australia. Trip admits this was more an excuse to travel than to study.  Trip’s uncle, who was born in Japan and had migrated to the US, inspired him to teach in Japan.  That’s where Trip began his career in 1994 as an English teacher.  “I was in WAY over my head and was a ball of nerves on my first day.  Thankfully, I was team-teaching with a Japanese teacher, and she helped calm me down!”  His journey as an English teacher took him to eleven different middle schools in rural, northern Japen until 1997.  After that, he served as a policy analyst for the Japanese Department of Science, Technology and Education.  

In 2000, Trip attended a party at the Japanese Embassy in Washington, DC.  Karen was there, too.  She caught his eye, and a conversation commenced.  Karen had just returned to the US after teaching for two years in the same program that had employed Trip.  They had that and much more in common.  Trip credits Karen for inspiring him to return to participation in schools when, at the time, he was pursuing a career in foreign service.  With Karen now by this side, he served as Director of Admissions and Financial Aid at South Kent School in Connecticut until 2004 while Karen taught ESL (now commonly called ELL).  

During that time, Trip was in touch with Rob Murphy, then Director of Admissions at Blue Ridge, since the two schools were often interested in the same students.  After working as the Director of Admissions at the Luanda International School in Luanda, Angola, in western Africa from 2004-2006, he and Karen once again were seeking positions in the US so he called Rob.  In a stroke of good fortune, Rob had just been named Director of Advancement so the Admissions position at Blue Ridge was available.  

Andy Vadnais, who was Head of South Kent School when Trip was there, encouraged Trip to pursue independent school leadership. Since 2006, Trip has served Blue Ridge first as Director of Admissions and Financial Aid until 2008, then as Assistant Headmaster until 2010, then Associate Headmaster until 2011, then Acting Headmaster until 2012, and now Headmaster for the past fourteen years. Trip is grateful that BRS made it possible for him to pursue his Master’s of Business Administration at the University of Virginia’s Darden School of Business.  Trip is now in his twenty-eighth year in education and has no plan to leave Blue Ridge anytime soon.  

The spark that has kept Trip going all of these years is first his family.  He and Karen have raised two children on the Blue Ridge campus, a daughter who is now in college and a son who is now a student at the school.  “Our community bonds strengthened in amazing, unexpected ways once Karen and I had children.  We feel that raising them within the BRS community has been one of our greatest blessings.”  Trip’s humility prevents him from being swept up in grandiosity, thinking he’s changing the world, but of course he is as are all educators.  Instead, he focuses on the small differences he’s making for good by being part of Blue Ridge School’s mission.  “I get affirmation that our mission is important every time I attend the BRS graduation.  Watching the boys jump into the lake is a symbolic launch of young men of character out into the world.”    

In addition to those already mentioned, Trip would visit many others on his own gratitude tour.  He’d start with his parents, his brother and his grandparents (if they were still alive).  He’d also say thanks to his “sensei” and host family in Japan.  He’s grateful as well for Ed Kowalchick, who was a good friend and mentor.  That day he spoke to the Board and afterwards, he found support from Mike Boswell, Dickie Brawley, and Mitch Rue. Trip’s gratitude extends to other Trustees, BRS leaders, and alumni who have helped him grow in leadership and grow in his love of Blue Ridge School, including people like John Joseph, Ben Hiatt, Jill Kalinski, Jimmy Crocker, Robb Sasser, and Franklin Daniels. He hopes he has given each of them a proper thank you.  He’s immensely grateful, too, for the strong current Board leadership of Sharon Rymer and David Townsend.     

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Trip is concerned that schools of all types and sizes have become too customer-focused, probably for market-driven, economic reasons.  “When this occurs, the delivery of education becomes more about placating students and their parents, and less about real depth of learning.”  He recognizes that it’s a societal issue and that politicians would likely risk their livelihood to exact some of the necessary changes.  On a smaller scale, the stronger a school becomes in its financial underpinnings, the more independence it gains from these pressures.  My interpretation of this from a teacher’s perspective is that students need to be presented with challenging situations in which they might fail.  Significant learning occurs from such challenges and from failure.  Both students and their parents need to accept that as a critical part of education.     

Trip recalls many mistakes (a form of failure) he has made in his career.  As a head of school, he knows it’s important to acknowledge his errors and, through his actions, communicate that it’s okay to make mistakes.  He says, “If you don’t make them, you’re probably not trying hard enough or not getting out of your comfort zone enough. I believe very strongly in the power of learning from experience; learning through trial & error.”  Again, my interpretation of this is that society needs to accept that students learn best through trial and error.  If schools are put in positions to placate their customers at all costs, then the students are likely not receiving the education they so desperately need.  

One mistake that Trip recalls was failing to appreciate the level of harm that a student was causing others.  He made the decision to give that student one more chance. Another student had the courage to visit Trip in his office and tell him he had failed the Blue Ridge community with his decision.  He was right.  “I have tried very hard ever since to balance the interests of individual students alongside what’s best for the whole community when facing decisions on expulsion.”

I’ve mentioned that Trip steered Blue Ridge through the pandemic and post-pandemic years.  He considers that one of his greatest successes, rightfully so.  Enrollment declined in boarding schools across the nation.  Blue Ridge achieved full enrollment just a couple of years after the pandemic ended.  He’s also proud for restoring a sense of what he calls “pride of school” within the student and alumni bodies.  He has recently helped launch the biggest financial campaign in the school’s history.  So far, so good!  His greatest source of pride, though, comes from seeing his son become a Blue Ridge boy. 

When he considers parts of his job he doesn’t agree with, he can’t think of many because he found a school community in Blue Ridge where he feels connected to its mission, culture and values.  This is his most important advice he would give to young educators.  “Teach in a school in which you can fully support what it’s trying to accomplish.  You may not be completely happy with every policy or decision, but, if you believe in that school’s mission and can thrive in that school’s culture, you will have a successful, fulfilling career.”  Trip, does, however, mention parts of his job that he doesn’t like.  He never enjoys expelling a student or disciplining an employee.  In such instances, he tries not to be formulaic.  Instead, he contextualizes his decision or course of action based on the individual.  I mention in my “Last Lecture” a matter involving one of my advisees in the final days of his senior year.  I was witness to Trip’s empathy and care for that student as he explained why and how he would be disciplined.  On that day, Trip was real to that young man.    

When my wife spent that evening in New York with Trip and others, she told me that Trip was easy to talk to, very down to earth.  That was true as I had already come to know when he served as Director of Admissions and Financial Aid.  At that time, I viewed us as equals.  I am the one who is guilty of changing my perspective when he was named Head of School.  Suddenly, he was my boss.  Trip’s perspective never changed.  In fact, I recall his saying to me one day not long after he’d been named Head of School, “Dan, I’m still me.”  He’s definitely himself in everything he does.  He’s certain that’s how the students he taught and the many students who have been at Blue Ridge under his leadership would describe him.  He was absolutely real that day he spoke to the Board at Blue Ridge about the importance of financial aid.  He’s been real to me dozens of times when I’ve needed a friend more than I needed a Head of School.  For that, I’ll be forever grateful.  

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