Greg MacGilpin, Jr.

About Me

I currently lead a PK-12 IB school in Puerto Rico 🇵🇷 and serve as the president of the Caribbean Association of Independent Schools (CAIS). I started my career as a kindergarten teacher, learning from the beginning that children learn when they are curious and when we, as adults in their lives, meeting them where they are. My goal is to instill confidence in all of the school’s constituencies, to encourage us to take risks, to leap far and often. I seek to shape school cultures for students to become actively involved in their own learning while discovering the rewards and satisfaction of hard work.

My Interests

I loved hiking the mountains of Lebanon. I am not an advanced, technical rock climber, but I learned their terrain and have years of experience outdoors; their rugged, untamed nature pulled me as often as I could get away from Beirut. At any given moment, you are walking along similar territory as Syrians, Mamluks, Romans or Phoenicians, and, in many cases, with the same minimal guidance as they had over a thousand years ago. There are limited signs and footpaths between the villages, and wherever there are markers, they serve as more of guidelines than ‘must-follows’, in the form of landmarks or crude cairns. I have been reflecting on this experience as I lead schools these days, for the pathways and markers towards a predictable and successful future seem to be less and less clear. Which leads me to think that, for our graduates to transition to young adulthood, they need adults in their lives who can help them to be safeenough, to be skilled enough, to be resilient enough, to know how to navigate the woods or the mountains or the world ahead, knowing they may not have clear markings to help them where to go, but they will be able to end up either where they hope to be, or somewhere they had not imagined possible.