A Strategic Vision Forward Middlesex
Expanding the Circle PATHWAYS TO PROMISE
From the Head of School
ON BEHALF OF THE MIDDLESEX STRATEGIC VISION COMMITTEE, we are delighted to introduce Expanding the Circle: Pathways to Promise, a strategic vision to lead Middlesex forward by investing in our most cherished and invaluable resources: our people, our place, and our program. This Strategic Vision integrates both traditional and innovative approaches to education, equipping our students with the skills and agility they need to thrive as lifelong learners and leaders at Middlesex, in college, and beyond. The 2002 Strategic Plan called for Middlesex to become a “premier, small, national boarding school.” Pathways to Promise now calls for us to distinguish ourselves as a leader among that group of peer schools by leveraging our unique strengths, investing strategically in our people, place, and program, and “expanding the Circle” in a rapidly evolving world.
Throughout the process of creating this vision, we remained true to our founder Frederick Winsor and the first board of trustees’ mission to “find the promise” in every student and to ensure that each Middlesex graduate would be “imbued with the spirit of democracy” through the open exchange of ideas. Finding this balance was, ultimately, our primary charge: to build a strategic vision that is ambitious, dynamic, and forward thinking, while also rooted in the School’s history, mission, and core values.
Expanding the Circle: Pathways to Promise seeks to enrich Middlesex’s rigorous and close-knit learning environment through academic and community initiatives that foster curiosity, integrity, joy, confidence, humility, hard work, connection, and civic responsibility among our students. Core tenets within this plan include:
From the Head of School
• Expanding Middlesex’s role as a leader in education through a commitment to academic experiential learning, deepening student engagement with the world beyond our Circle;
• Ensuring that we are responsible stewards of our beautiful campus, equipping students with the skills and optimism needed to find solutions to environmental challenges;
• Strengthening and building upon the pillars of our distinctive academic strengths—most notably the remarkable talent and dedication of our exceptional faculty—and prepare our students with the essential skills they will need for success beyond Middlesex.
Pathways to Promise is guided by the core belief that education should broaden students’ capacities in critical reasoning, empathy, independent thought, and respectful discourse, and that Middlesex is uniquely suited to foster these skills exceptionally well.
I am deeply grateful for the leadership of Trustees Courtney Portlock P’20’22 and Rob Trumbull ’00, who co-chaired a Strategic Vision Committee composed of faculty, students, trustees, alumni, and parents. I also want to extend my immense appreciation to each member of the committee who met regularly over the course of a year to craft a thoughtful and ambitious vision for the years ahead. Their work, recently approved by the Middlesex Board of Trustees, reflects the voices of our community, our insights from extensive research, and a steadfast commitment to our mission, which itself has been rearticulated more concisely as part of this process. The communal energy devoted to this visioning effort was inspiring and notable. We are so fortunate to be part of a school community committed to the hallmarks of a Middlesex education and unafraid to dream of all that is possible for this exemplary institution.
Sincerely,
Elizabeth C. Speers Head of School
Mission
Middlesex School helps students find their promise through rigorous intellectual, physical, creative, and ethical education. We value integrity, kindness, inclusivity, excellence, and engagement in service of our community and the wider world.
Guiding Principles
Excellence and Innovation
This plan aims to pursue high standards and innovative approaches to education that prepare students for future challenges and opportunities. We affirm that:
• A Middlesex education is defined by a rigorous academic program that fosters curiosity, critical thinking, and deep engagement with ideas, guided by talented and dedicated teachers in small, interactive classes.
• A Middlesex education is defined by the premise that academic excellence happens best in a diverse community.
• A Middlesex education is defined by a holistic approach to learning that includes immersive experiences across academics, arts, athletics, and community life, preparing students to adapt to new experiences and technological advancements for success in a changing world.
Community and Inclusion
This plan aims to foster a supportive and inclusive environment that strengthens the sense of belonging for students, faculty, staff, and families. We affirm that:
• Middlesex best serves its mission through a close-knit residential community that cultivates meaningful interpersonal relationships.
• Middlesex is made stronger by the broad spectrum of belief and experience each of us brings to the School.
• Middlesex is committed to community and inclusion as an integral part of the mission, woven through all areas of the School.
Citizenship and Stewardship
This plan aims to advance the stewardship of democratic ideals, civic responsibility, and environmental sustainability. We affirm that:
• Middlesex seeks to cultivate a sense of civic responsibility that honors democratic ideals and embraces respectful debate.
• Middlesex seeks to cultivate a sense of place that inspires stewardship and appreciation of the natural world.
• Middlesex seeks to cultivate a sense of global stewardship that is grounded in curiosity, connection, and impactful engagement with communities locally and abroad.
STRATEGIC PRIORITY
Invest in Faculty and Staff
Strengthen Compensation, Benefits, and Wellbeing
• Ensure competitiveness of total compensation packages through regular review and growth of faculty/staff compensation and benefits, with a focus on expanding housing options for faculty.
• Develop policies that prioritize faculty and staff wellness, balance, and job satisfaction.
Foster Professional Development
• Invest in ongoing professional development opportunities, including workshops, conferences, and collaboration with external institutions.
• Establish mentoring networks that promote career growth and leadership within the faculty and staff.
Cultivate Belonging
Enhance Community and Inclusion
• Foster a diverse and inclusive community through a plan with programs and policies that promote belonging for all students, faculty, and staff.
• Increase diversity of faculty and staff.
Develop Character, Citizenship, and Wellbeing
• Strengthen commitment to mindfulness, ethical training, civic responsibility, and service learning.
• Promote healthy, face-to-face interactions while integrating technology thoughtfully.
Revitalize Campus Spaces
Elevate Learning and Living Spaces
• Update classrooms, dormitories, and common areas to create flexible, collaborative environments that support learning and community building.
• Prioritize essential campus repairs and upgrades through a comprehensive campus master planning process that ensures a safe, functional, and accessible campus for all.
Strengthen Athletic and Outdoor Facilities
• Renovate and expand athletic spaces to support physical fitness, mental health, and wellbeing for students and faculty alike.
• Reimagine outdoor areas to promote connections with nature, encourage collaboration, and create opportunities for recreation and active learning.
Commit to Environmental Sustainability
Prioritize Sustainability in Resource Management
• Establish measurable goals for reducing the School’s carbon footprint.
• Emphasize sustainability when sourcing and planning for future campus improvements.
Foster Environmental Stewardship and Leadership
• Develop an integrated environmental curriculum that encourages student-led eco-initiatives, considers disparate ecological impacts, and fosters a campus-wide culture of sustainability.
• Embrace our proximity to the Estabrook Woods and Walden Pond through programs that deepen students’ ecological knowledge, stewardship, appreciation, and sense of place at Middlesex.
STRATEGIC PRIORITY
Program
Enhance Excellence and Innovation
Cultivate Engaging and Adaptable Learning Experiences
• Develop opportunities for experiential learning.
• Infuse more flexibility into a student-centered learning experience that promotes joy, engagement, and curiosity.
Build Skills for Intellectual Agility and Discourse
• Equip students with essential skills like collaboration, communication, and adaptability to prepare them for evolving societal, environmental, and career challenges.
• Launch initiatives that foster critical thinking, intellectual engagement, and active discussion on democracy and civic engagement.
Expand the Circle
Broaden Global and Local Learning
• Increase study abroad opportunities, fostering a global perspective and cross-cultural competence through domestic and international travel.
• Integrate the School’s unique geographical and historical context into the curriculum.
Strengthen Community and Alumni Connections
• Build partnerships with local organizations, providing students with meaningful opportunities to give back and develop leadership skills.
• Leverage the School’s strong alumni network to offer new learning experiences, career connections, and mentorship.
The Strategic Vision Committee
Committee Chairs
Courtney Portlock P’20’22, Trustee
Rob Trumbull ’00, Trustee
Members
Dan Barber, Head of Classics Department
Johanna Boynton P’20’23, Trustee
Marc Carter, Chief Innovation Officer
Caroline Counselman P’25’28, Trustee
Therese Ejiofor ’24, School Co-President
Ty Fein ’24, School Co-President
Bill Ho ’86 P’23, Trustee
Mandy Irwin, Biology; Environmental Science
Tom Kane P’18, Head of the Arts Division
Olivia Kennedy, Assistant Dean of Students; English
Eric Kester ’04, Assistant Head of School; English
Natalie Martinez P’26, Associate Director of College Counseling
Stacey McCarthy P’28, Head of the Visual Arts Department
Meg McLaughlin P’20’21’25, Director of Health and Wellness
Karlyn McNall P’21’23, Associate Head of School; History
Doug Price P’16, Dean of Admissions and Financial Aid
Mike Rivetts, Facilities Superintendent and Grounds Foreperson
Alex Hanken Russell ’08, Trustee
Rebecca Smedley, Director of Spiritual and Ethical Education; English
Jason Sport, Chief Officer for Diversity, Equity, and Inclusion
Bret Stephens ’91 P’22’27, Trustee
Pierson Wetzel P’26’28, Head of the Music Department; Dean of Hiring and Recruitment
Ex Officio
Jason Robart ’83 P’11’13, Chair, Board of Trustees
Bessie Speers, Head of School