P.S. Don’t Forget About the Past

The article is co-authored by Crystal Land and Cecily Stock

“The date is July 14, 1978, the first day of our trip. I open my empty notebook, pull out my cheap Bic pen, and write the very first words…”(On the Hippie Trail, Rick Steves)

At L+D, we fully embrace planning for the future. In fact “optimistic futurist” is one the central tenets of our mission statement, and we consciously work to develop the habits and mindsets of futurists when we interact with schools on strategic plans, revised mission statements, new schedules and other institutional changes. But looking forward doesn’t mean ignoring the past, and taking a thoughtful look at a school’s history can be a powerful tool for shaping a vibrant, future-ready institution.

While we certainly don’t want to become overly focused on “the past” or wallow in “the good old days,” there are many benefits to learning and understanding from where we came as a lens for school leaders to work on needed and significant school changes. As we work with schools around the country, we’ve observed the challenges of frequent turnover of Heads of School, advancement/alumni officers and other long-time administrators –as well as the retirement of long-time teachers– all of whom are often the keepers of a school’s history. When these changes occur, institutions can lose the richness of the school’s stories, the nuances of a school’s history and often the essence of what brought them to their current time and place. 

As L+D continues our year’s journey on “curiosity,” how might we become more curious about what’s essential and important about a school’s past in order to also look forward to and better navigate the future?

First: Be an Anthropologist

Well-known travel writer Rick Steves revisits his origin story in the new book, On the Hippie Trail. Steves publishes his actual 42-year-old journal chronicling his 1978 journey from Istanbul to Kathmandu, with stops in Turkey, Iran, Pakistan, Kashmir, India, and Nepal. He says this book is, "a candid, unvarnished snapshot of our trip," serving as an artifact from a time when travelers navigated without the technology we rely on today: no websites to book lodgings, no cell phones or GPS to plot routes, and fewer resources for travelers who often woke up without a specific destination in mind.

Steves notes in the Preface, "And as if on an anthropological dig into my own past, I entered the world of 23-year-old me..." The book functions as a cultural artifact that allows readers to examine travel from a bygone era through the unpolished daily journal of a post-college budget traveler. What insights can we glean from this backpacking journey of days past? What wisdom lies within an old, scribbled journal? Why invest time reflecting on what was instead of what is or what might be?

By applying an anthropological lens to this era of travel, we can appreciate not only how these two young men physically traversed developing countries—on foot, via pedicabs, in overcrowded buses and trains -- but also how they approached their days with an open and exploratory mindset. They shared meals with local families, navigated communication barriers, endured stomach bugs, confronted their own cultural biases, and gained new insights into local customs, traditions, and religions. 

Although the "Hippie Trail" no longer exists (having closed in 1979 as many countries along the route sealed their borders), by examining this approach to travel—where daily destinations and outcomes remained largely unplanned—reminds us of the value of artifacts from the past like journals and old photographs. Using this approach with our own institutions, what might we learn from the “metaphorical journals and photographs” of key moments from our school’s past? 

Then: Honor Your School’s Past

With this in mind, how might school leaders dive into the past to gain an understanding of the school’s roots and identity? A good starting point is to consider the following essential questions as you engage in studying your community's history with an exploratory mindset:

• When does the “present” start in your school, according to most people? Why is that? (new head, new campus, post-covid)? What do community members actually consider “the past”?

• Who in your community holds deep knowledge or lived experience of the school’s earlier years? What parts of the school’s origin story can we study and share? Whose stories haven’t yet been heard?

• What might you be missing as you think about the current “present”?

• What do Boards need to know about the past to best understand a school’s history and culture so they can support the Head and the school’s direction?  

Cecily Stock, the incoming interim Head at The Presentation School (TPS) in California, is currently planning her entry into a new community this summer. As a seasoned Head of School with experience leading through major organizational change, she knows the importance of being curious and adopting an “anthropologist mindset” as she joins a new school. Preparing to go beyond the traditional, “listening tour,” she plans to engage in deep and sustained ways to learn about this school’s history so that she can best serve her new community.

Cecily suggests: ”As I prepare to join a new school, I find myself reflecting deeply on the importance of understanding and honoring a school’s past. In my experience leading schools through significant transitions I have found that meaningful and lasting change begins by genuinely exploring and respecting the history of a community. History isn’t merely nostalgic—it provides essential context.” As Seaman and Smith suggest in the Harvard Business Review , “leaders with no patience for history are missing a vital truth: A sophisticated understanding of the past is one of the most powerful tools we have for shaping the future.“ (HBR, “Your Company’s History as a Leadership Tool”). 

Guided by curiosity, here are some initial ways that leaders can honor the school’s past as they join a new community: 

Authentic and Broad Engagement:

To avoid missing important context for the School’s present situation, it’s crucial for leaders to immerse themselves fully in a new community to understand both explicit historical narratives and implicit cultural dynamics. Seeking out conversations not only with current faculty, staff, families, and trustees, but also, and as importantly: alumni, former Heads of School, and former trustees deepen this understanding. Engaging with newer community members can be helpful to identify gaps between the espoused history and culture and the “hidden curriculum” of the school.

Identifying Informal Leaders:

Perhaps one of the most important tools is to engage not only with individuals in formal leadership roles, but also its informal leaders: those individuals who quietly yet meaningfully influence the school. Observe who is frequently referenced in conversations or who exerts informal influence. Understanding their perspectives provides deeper insight into historical tensions, cherished traditions, and subtle cultural norms, enabling thoughtful and respectful navigation of future changes.

Respectfully Engaging Those Attached to Tradition:

Some of the most significant holders of the school’s culture may be wary of change. And yet, these individuals often hold deep knowledge and appreciation of the school’s traditions. By authentically listening and openly acknowledging the importance of their perspectives, leaders can build trust, reduce anxiety, and transform potential resistance into advocacy. Interacting with alumni both through more formal focus groups, as well as informal gatherings focused on strategic priorities can be a powerful way to honor their contributions and insights. Genuine engagement with those who value the past strengthens the collective ability to thoughtfully embrace future directions. As Harvard Business Review notes, “recalling history can unite and inspire people.”

Adopting the Participant-Observer Mindset of an Anthropologist:

Finally, immersing oneself in the daily life of your school—joining events, observing interactions, and spending time in the common areas on campus—is an effective way to deepen one’s understanding of both the school’s explicit traditions and implicit cultural dynamics. This is also a moment to maintain an awareness of one’s personal values and how they align with the school’s espoused values. Where differences arise—especially in areas targeted for potential change—be mindful of potential tensions, and maintain the exploratory state of mind vital for this work.  

Ultimately, an approach to leadership that begins by intentionally exploring and honoring a school’s history—both explicit milestones and implicit cultural norms—helps to build trust, inspire unity, and meaningfully prepare the community for successful and lasting change.

Finally: Try New Tools for Exploration

In addition to the approaches above, here are some additional ways that school leaders can facilitate an exploration of their schools’ histories: 

Time Travel: Go Back before you Go Forward (thanks to Jane McGonigal’s Imaginable) Take some time with any group on campus to practice some overt “time travelling.” Ask team members: Think back to the year–2010, 2000, 1990. Really imagine what it was like then. What did you wear? What was the technology like at that moment? What did the campus look like and feel like? How did the community gather back then? You might even search for old photos or video clips. Are there any special stories and people from the past that you need to know about, meet (if possible) and refer to in your understanding and telling of school going forward. The goal is to reflect on what is similar and what is different from then to now. What did you learn that can be integrated into the school’s “now”? Consider how many of these stories can be included in Board and New Faculty-Staff orientations. 

Create a visual timeline of the school’s history with the Board or admin team. Add in significant world events (COVID19, for example) and when each person joined the community. Use artifacts from the school’s archives or old yearbooks to add depth stories to the school’s history. What was it like before “you” were there? Build out the past as fully as possible and then ask this question: “What’s most essential from our timeline to understand the present moment?” Keep this up in a central place where you can add to it over the school year. 

Artifacts: This is an L+D favorite and for good reason. Ethnographic research provides leaders with deep insight into a school’s history as well as the present moment. Stories and artifacts evoke strong memories and stories. Just like Rick Steves’ journal, you might ask participants –alumni, parents, faculty–to bring a favorite artifact to a school meeting like the new faculty-staff orientation and reflect on what it tells you about the school and community. What themes and patterns emerge? How does understanding this history help me lead my area of the school more effectively?

Use interactive conversations regularly when planning events or preparing for a big change. This type of awareness allows planning groups to engage and reflect on the past in order to better plan for the future. An example is when preparing to change a revered event or tradition (school’s opening, step up events or graduation, Grandparents/Special Friends Day, the Spring Fundraiser, etc) start with some warm conversations prior to jumping into the actual planning and change: 

• Conversation 1: "What was an event you experienced when you felt a sense of deep connection and belonging?)? If you’ve been at the school for a while, what do you remember about the event you want to change that was memorable and resonant? 

• Conversation 2: Regardless of what we actually create or develop, what feeling do you want the community to be left with after the new event happens? 

Back to Hippie Trail

Rick Steves penned the journal that formed the basis of his book, On the Hippie Trail, 42 years ago and had not looked back at it in all of these years until recently. He notes that the trip served as a pivotal moment of change for him professionally as well, going from piano teacher to travel writer because of the experiences on this particular trip. His other insight: by paying attention to the past, “our world will be a more just and stable place.” That’s an optimistic and hopeful view–and one we might aspire to in our schools as well. In order to lead your community through significant change and embrace what may seem like a very different future, take a page out of Rick Steves’ book and dig into your history.