In education, we navigate a world full of challenges, each one demanding creativity and perseverance. But some challenges are different – those that don’t fit neatly into categories or yield simple solutions. They’re not necessarily problems, crises, or opportunities—they’re just… tricky. You know the kind: situations with too many layers to unravel in one sitting or questions that don’t have a single right answer. When I hear someone describe something as “tricky,” my mind instantly goes to the iconic Run-D.M.C. song, It’s Tricky. If you’re already humming the chorus—“This beat is my recital, I think it’s very vital…”—you get it. Just like in the song, tricky moments require rhythm, effort, and a little bit of creativity to navigate.
So, what makes something tricky? It’s the layers. A tricky situation might involve balancing the needs of different students, navigating new technologies, or implementing a well-meaning procedure that not everyone fully supports. It’s the kind of challenge where the answers aren’t obvious, and sometimes you don’t even know the right questions to ask. Think about the first time we had to move to virtual learning overnight or tried to introduce equity-focused changes to deeply rooted and ingrained systems—tricky.
The beauty of the word “tricky” is that it reframes our mindset. Unlike heavier terms like “problem” or “crisis,” which can feel overwhelming, or even “opportunity,” which might feel overly optimistic, “tricky” sits in the middle. It’s a word that invites curiosity. It says, “This isn’t easy, but we’ll figure it out.” It’s nonjudgmental, leaving space for exploration, experimentation, and, yes, even failure.
Facing trickies in education requires us to lean on a few key strategies. First, curiosity over control. The best way to approach a tricky situation is with a willingness to learn. Instead of trying to force a solution, we can step back and ask, “What is this moment teaching us?” Second, collaboration over solitude. The best ideas don’t happen in isolation. When we come together, our collective creativity can turn the trickiest of challenges into manageable tasks. Finally, reflection over reaction. Trickies often tempt us to act quickly to resolve discomfort, but taking time to understand the complexity can lead to better, longer-lasting outcomes.
I’ve seen these strategies in action in my own work. A few years ago, we faced a particularly tricky challenge: how do we balance the populations at various elementary and secondary schools with minimal disruptions. We didn’t solve it overnight, but by involving students, families, and educators in the conversation, we started to chip away at it. The solution wasn’t perfect, but the process taught us how to listen, adapt, and build trust.
Trickies are part of the terrain in education—they’re not detours from the work but central to it. They stretch us, challenge us, and, when we embrace them, make us better at what we do. The trickies push us to innovate, to think more deeply, and to grow as a community.
So, the next time you encounter a tricky, channel your inner Run-D.M.C. Remember that it’s not just about surviving the challenge but finding the rhythm, leaning into the process, and maybe even enjoying the ride. “It’s tricky to rock a rhyme,” but as the song reminds us, tricky doesn’t mean impossible. Let’s embrace the trickies.
Thanks to my colleague Ian Kennedy, a seasoned educator and district leader for modeling how to embrace trickies with curiosity and resilience, and to the Roy Group for guiding our administrators in managing these complexities.
Of course, now Ian knows I have Run DMC running through my head every time he talks about the trickies.
The image at the top of the blog was created in Chat GPT 4. Some of the research around Run DMC and their song “It’s Tricky” was based on a series of prompts in both Chat GPT 4 and Claude.