The Courage of a Maybe | Hooray For Monday

September 1, 2025

By Aleta Margolis, Founder and President

Listen to this week’s Hooray For Monday podcast for the audio version of this week’s newsletter.

Students in Washington, DC on the first day of school, with members of the National Guard in the background. Photo by Jose Luis Gonzalez/ Reuters via The Associated Press.

Things are changing at a breakneck pace in our country and in our communities.

Here in DC the National Guard is deployed in our city streets. And it’s likely this will happen in other cities in the near future. What does this mean for us and our students? What questions will students have about their city, and what will we say when they ask us?

AI is finding its way into curriculum and instruction. Will AI enhance learning? Will it replace teachers? Will it erase critical thinking? (More on that soon!)

Not to mention the “normal” uncertainty that comes with the beginning of each school year as students wonder, “What will my teachers be like? Will I have the same friends as last year? How will I get all my homework done?” and more.

As we get the school year off and running, it can be tempting to hunker down, focus on academics, and try to avoid our students’ questions about the uncertain times we’re living in. And if we expect ourselves as teachers to offer certainty in response to our students’ questions, then it makes sense that we’d try to avoid them.

So, if we’re not going to avoid students’ questions, and we recognize we can’t offer certainty, what can teachers do?

We can build uncertainty tolerance.

Inspired Teachers know that school is a place where young people learn to navigate the world around them. And that means navigating uncertainty.

If you know Inspired Teaching, you know that our approach to teaching and learning is based in improvisation. That’s been the core of our work for 30 years. Improvisation increases uncertainty tolerance—our capacity to stay well and focused, amid the unknown; it enables us to thrive even when things don’t turn out as planned. Improvisation helps teachers, school leaders, and students set and achieve ambitious goals while embracing the surprises that show up along the way.

Inspired Teaching’s Speak Truth programming provides strategies and activities for teaching high school students how to engage respectfully when tackling tough subjects.

Here are some things you can do at the start of the year, and all year long, to incorporate improvisation into your classroom, and build uncertainty tolerance for your students, and yourself:

Emotion Continuum

An important component of uncertainty tolerance is emotional regulation. This activity helps students—and teachers—identify and understand how they’re feeling.

Hot Takes

This activity supports active listening as a key skill for understanding and collaboration. And it teaches students to engage their curiosity and ask thoughtful questions of their peers.

Making Re-Solutions

Uncertainty has always been with us. That means there has never been a problem that couldn’t benefit from a fresh perspective. This activity uses existing issues to help students think more deeply about problem solving in general.

In her book Uncertain: the Wisdom and Wonder of Being Unsure, journalist Maggie Jackson points out that in his iconic “I Have A Dream” speech, Martin Luther King was wise enough to put forth a vision of the future that acknowledged the many unknowns, and clear-eyed enough to know that navigating those unknowns required group effort.

Jackson argues that Dr. King was saying, “We cannot find the best path forward…by assuming that we already know the way,” and that he “responded to the vehement yeses and no’s of the moment with the courage of a maybe — the only call to action that fully confronts the unknown.”

This is our call to action as teachers of young people: to model the courage of a maybe, to teach our students to navigate the unknown, and to stay curious all along the way.

For additional insights, resources, and information on Inspired Teaching teacher and youth programming, subscribe to the Hooray For Monday newsletter!

Hooray For Monday is an award-winning weekly publication of Center for Inspired Teaching, a social change nonprofit organization that champions the power of curiosity and is dedicated to transforming the school experience from compliance-based to engagement-based.​ Inspired Teaching provides transformative, improvisation-based professional learning for teachers that is 100% engaging – intellectually, emotionally, and physically.

Listen to This Week’s Episode of Hooray For Monday