Kelly Dickens: Living Authentically

Kelly Dickens faced a crossroads in 2006. His son Michael had enrolled at Headwaters the previous August, and Kelly was watching something unfold. “The school asked us—the whole family—to live authentically,” he explains. “My previous job offered financial rewards at the expense of self-expression. I could not tolerate asking my children to live their best lives if I was not living mine. So I returned to teaching.”

That September, Kelly joined the teaching staff. The following August, his younger son Joel enrolled. Both boys would go on to graduate from Headwaters, then The Khabele School, in 2012 and 2015.

Kelly came to Austin as a young man to pursue music and fronted a garage band called The Melcooleys. When rock stardom didn’t pan out, he enrolled at The University of Texas at Austin in the fall of 1985. To help finance his education, he launched a tutoring business, working with students in math and physics.

After earning a bachelor’s degree and teacher certification in mathematics, Kelly taught for Eanes ISD for a year before transitioning into actuarial mathematics—a field he worked in for 15 years while he and his wife, Linda, started their family. When it came time to find the right middle school for their oldest son, the Dickens family found their way to Headwaters.

What drew them was clear. “Small, child-centered, values-based, whole-child,” Kelly says. Those weren’t just words on a website—they were principles the school lived by.

Being both a parent and a staff member has shaped Kelly’s understanding of what families are really looking for. “Parents have many concerns—we don’t all share the same ones. But I believe we share a core desire for our children to be well, to be cared for and seen. If we attend to those concerns, others—discipline, pedagogy, policy—will be secondary.”

In his time at Headwaters, Kelly has taught a wide range of subjects, including Algebra I and II, Geometry, Precalculus, Math Applications, AP Calculus, Physics, AP Macroeconomics, Health, Personal Finance, and IB math courses. But for Kelly, the subject matter is secondary to something more fundamental.

“I believe the most important aspect of education is creating an environment where students can discover and develop who they are meant to be,” he says. “As our students navigate the challenges of school and growing up, I want them to know they are seen, they are heard, and they are absolutely all right. The personal connections we build are fundamental to our work. I am continually grateful that this school upholds that value—even if its impact isn’t easily quantifiable.”

When asked what he would tell prospective families about what makes Headwaters special, Kelly doesn’t hesitate: “From the top down, we value student experience and input. We have an intentional culture of acceptance and support. We value self-expression. We are a highly reflective staff and nurture student reflection.”

Outside the classroom, Kelly enjoys watching and reading about old movies—especially film noir—and diving into non-fiction books on a wide range of topics (not all math!). He also loves cooking, making up songs, and going for long drives with his wife Linda.

But his most important work happens within the walls of Headwaters, where nearly two decades ago, he chose to live the kind of life he wanted his children to see modeled. That choice continues to shape the lives of students who walk into his classroom, looking for someone who sees them, hears them, and believes they are absolutely all right.