After decades in education, Estes Elementary School Principal Ryan Williams is preparing to retire from Owensboro Public Schools, closing a career defined by a commitment to students, creative leadership, and a school culture built on connection and fun.
Williams said the decision to step away was driven largely by family needs, as both his parents and his wife’s father face significant health challenges.
“My dad is in a nursing home over here. He’s got Parkinson’s. My mom drives 25 minutes each day, and I want to help her,” Williams said. “My mother-in-law died in January, while my father-in-law was diagnosed with pancreatic cancer. He’s on like day 70 in the hospital.”
Williams said he and his wife — who is also an educator retiring this year after 27 years — felt it was time to focus on caring for their families.
“So we’re both going out, and it’s time for us to take care of our parents the way that they took care of us,” he said.
While he is ready for the next chapter, Williams said leaving students behind will be the hardest part.
“All the students,” Williams said when asked what he would miss most. “Any teacher will tell you that. Any educator will tell you that you get in it for the students. But these students here — they’re a special group. They tug at your heartstrings.”
Williams said Estes has always focused on meeting students where they are and helping them succeed.
“We like to say we meet them where we get them, and we’ve always had to reach them before we teach them,” he said. “These students are a special group, and it’s going to be hard to relinquish this part of the job.”
That philosophy was shaped by Williams’ own childhood experiences in school.
He said he struggled academically from kindergarten through third grade before two teachers helped change his trajectory.
“I had two really great educators who took their time with me and poured into me,” Williams said. “I’ve always wanted to give back, because I’ve got a soft spot for students who struggle.”
Williams began his career teaching at Cravens Elementary from 1999 to 2012 before eventually becoming principal at Estes, where he worked to create a welcoming and energetic environment for students and staff.
Known for his playful and unconventional style, Williams frequently used creative incentives and schoolwide events to motivate students. Over the years, those antics included dressing up as Buddy the Elf during the holidays, appearing as Cupid on Valentine’s Day, and organizing themed assemblies and competitions.
“I always dressed up,” Williams said of his teaching days. “Sergeant Sounds, Mr. Prove-It, the referee — we had tag-team reading competitions.”
At Estes, the fun continued with karaoke lunches, pajama days, and Friday morning assemblies featuring awards like the “Estes belts,” “Top Dog” recognitions, and the school’s “Forky” dance celebration.
“We treat it like these kids put in the work, so they should feel a reward,” Williams said.
The festive environment also extends to the school’s holiday traditions. Williams said the building transforms each year with elaborate decorations and events designed to create positive memories for students.
“Christmas is big here,” he said. “For a lot of our kids, Christmas can be anxiety-ridden. So we go all out and decorate the front hallways with different scenes. We do a Christmas night here with Santa Claus.”
Williams said building a positive culture was a priority at Estes, both for students and staff.
“One of the great things that I treasure here is the culture that we’ve built, not only for the students but our staff too,” he said. “It takes special people. The work we do isn’t easy, but it’s so important.”
He noted the school serves a diverse student population with significant needs.
“One-fifth of our students see counselors. One-fifth of them are multilingual. Only 13 percent of our students this year came in ready for kindergarten,” Williams said. “But in saying all that, we don’t make excuses. We meet the students where they are and try to provide the best education that we can.”
Williams also credited his administrative team for helping shape the school’s success.
“You are only as strong as the people that you are with,” he said. “Without a strong team, you’re not going to go very far in this business.”
When it comes to advice for educators entering the profession, Williams encouraged young teachers to spend as much time as possible in the classroom.
“I would teach as long as you can, because this side is not as glamorous as what people say,” he said. “The money is definitely not worth it, and the stress that comes with this — you’ve got to have a great team around you.”
Although he plans to step away from education for a time, Williams said he does not expect to stay away forever.
“I need about six months to sleep and to make sure that I can be there to help my mom and my dad and my wife’s father,” he said. “Eventually, once we get our parents taken care of, I want to go back and do something in education.”
For now, Williams said he hopes the legacy he leaves at Estes is one of warmth and connection.
“School should be a safe, engaging place, and the students should want to be here,” he said. “That’s what I wanted to be known as — not a disciplinarian, but someone who could talk to students and explain. Everyone makes mistakes, but if you make the same mistake over and over again, it becomes a choice. And that’s what we don’t want.”
