Cynthia Bailey, principal of Hillside Elementary in the Westside School District, has a bachelor’s degree from Stanford. She also has a handful of advanced degrees in education, including specialized training in teaching English language learners. She is considered by her peers and supervisors to be an excellent, dedicated educator.

She has also cut songs professionally, in studios; she was a backup singer for Engelbert Humperdinck; and she is trained in ballet.

At first glance, the connections seem unlikely.

“I believe that people are limitless in what they can do,” Bailey explained.  “I feel like we limit ourselves. We say, ‘OK I have to choose a career path.’ But I don’t do that. I believe in finding what you are passionate about and then going for it. It’s something I call choosing your hot track.”

The phrase ‘hot track,’ Bailey said, is language she adopted from conversations with her friend Patricia Tallman, a longtime friend in Los Angeles who organizes life retreats meant to inspire and energize people. Bailey said that this term is a good description of the philosophy she applies to everything she does. The goal is to be passionate.

This passion has earned Bailey high praise from fellow educators. Dr. Mark Weichel, the assistant superintendent of Westside in charge of teaching and learning, said, “Cynthia is a fantastic educator. What makes her stand out is that not only is she an expert in her field, but her passion for caring about students and her staff is amazing.”

“She’s funny, too,” Weichel continued. “She’s great to have in meetings.” Bailey refers to her time performing in dinner theater as “slipping on broccoli.” Bailey has short hair and green eyes, and doesn’t “have” energy, she emits it.

Bailey was born and raised Dallas. She finished her last couple years of high school in Southern California, and earned a scholarship to Stanford. She was a ballerina at the time.

After she graduated from Stanford with a degree in broadcast journalism and communications, she decided to follow her first passion.

“After I finished college I went to L.A.,” she explained. “I had a degree in broadcast journalism, but I had done so much theater, and loved it, that I said I’ve got to follow this hot track.”

As an entertainer, Bailey did it all, from performing in plays at the Westwood Playhouse to doing shows on cruise ships to doing voiceovers for animated shows. She earned her SAG card.

She was briefly a singer for Engelbert Humperdink, which she said sounded more glamorous than it was.

“The entire band traveled the country on a tour bus a great deal of the time,” Bailey said. “If you’ve never lived on a tour bus, it is quite the experience. You finish your gig, you board the bus, spend some time with your bandmates, head to your bunk, and then you wake up in the next city. Half the time I didn’t know what city we were in—and it didn’t matter that I didn’t know. All the arenas and theaters start to look the same. It was an interesting way to live. You get really close to the people you’re working with. Sometimes Engelbert would travel with us on the bus. He had a bedroom in the back. Sometimes he would fly to the next gig, and we would go by bus. I actually preferred the bus. It was easier.”

She enjoyed being an entertainer, but then she had a child with her husband at the time. This was a turning point. 

“I couldn’t travel anymore. I kinda didn’t want to. So I had to figure out what I was passionate about now. What I found was teaching. It was a perfect fit for me.  I loved teaching.”

She began her career in L.A. after earning her degree in cross-cultural language acquisition, teaching English language learners in some of the toughest schools in California. She divorced her then-husband. She learned a lot.

Then, she fell in love with Andrew Bailey. “I met this Nebraska boy. He’s so awesome,” she said.

They moved to Nebraska, and at first she tried to lean into domesticity. “I thought, ‘great. I can just raise kids and stay at home.’ I lasted five months.”   

She couldn’t stay away from her passion for teaching, so she went hunting for jobs. “I called Millard, and said I liked Title I schools,” Bailey said. Title I schools are those that receive supplemental funds due to large concentrations of low-income students. “I fit in at Title I schools. I understood Title I schools. They had one position, they offered it to me. I took it.” She served as a reading and math interventionist for six years in Millard, and then for four more years as a teacher leader.

Then she went to Westside as a principal. She said Hillside is a perfect fit for her. “I only want to be a principal in a very diverse school. That’s my thing,” she said. “I love it here.” >

For Bailey, being a good educator means looking at the whole person, whether dealing with students or staff. Regarding students, she said, “You have to look deeply. You have to understand the kid, and the circumstances, and what they’re bringing to the table. You can’t be a surface dweller. Some of the kids who love us the most show us in the most unloving ways.”

Bailey also believes in involving community. “We have to go deep in education,” she believes. “While I believe in test scores, I am really looking at the entire child. I consider things that aren’t as tangible. Is there parent involvement? Do kids love the experience? We do lots of things here that engage the whole community.”

Her passion for music led her to be a key researcher and developer of a program that provides free music instruction to student who could not otherwise afford it.

“I am not just educating a child,” she said. “We do one school, one book. We have a community club that is very active, we have lots of ‘nights’ like STEAM Night (short for science, technology, art and math) and Literacy Night. We are there for the whole family.”

Bailey is also very aware of the challenges that face educators. She thinks that one of the biggest challenges they deal with is the screen-based world children live in. “If I had a message for parents, it’s that I want them to know that the way the world is, does shape their child. I am of the opinion that a lot of this technology we have is affecting children’s lives. Kids are not allowed to unplug and really just have space. They need space to create thought.”

This understanding is why Bailey is a metro-wide leader in mentoring student teachers. Hillside often has four to seven student teachers working there each semester.

Besides passion, there is another key to success that Bailey maintains is important, regardless of the career: perseverance. “I don’t always say the right thing,” she said, “but I believe that the thing that defines a person is, do they hang in there?  They learn, they learn, they learn. And I am going to hang in there.”

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This article was printed in the March/April 2019 edition of Omaha Magazine. To receive the magazine, click here to subscribe.