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Alli Skibbie ’08 (right), puts her educational skills to work in an unforeseen context.

Alli Skibbie: A Teaching Vocation, Country-Style

As Alli Skibbie ’08 begins a teaching job this month in New York City, she brings along a lot of varied experiences to the classroom – the latest of them working as a nanny for a Grammy-winning singer and songwriter.

“It’s definitely been a journey,” said Skibbie from her New York apartment after a morning orientation at a Success Academy Charter School in Harlem. “It’s important for me to get back in the classroom.”

Skibbie majored in English and Spanish at St. Norbert. “I knew I wanted to be a teacher, but I also wanted to study abroad and I just couldn’t get both done,” she said.

After college, she worked for a year at a credit card company before signing up for a program in Los Angeles that helps students earn their teaching credentials if they volunteer on different projects. The program was demanding as Skibbie volunteered and took the necessary classes to earn her master’s degree in education from Mount St. Mary’s University.

With her teacher’s certification in hand, she then spent four years as a kindergarten teacher and one year in a seventh-grade classroom in challenging areas of the city.

While Skibbie was teaching, a friend of hers worked as a nanny for a country singer/songwriter and her husband. On a few occasions when she needed a sub, the friend asked Skibbie to step in. When her friend left the job, the family came to Skibbie, asking if she wanted to serve as nanny to their then 2-year-old son.

“To me, it was an adventure to work with the family,” Skibbie said. “They were planning on traveling, which sounded fun, plus they were great people. I also had taken on some debt and saw this job as a great way to pay it off.”

Originally, Skibbie planned to work only a year before returning to the classroom, but one year turned into nearly two.

“I loved the little boy I cared for,” she said. “I did a little preschool program with him. We also went to parks, museums and different classes. The parents were very intentional on how they parented and wanted my feedback. They were a great family and I miss them.”

A musician’s life is busy with writing and performing music, going on tours, promoting the work via print interviews and TV appearances, meeting with other singers and songwriters and attending different events. Skibbie was on the sidelines for some of the excitement, but prefers not to talk about it much because of her loyalty to her former employer. She went along on some tour dates with the family while staying back in Los Angeles with the singer's son for others. 

Being with the family was amazing and I had experiences that I never would have had otherwise,” Skibbie said.

“One of my best memories was traveling with him to meet his parents in New York (who were in Europe finishing up a tour). Before they arrived, we had time to explore the city together,” Skibbie said. “It was a wonderful experience.”

When the parents traveled, Skibbie cared for the boy 24/7.

While the family resided in Los Angeles, Skibbie did not live in, and typically worked 9 a.m. to 6 p.m., putting in one later night each week. Last fall, the family moved to Nashville so the singer could work on her next album.

“When you are a nanny, you become part of the family,” Skibbie said. “While that’s great, it’s hard when you need to have ‘business’ conversations.”

Last Christmas, she told the family she was ready to return to the classroom and began looking for a teaching position for this fall while continuing to nanny.

“I worked really hard to get my teaching credentials, but the nanny experience allowed me to sit back and reflect on the teacher I wanted to be. They supported my move,” she said. “I started applying for different programs and schools where I felt I could make a difference.”

That led her to the Success Academies. She had a friend who taught at one of their 44 schools and heard plenty of positive things from her. Skibbie also longed to live in New York and experience everything the city has to offer.

In her first few weeks of work, Skibbie will mentor under another teacher and float among various K to 4 classrooms before being assigned a class of her own.

“Even though these schools are in mostly low-income neighborhoods, they are high-performing,” she said. “They have a great philosophy and are very intentional about what they do. I’m very excited and eager to see how it goes.”

Aug. 2,