From Mayflower Hill to the Mississippi Delta

If you asked Joseph Whitfield ’15 after his four-year tenure as Colby’s Class of 2015 president, he would have told you he wanted nothing to do with politics. And yet, today, Whitfield finds himself as mayor of his hometown, Helena-West Helena, Ark., at the forefront of local politics, where his Colby friends expected him to be.

Whitfield did not come into this role through a traditional campaign but through a call to service from the governor of Arkansas, Sarah Huckabee Sanders. After two months of discussions about the office’s responsibilities, the commitment was confirmed by phone. “The governor called me on a Monday, I said yes on Tuesday, and it was announced on Wednesday,” he said. “The stars aligned.”

He started his responsibilities in the historic Mississippi River city in October 2025.

Before entering municipal government, Whitfield spent nearly a decade in education as a teacher and high school assistant principal. All the while, he absorbed the advice his mom poured into him throughout his childhood. It’s always important to “give back to the people who gave to you,” she told him.

Whitfield, who majored in English and literature, brings his mother’s advice, his experiences at Colby, and lessons from his time in education to his new role as mayor and community leader.

Whitfield began his teaching career in a Helena middle school through Teach For America’s Knowledge Is Power Program (KIPP).

The program was a “godsend” for his community, he said, as there was a teacher shortage and difficulties recruiting teachers to the small community. After witnessing Teach for America’s impact on building a stronger community by addressing the teacher shortage, Whitfield was motivated to complete his service in his hometown.

 ”Some of those teachers I had back in middle school and high school still live in this area,” he said. “They have their kids here. They have their families here. They opened businesses here. They bought homes here.”

After completing a two-year commitment to Teach for America, Whitfield built a career in urban education in New York, starting as an English and social studies teacher at Harlem Children’s Zone and later teaching English at New Heights Academy Charter School through the pandemic. He leaned into his passion for education and service as the classrooms around him shifted and everyone reinvented daily life.

Whitfield faced a pivotal moment at his end-of-year review. He spoke candidly about the “façade of education,” arguing that schools should focus on student outcomes rather than optics alone. He wasn’t invited back, but the experience solidified his belief that students deserved more than the standard curriculum.

Whitfield moved into education consulting, shifting his work beyond the classroom. Building on their firsthand experience with the rising literacy crisis, Whitfield and his wife, Shadey, founded Lit for Life during their time in New York City. The small, grassroots tutoring-and-writing company helps students learn to read and write at any educational level.

Even as his career has expanded to municipal government, Lit for Life remains a passion project and a testament to his belief that literacy is essential to a functioning community. “Education is the heartbeat of your community,” Whitfield said. As mayor and former chamber director, he sees firsthand that competency is essential to developing and maintaining a community.

He and Shadey left the bustling streets of New York City after seven years for a slower, rural landscape in his hometown of Helena, where he transitioned from the classroom to local community organization Delta Magic and later the Phillips County Chamber of Commerce. Working for those organizations, he quickly realized the skills needed in the classroom were also essential for building the community.

He views his time in the classroom as the building blocks of his career.

“Management, planning, and communication are some of the skills you build in that setting,” he said. “Every facet of character development I’ve gotten through education is being used in my role right now.”

His guiding principle is listening to his community. “We’re having town halls that are bringing the public into municipal government for the first time in a long time,” he said. “We recognize that people want to be involved.”

When Whitfield arrived at Colby, the transition from Helena to Waterville felt less like a culture shock and more like a mirror image. “Helena is very much like Waterville,” he noted. “Geographically, I grew up in a small town just like Waterville, where you know everybody, and there are a couple of things to do in each corner.”

His return to Helena was solidified when he was approached by a member of the Delta Magic board about a revitalization project to convert an abandoned downtown building into a dormitory for a local community college. To his surprise, Colby was used as the case study for a blueprint about a successful downtown investment by a local college.

“It was really cool coming home because it was a full-circle moment,” Whitfield said. “It was confirmation to say I was in the right place at the right time to bring back what worked at Colby and in Waterville and replicate that here.”