Justin Pitts (Chicago, ‘13) is the Assistant Head of School at Beacon Academy in Chicago. A seasoned educator, he’s spent years leading classrooms, supporting principals, working with system leaders, designing curriculum, and developing processes for teacher recruitment and evaluation. As a teacher coach, he’s impacted the careers of hundreds of educators. His passion for education runs deep.

But it almost didn’t turn out this way.

An Unexpected Start

As an undergrad at Auburn University, Justin spent the summer of his senior year weighing his next move. While he enjoyed studying finance, he couldn’t picture a future in the corporate world. What he did know was that he loved working with kids—a discovery he made while volunteering at the Boys and Girls Club.

“I had that experience in the back of my mind when a TFA recruiter approached me,” he recalls. “I was president of the student senate at Auburn and an orientation leader for freshmen. It was the classic TFA story: you're a campus leader, so you’d make a great teacher. Let’s talk.”

Initially, Justin didn’t see himself in education. But after plenty of encouragement, he applied and accepted an offer to join Teach For America. He spent his two-year commitment teaching fourth grade at a Chicago public school.

Though his time in the classroom was deeply rewarding, navigating the politics and bureaucracy of the school system proved unnecessarily difficult. Eventually, Justin decided to step away from teaching.

“At that point, I’d concluded teaching wasn’t going to be my forever,” he explains. “I decided to use my degree and became a financial analyst. And I absolutely hated it. It was the worst decision I could’ve made.”

Unfulfilled in finance and unsure of his next steps, it was his husband, Jonathan Chaparro (Chicago, ‘08), who suggested he return to the classroom. Justin initially dismissed the idea but agreed to stay involved with TFA. The couple signed on as regional outreach captains for the 25th Anniversary Summit.

“It was a great setup. You encouraged your TFA network to register for the Summit. If 20 people signed up, your flight and ticket were covered. I started reaching out to friends who had moved out of Chicago and said, ‘Hey, you should go. We’ll all hang out in D.C.—it’ll be fun.’ I got 20 people to register and went for free. Little did I know that trip was going to change everything.”

A Turning Point

For Justin, attending the 25th Anniversary Summit wasn’t just an event—it was a catalyst. He arrived in D.C. with no expectations. He left with a completely renewed sense of purpose.

While the breakout sessions and speaker panels were meaningful, it was the opening ceremony that overwhelmed him with emotion and clarity.

“It was miraculous. I still get emotional talking about it. It was the smallest moment of the entire event, but the most powerful. For a couple of minutes during the welcoming ceremony, all the lights went out, and our RFID bracelets lit up. That was it. And yet it was everything. I felt this overwhelming sense of connection and shared mission. I just knew I couldn’t imagine life without this community.”

Justin flew back to Chicago on Sunday. By Monday, he was in his boss’s office giving notice.

He gave himself two weeks to return to education—and he did. He accepted a position teaching in the Noble Network of Charter Schools, which serves middle and high school students across Chicago.

Coming Full Circle

That marked the beginning of a new chapter. Once a finance major and analyst, Justin had become a purpose-driven educator.

While at Noble, he built strong relationships with students, families, and the broader community—work that didn’t go unnoticed. As the recipient of the Frances & Elliot Lehman Alumni of the Year Award, he was recognized by Teach For America for his outstanding impact on students in Greater Chicago-Northwest Indiana.

But Justin’s passion extended beyond the classroom. He remained closely tied to TFA, working for the organization for six years, including time at training sites and as the regional director of virtual learning for TFA Idaho. He earned his graduate degree from Indiana University School of Public and Environmental Affairs (SPEA), expanding his ability to serve students through curriculum and systems design.

Now, as Assistant Head of School at Beacon Academy, Justin continues to lead with impact and is already looking ahead to the 35th Anniversary Summit in Las Vegas.

“I don’t know what will happen, but I think I’m going to have a moment. I love the work I do now, but if the 25th taught me anything, it’s that you never know what small moment will spark what’s next.”

Justin is excited to see where the 35th takes him and what it might inspire in others.

“No matter what, I know I’m going to feel something at the 35th. Because TFA is about all these small little things adding up to something big. The 25th deepened my connection to the mission and helped me reimagine my career. Who knows what the 35th will spark?”

His Advice to Fellow TFA Alumni

“I feel incredibly lucky that I randomly applied to Teach For America. Staying connected to the organization as an alum isn’t always easy—life gets busy, especially if you’re working outside of education.”

But Justin understands there’s real power in showing up. “Going to the Anniversary Summit isn’t just a reminder of a shared purpose,” he explains. “It’s about reconnecting with the small moments—and the people—that brought you to where you are now. It’s emotional, yes. But it’s also deeply powerful. And it can be life changing.”