Heather Anichini (Chicago ‘99) never set out to lead one of Chicago’s most influential education funds. She just wanted to stay close to the communities that raised her, the families that trusted her, and the city that taught her what leadership really means.

After serving on Teach For America’s national staff, where she expanded leadership programs for educators nationwide, she came home in 2013 to reimagine The Chicago Public Education Fund. “The Fund was started as a venture philanthropy,” she says. “We raise and spend dollars in cycles, partnering with Chicago Public Schools and others to identify where an organization close to the district can be useful.”

When Heather Anichini became CEO, she didn’t reinvent the mission; she refined it. “Our board isn’t made up of many educators,” she explains, “but they know leadership makes an enormous difference.” She helped shift the Fund’s focus from broad-based philanthropy to a deeper investment in leadership development. “When we started, we had 13 principals, half Teach For America alumni,” she says. “Today, we serve more than 250 principals, 150 aspiring leaders, and their teams. We work with local councils and network chiefs to make sure Chicago is the greatest city in which you lead a public school.”

Heather’s story from there is less about titles and timelines and more lessons rooted in trust—trust in people, in possibility, and in what education can unlock.

From Nuns to Neighborhood Classrooms

Heather’s family believed in education so much, they reshaped it in their own creative way, long before it was trendy to disrupt.

“Imagine being thirty when the printing press was born,” she says. “All books had been handwritten, and you only had access if you were rich or a priest. That’s why all the women in my family became nuns so they could read.”

That legacy taught her education should be shared, not hoarded. And as a young professional on Chicago’s West Side still figuring out what “real change” looked like, that conviction led her to a job working in college-access programming. Here, she saw how limited opportunity could shape a student’s sense of what was possible. “Most of the students and families I worked with, like my own, hadn’t had access to college as a way of thinking about what came next,” she says. It was during that time Heather knew she wanted to make more of an impact, but she didn’t know how. A local principal presented her with a life-changing option, and challenge. “She just said one day, ‘If you really want to do this work, you have to teach.’”

At first, the idea felt impossible. “I’d gone to Marquette and was making less money than my last semester of college probably cost,” she laughs. “The thought of figuring out how to teach without a degree was overwhelming.” Still, Heather found herself drawn to the challenge.

Shaping Education–It’s a Family Thing

Teach For America had just arrived in Chicago, and something about it clicked. “The idea was about making sure students had the same quality education I’d benefited from every day,” she says. “So I applied.”

Her first teaching team became her foundation. “Two veteran teachers on our middle-school team were the best I’ve ever seen,” she says. “They worked hard with the students we had. I felt lucky to have stumbled on TFA and to have been supported by the network ever since.”

Her biggest lessons, though, came from watching her mother. “My mom graduated from college the semester after me,” Heather says. “She was teaching high-school math with students who sometimes had one-on-one aides.” Heather completed her observation hours for Teach For America in that classroom and remembers being struck by what she saw. “If you didn’t know what I knew walking in, you wouldn’t know which students needed extra support,” she says. “Watching my mom do it so well made me believe it was possible,” she says.

And when Heather needed extra hands in her own classroom, she turned to family. “I have a million cousins,” she laughs. “There were days you’d walk in and see twelve of them helping with floor-sized geography maps. Who can understand geography from an 8×10 map?”

It’s what she still jokingly calls “personalized learning before computers”—a core memory that reminds her how creativity, family, and faith in community can make anything work.

Listening First, Leading Second

Two decades later, Heather still leads with that same belief. Her role as president and CEO might have changed her title, but not her approach. She still picks up Saturday calls. She still joins the group texts. She still listens. That commitment to listening has carried her through nine CEOs, three mayors, and countless shifts in education. “I try to stay connected to the next generation of leaders,” she says. “We talk about what they’re seeing, what they’re worried about, and where I can make connections between those challenges and the resources to move things in real life.”

Even with experience and authority, Heather keeps her humility. “I’m almost fifty. A white lady,” she says. “I’m not the best positioned to know what the students we serve want or need. I don’t even know what my sixteen-year-old wants, and I live with him. But there are people in my network who do. So I listen.”

For Heather, listening exemplifies leadership. “As a leader, you have to make people feel safe.” she says. “You hold space for people without scaring them too much. You help them think, ‘What’s the next best thing we can do?’ But make sure nobody thinks it’s the solution. Because there’s always another next best thing.”

Learning to Trust the Detours

Like several other TFA alum, her leadership philosophy is what got her into the Pahara Institute Fellowship, a highly selective, values-based leadership development program designed for senior leaders working to advance education and excellence in the United States. Heather had spent decades building leaders across Chicago. Still, she didn’t see getting into the fellowship as inevitable. “My last year teaching was in the early 2000s, and I’m doing Pahara now, twenty years later. I’m a non-traditional everything.”

She admired Pahara from afar, watching cohorts of values-driven leaders wrestle with identity and impact. “I needed to grow so that when I got the call, I’d be centered for the work.” When that call came, Chicago was in flux. A new board, new mayor, new challenges. “Being part of Pahara now is a good lesson in what I learned in the classroom,” she says. “Opportunity comes when it’s meant to, and your job is to receive it and use it in service to the work.”

Her first session centered on identity. “To be in a room with people across every line of difference and reflect on how hard the work is. That was powerful,” she says. “The work is heartbreaking. It can be soul-crushing if you let it. But if you’re not failing, you’re not doing the hard work.”

Keep Going Anyway

When Heather thinks back to her first classroom, she smiles. “I’d tell her to do it all again,” she says. “I learned more in the five years around when I was teaching than in the ten after. I failed at so many things. But I felt responsible, and I kept trying. I built relationships. I invested. And I wouldn’t trade any of it.”

The willingness to keep showing up, keep listening, and keep learning has shaped everything since.

Heather Anichini’s story is one of quiet conviction. A life that proves leadership isn’t about speed or spotlight. It’s about depth, stillness, and faith in what people can become when someone truly believes in them.