Amy O'Leary standing outside, a brick sidewalk trailing behind her along with green trees. She's wearing a black dress and a stone necklace, smiling. She has short brown hair and bangs. It's a sunny day.
Amy O'Leary
Read the full 2020 Annual Report
Families and Children First

Amy O'Leary

Director, Early Education for All 
Strategies for Children


Tell us about how you found your way to Boston and the work you’re doing now. 

I graduated from Skidmore and everyone I graduated with was deciding whether to move to Boston, D.C. or New York. I had a B.A. in Psychology and Education. About 20 of us moved to Boston and all found jobs. It was in the ‘90s, so it was a tough economic time. But I asked the alumni office for a list of alumni who worked in Boston with children. And that’s how I met Margaret Blood. [Margaret Blood founded Strategies for Children.] I knew I wanted to teach young children. But I wasn’t certified to teach, so I didn’t go the traditional teachers’ route.  

Margaret connected me to other people in the field. I got my job at Ellis through the want ads as a pre-school teacher. From the minute I walked into Ellis, you could just feel the culture of supporting children and families. They had programs starting at birth and going up through school age, so for many of the kids, Ellis was their home base. So, as a teacher, to be able to connect with your kids as they go on and went into kindergarten was such a gift. And you really became integrated into the families. I say that I got a master’s degree in life at Ellis, because the parents and children taught me so much as a young teacher and then as a young director at the age of 26. So, I was an administrator, but I also covered the classrooms.  

In Boston, in the mid-‘90s, there was an infrastructure to support young directors like me so we could learn from seasoned directors who had been rooted in the community for a long time. Unfortunately that infrastructure doesn’t exist anymore. Back then there was funding available. We had the Boston Childcare Alliance and the Inner-city Network of Directors. So, I had a ton of support within the city of Boston. As the recession hit, the funding for much of that went away. We’re just beginning to think about how to rebuild that. One of my hopes for Boston is that we can think about reconfiguring that. 

I started at Suffolk when I was still at Ellis to get my MPA (Masters in Public Administration). I appreciated the diversity: There were 30-year veterans who had been working at the state house or at agencies along with local government folks and people who were interested in policy. I went part time and it took me five years.   

I worked with two revolutionary mentors: Leo Delaney and Margaret Blood. Leo really understood the value of being part of the community and encouraged staff to be part of the community in whatever way was possible. That infrastructure meant that there were people whose job it was to support young children in Boston. So, that was a significant part of my development. Because we learned together, we had opportunities to solve problems together. So, as a director, I had to figure out how to fully enroll children in my program as well as pay attention to the funding streams. That’s really when I became interested in policy and advocacy.    

I was at Ellis for nine years, three years as a teacher and six as a director. I had kept in contact with Margaret Blood, and as she created Strategies for Children, we connected. Ultimately, she hired me as an early childhood field director. Margaret continues to be one of my biggest mentors. She’s taught me so many things about policy development and networking and connecting and being an advocate… She also taught me what it takes to really build a movement.  

So, I’ve been with Strategies for Children for 18 years and have played different roles and learned different skills. It has been an amazing experience. Margaret always wanted an early educator to lead the campaign. She’s always been a child advocate, but not necessarily an educator.  

What led you to become interested in early education originally? 

I think, like so many women my age, I grew up babysitting. But my mom was a huge influence. She believed that children were competent and capable. A lot of her work as a volunteer was about supporting children and families. In our family, education was important. 

What is the status of your campaign now? What are you struggling with? 

I think the frame that the Boston Foundation is taking for this annual report is so significant. I think if we had had this conversation in February, I would have had very different answers. I think the challenges facing Boston are enhanced by our history, by the deep community roots that people have, the commitment to change and thinking about what could be. What would it really look like if we were a city that put young children and families first? And how that would be integrated into everything? I don’t think it’s just the role of government to do it; everybody has a role to play. But what would that really look like? What would our policies look like? What would our physical spaces look like? What would it feel like to be in a community that really had that as an opportunity? 

I had the opportunity to visit Reggio Emilia in Italy, which respects children. There is artwork all over the city, made by children. Their programs are very visible. In fact, one of their tag lines is “making children visible.” Now, you can’t pick up the model and just put it down anywhere. But we can take the principle of questioning how we integrate children into society and how we can have respect for children.  

One of the things that has been so amazing about reconnecting with Clifford Kwong, is that he has a very similar philosophy to mine; of respecting children and understanding what the role of a teacher is. He has a strong commitment to not waver on that. He is very humble in the work that he does. He has developed a very strong sense of self and purpose. He considers every decision he makes in terms of respecting children. If children have caring adults in their life and are given opportunities to practice and to learn new skills, those are all you need in your life.  

Whenever I’m around children and I ask them a question, sometimes parents will answer for them. Especially young children. It’s a bit of a shift to ask the child: What do you think about that? 

Why do you think that this is a particularly ripe time for change? 

We talk a lot about the fact that, before COVID, the early education system was already broken. Teachers were undervalued and overlooked. Programs were one payment away from having to shut their doors. The inequities of the system have just been exacerbated, as far as who gets what. And I also think that, as far as waiting for someone to figure it out (we’re looking for leaders), I believe that we can solve our own problems. And I think what has happened in the last few months is that early education and schools have come together in this crisis to say, “We have to figure out a better sustainable model. We may have to shift a little bit. We may have to be more accepting of proposals that we wouldn’t have entertained before. But we can’t keep going at this alone. We’re going to have to work together.  

"I think the energy of young people and the conversations that have been started would have been taboo to discuss in certain settings. To be denied a seat at the table, whether it’s police brutality or racial injustice, you can’t just pretend that, as a leader, it doesn’t fit into your work."  

Do you think it feels like we’re almost starting over in a way? 

We are. I think the energy of young people and the conversations that have been started would have been taboo to discuss in certain settings. To be denied a seat at the table, whether it’s police brutality or racial injustice, you can’t just pretend that, as a leader, it doesn’t fit into your work.  

I do think that the forthrightness and the acknowledgment of young people is great—and their willingness to stand up and take risks and reimagine what a future could be in this more inclusive environment, while also helping people see what part they’re playing in. And I think that when you think about the city of Boston and the legacy of such strong leadership, it can be easier to let someone else figure it out. I think that for the Mayor and the School Committee and the City Councilors, you have seen younger people running for office. That includes people who didn’t take the typical route to become an elected official. People are coming from all different kinds of experiences.  

There is an opportunity in this disruption, to be shocked out of the way we’ve been doing things. I recently was in a group that asked for one word to describe early ed right now. My response was “seeing!” I think people are seeing where early education stands. The one thing that sits in the middle of everything is the question: “How are we supporting children?” Some of the decisions that we’re going to have to make collectively are going to be very critical. We have to think on the national level, the statewide level and the local level. How can we think intentionally about where all the resources are that we need for children and families? What would it take for everyone to really work in concert with each other? Who’s going to be the leader of that? 

My youngest brother is the director of an opera theater in Washington and I think a lot about his role as the conductor or a facilitator, which is another very important part of leadership. To be a good conductor, you have to have some knowledge about what everyone’s doing. You have to be aware of the big picture. Just having that one person who might not be the lead in the play, but is a structural leader. I think in any community, you have structural leaders to look to. But we also have these conductors throughout the city of Boston. How do we give those conductors the support and opportunity and time and space to try some things out? We may need to reimagine what could be.  

Amy O'Leary and Cliff Kwong standing on a brick sidewalk in Beacon Hill. Trailing behind them are brick buildings on the left, the brick sidewalk, and a paved road to the right. Green trees in the distance and an American flag hanging at the above them. It's a sunny day.
Amy O'Leary and Cliff Kwong
Read the full 2020 Annual Report

One of the biggest questions we get from elected officials is, “What do you want me to do?” And I think sometimes we don’t have good answers for that. Or we have unreasonable answers, such as, “We need $500 million.” I think now we have an opportunity to think about who we are as a community. What do we value? We know that there are these wise ambassadors in all of these different places that can be very hard to find and to see. And I think your question: Where are the next leaders? It could be someone running for office. 

But the reason that I chose Cliff was that it was really important to me to pick someone in a classroom. Who gets a voice? Who decides? And who’s not even in the conversation? I felt like a Bostonian, probably for the first time, when Cliff connected with me after so many years. I realize that I have taught in Boston and here he is continuing the work in the same place that I did the work. I think that’s where our history is a strength. As a teacher, all you wonder is, “How did my kids do? Did they find happiness? Where are they in their lives?”  

As we think about who’s going to be on boards of organizations and the important work that we’re doing and we can have more intentionality about the work and not duplicating and really allowing the space for new thinking… The opportunities in a place like Boston are just incredible. When you think about the leadership capacity that we could build with all of the institutions, both public and private. To have the State House here… To have all of the rich community resources… we need a conductor to bring it all together. You need a narrator. Who’s keeping the history of Boston?  

We’ve talking about some of your big ideas. Do you have others? 

I think another big idea is this concept of mentorship. Everyone in Boston should be a mentee and a mentor. We should be thinking about how we are helping people and crossing artificial lines… Sometimes we get in our own little bubbles. How can we be thinking more about what we can learn from other people and what we can add. We can be thought partners to people as they grow into adults. I was so fortunate to find Margaret, who was willing to put so much time and energy, to take me everywhere—to the state house and to funder meetings. You need someone to teach you the ropes and give you the opportunity for reflection and to see yourself in a leadership position. The question is: Who belongs at the table? And making sure that we are thoughtful about that as leaders. How do you transfer your skills as a leader? Sometimes we set up barriers.  

I believe in learning by doing. And I’ve been able to experience a lot of firsts in Boston… This idea about being rooted in history, but thinking differently about the future is such a big opportunity.