In our conversation with Amy O'Leary, she discusses what led her to become interested in early education, her philosophy around respecting children and integrating them into society, the importance of mentorship and more.read more
Tell us about your background. Were you born here?
I have two older brothers; there are three of us total. And they were born in the Boston area and grew up in the South End. When I was born, my father and mother moved us to Quincy because we needed more space. That’s when my mother transitioned from being a teacher at the day care to an assistant director. She felt that having three boys meant that she needed more income. The job opportunity was available and she knew it was the right thing to do. Both my brothers and myself have godparents who were teachers with my mother. At the time, she would invite all of the teachers and their kids to her birthday parties. And my mom was notorious for hosting all of these events, whether it was a summer barbecue or a birthday party. So, it was very family-oriented. Everyone would come together regardless of your background or your skin color. It was very powerful for us.
She raised her three boys to treat every lady as you would treat her. And she made it so that we respected all of our teachers as though they were our mom. Not to mention that the news would have gotten back to our mom if we didn’t do that! But even after we left day care, she would say, “Why don’t you go around the classrooms and see if they need any help? And she would point out classrooms and say, “Ms. Wong had a shoulder injury last week, so how if you lend her a hand and see if she needs help with the water?” It could be something as simple as that, but we carried that on into our adulthood, where we’re always just offering a hand. That’s where the term, “Well, if we can, we will,” came in. If something was in front of us, it was there for a reason.
Our dad used to give us a metaphor: if you’re walking down the middle of the road and you trip over a stone, it’s your obligation to move that stone so that no one behind you trips over it. My parents always felt that these lessons would travel with us down the road, and they obviously did.
My mother worked in the field of child care for 37 years and families came to her to ask, “Where should I place my child? What kind of future should I give them?” And she would always suggest Ellis and she would pinpoint every reason why Ellis would be good for them.
After school, my parents would help me with my homework. They would explain the instructions because at the time I couldn’t read. This is why I’m such a big promoter of reading. I was a late bloomer. I didn’t really grasp reading until 4th or 5th grade. It was something that a teacher taught me. She said, “You’re very wise when it comes to math. You can do the numbers, but if you can’t read, you can’t succeed in this world. It’s important that you pick this up. So, every book that comes your way, you’re going to gain that knowledge.” And this was part of a generational message: knowledge is power.
So that’s something I like to bring into the classroom, especially with the kids, who love superpowers. I tell them, “You can have superpowers!” They’re thinking Iron Man, or Frozen, or Superman… And then I point to where their brain is and I say, “Friends. That is the most powerful thing you have. You need to unleash it, understand it and, if you can even grow it more that is the most important part of your body and we need to protect it.”
I learned this from everyone who was there for me. Everyone I grew up around. They also taught me that all of us have to grow. Students at Ellis have to move on when they age out at the age of 13. And when students are upset about leaving, I tell them, “There is so much beauty out there that you don’t even realize yet. But you’ll get it and you’ll see it and you’ll appreciate it.”
When you walk into Ellis, you feel like you’re entering your second home. You don’t feel like you’re even at work. One teacher at Ellis taught me the idea of creating a blueprint for someone’s success. Not just thinking about the next 10 years, but breaking that down for a young individual and telling them that they are going to create a track, a blueprint, and I want you to stay the course. If you really have a dream and you really have a passion, I’m here to tell you that you can do it. I’m here to say “yes, you can.” I want you to keep that motivation in you.
A teacher at Ellis told me that only a small percentage of the children at Ellis have fathers. So, she said, “Cliff, you’re taking on a bigger role than you think. And I need you to understand that.” I take that seriously.
So, that really cut deep in a good way. It helped me when talking with students who didn’t have their dad around or only saw their dad once a month. When they voice that to me, share that with me, it really shows me what I mean to them. I know I have to work extra hard for those students.
For instance, one student got robbed one weekend. And he seemed broken by it. I knew that a normal routine response wouldn’t be enough. I knew I had to give him something else. I knew I had to give him some perspective. What he wanted was to get out of Madison Park. [Madison Park is a housing development in Roxbury.] He wanted to take care of his mom so that she wouldn’t have that fear. And I said, “Hey, the power is totally yours and you’re capable of that. So, let’s talk about the blueprint: How are you going to get this for you and your mom?”
So, to see the fear that he had about the fact that anyone could come into their apartment and rob them, and then counter that with the power of his blueprint really helped. He said, “I’m going to move out with my mom and I’m going to get us to a more secure and protected area.” That was a nice feeling.
I asked him to step out on the balcony and just have a talk. We stepped outside, and I said, “I want you to pick something and name it for me.” So, he said, “I see a mailbox.” And I said, “Let’s expand upon that. I’m going to do a 360 slowly and I’m going to name as many things as I see, from a cloud to a playground to a swing.” After I did it, he went. And he probably named 30 things. And then I told him, “When you’re sad, when you’re scared, when you’re angry even, when it seems like you can only see one thing, just like you only saw the mailbox, know that it’s tough to live your life focused on that one thing. But if you’re calm, if you’re happy, if you feel loved, if you feel at peace and are grateful for everything life has, then you have unlimited possibilities.”
And later on, his whole attitude changed. He became more helpful with every student he knew he could help. And then eventually, he was happy again. He realized the power he had. The blueprint changed for him.
One of our students experienced the Boston Marathon bombing. He was actually in the middle of both bombings with his father. I spoke to that student and helped him to realize that he was in a safe place; that this was his second home. I said, “You’re with all of your friends. You and your dad are both fine. I’m so sorry you experienced that. I’m so sorry that we all experienced that. But it had nothing to do with you.” And then I added all of the positive things in his life: his mom and dad, the fact that he was safe and he had all of his friends. And half an hour later, I could see his composure return. He was much calmer and he was back to himself.”
I say to the students, “The first month of school, I give you thumbs up for being smart. The following month, I give you two thumbs up and I tell you that you are super smart.” They try to earn that extra thumbs up. And by the third month, I teach them the word “intelligence.” I say, “You guys are intelligent and that means you’re super smart. Then toward the end of the year, I tell them they are “super smart” and I ask them what that means and they say “intelligence.” The curriculum has to be about more than getting B’s and C’s. There is another level higher up. I feel like we’re reaching for the stars. I mean, you can reach for the moon, but if you don’t make it, you always have the stars. So, I say to the students, “Wow. You are learning way more than I ever did at your age,” and they love it.
Do you think about doing what Amy (O’Leary) did and eventually leave teaching to work as an advocate for early education?
I don’t just plan for next week or next month. Some of the most successful people in this world plan for the next five to 10 years. And as you plan that out, you’re constantly checking things off and getting things done. That’s what the blueprint to success is. Along with that, at the age of 10, my godfather taught me something about helping. We were going on a trip to the Philippines, and he said, “The moment I became your godfather, I’ve always watched over you. And the thing I’ve noticed is that you’re always willing to help. But before we go to the Philippines, I need you to understand that you shouldn’t help everyone who comes to you. Although people are going to want your help, you need to understand where they’re coming from. Everyone deserves a helpful hand, but you need to understand how genuine they are and what your help is going to do for them.”
So, when I think about the future and coming years—not knowing how many days and years I have left—I want to help as many people as possible, but knowing that the help I’m giving people is actually for their good. I need to know that it’s paying it forward and that if I help one person, it’s going to help others.
As far as growth, I love teaching, and it’s nice being able to help my students (usually there are 20, but now there are just seven), but as I get older, I want to help more. I’ve been in meetings with Boston Public Schools and a foundation from Ohio and helped to convince them that by donating to the BPS, they can help online learning. I told them, “You’re not just helping one life; you’re creating a ripple effect or a domino effect. And it’s helping many other lives that you won’t ever even see. But through your help, you’re creating so many opportunities for other people."
When we’re no longer alive and no longer here, our lives will still be helping people and that’s the most powerful thing I can do. And so working with the BPS and other teachers feels very inspiring to me, because I know it will help so many people. It pushed me further.
We’re not aiming for the A’s, B’s and C’s anymore. We need to go past that and we need to aim for the sky. If we reach for a higher letter than the letter A, our students are going to be on a higher trajectory than they could ever have imagined. So, when I was working with other teachers and they were listening to me, it inspired me to go farther.
When you step back and think about Boston, especially having known it all your life, what do you think are some of the biggest challenges we’re facing as a city?
I love teaching and helping my students, but as I get older, I want to help the whole city. I have the heart of Boston within me. I think the main thing is that everyone wants to know that they’re cared for. Everyone wants to know that they have that safety net. And, when there isn’t a safety net, that’s where chaos is created. To show more of that care, to show more than, “Hey, we’re here for you. We’ve been thinking about you. Are you alright? Is there anything we can do? Do you need any supplies? Do you need extra resources? Do you need food on the table?”
I don’t think it should just stop at the safety net. I also feel that there should be additional levels of help. It might be putting food on the table. It might be a computer, so a child has something to learn from. There are multiple levels of help we can offer.
In the area of early education, what would you like to see happen?
I learned this at the Foundation when I was there for a forum with Brian Gold. He said that there are fewer and fewer students who are trying to become teachers. The number of students in colleges and universities pursuing teaching is declining. If this continues, we’re not going to have enough teachers. That’s daunting, and it’s something we need to fix. A lot of teachers are concerned about going back to school in the fall and they’re worried. Some are living paycheck to paycheck and have to work to support themselves and their families. A lot of teachers are single mothers. Some have the extra support. I know one teacher who left teaching because her husband was able to pay their mortgage and she decided she wanted to take care of her daughter. She didn’t want to get sick or get her daughter sick. She’s entitled to feel that way. It’s totally understandable.
I think we need to have more resources for the teachers we have now, but we also have to find a way to encourage more people to become teachers. I know a lot of students who stay away from teaching. My mom told me that you’re going to have a lot of loans when you go to graduate school, and when you become a teacher, you get paid very little. If we can’t pay teachers more money, how about giving teachers free tuition? Why wouldn’t you want more teachers to teach our future generations? Why not have more incentives? They commit their lives to human beings.
We need to grow more teachers. Maybe it’s student loan forgiveness. Maybe it’s giving back to your community after you’ve served three to five years, and then your school loan is forgiven. We need a blueprint for growing more teachers.