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Penny Bailer


Whole School Whole Child Dropout Prevention

1 Ford Place
Ste. 1F
Detroit, Michigan 48202
City Year Detroit’s Executive Director, Penny Bailer, is a 37-year resident of Detroit with a firm grasp on the vital need for education improvement in Detroit. With a zest that is rare and unmistakable, Bailer oversees the many mentoring, educational, and enrichment programs that City Year offers to the city’s underserved youth.
Michigan Nightlight: What does being a leader mean to you?
City Year Detroit’s Executive Director Penny Bailer: Being a leader gives you the opportunity to motivate others to join in your crusade, whatever it is: mental health or any number of social issues.
My number one issue is education, and if you track ACT and SAT scores, you’ll find that, typically, the lower the household income, the lower the students score. There are always exceptions to this, but, generally speaking, poverty almost always determines who scores the lowest on standardized tests. Middle and higher income students usually score better.
I was lucky enough to grow up in a middle class household with lots of support, and I am determined, as a leader, to do my part to help those who are not as fortunate as I was. As U.S. Secretary of Education Arne Duncan says, “Education is the
If education were the top priority, we would not have to spend billions on prison budgets.
solution to poverty.
What is your dream for kids?
My dream is that every kid in the nation can have a great education from kindergarten all the way through college. You cannot get a job today without a high school diploma, and you need to have at least a two-year degree to get a good one.
Partly because of advancing technology, society has changed over the past 20 to 30 years. Regardless of whether you want to be a musician, an artist, a doctor, a lawyer, a carpenter, a business person or a homemaker, you need a good education in order to be successful.
What is one concrete thing that could be done to improve the environment for social sector work in Michigan?
To make education the top priority, especially for ages zero to 21. If education were the top priority, we would not have to spend billions on prison budgets. Those expenses are currently projected based on fourth-grade reading scores in Michigan. For example, if we spent what we are spending now on crime and incarceration on education, we would have a more positive population of productive citizens – citizens who pay taxes, who are self-sufficient, and who can raise families themselves without public assistance.
I’d much rather spend $30,000 a year on education than on prisons, especially for kids who live in poverty and who often need a tremendous amount of extra support. We will pay for this one way or another. We will pay now or we will pay later. That’s how it works. I’d rather pay now.
How do you know you’re making progress?
When you can see the measurable outcomes of your work, and they show positive improvement, you know that you are making progress.
We mentor and tutor kids who are off-track in school in order to get them back on track for graduation, and we track their progress as they go along. We start with the baseline data, where each student is when they start school, and we measure this weekly and monthly so that we can adjust the program based on the needs of each particular student. Every individual doesn’t respond to the same intervention, so we plan ahead to adjust things according to their particular needs.
We use the Johns Hopkins University research method called “Early Warning Indicators” that measure danger signs of future
...studies show that, as early as the sixth grade, a child who is off-track in even one of the
dropouts. The data has to come from the schools, because studies show that, as early as the sixth grade, a child who is off-track in even one of the “ABCs” – attendance, behavior and course work [in science and English], is in already danger of dropping out of high school.
Nationally, only 75 percent of those kids will graduate from high school without early intervention, but with it, we can bring that number up to 80 percent. We are addressing the education of our children, and that is the number one issue in Detroit. This is not magic. It is hard. But it does work.
What are you most proud of?
Let me tell you one of the most poignant dropout intervention stories I have ever heard: one that I’m very, very proud of.
I know a principal in our area who was recruiting eighth-grade graduates to come to her new, nearby high school and she approached a student who had his head on his desk. Even though he was a very good student, he didn’t want to talk about high school. All he would say is “I can’t go to ninth grade. I’m not going to ninth grade. I won’t go.” He wouldn’t explain.
When the principal took him aside took him aside, he told her why: “I can’t go to high school because I live in a car with my Mom, and I don’t have a place to wash my clothes or take a shower.” He was very embarrassed.
Keep in mind that this a true story.
That principal told him, firmly, that he was coming to ninth grade at her high school, and she told him how she would make that happen. Every day, she took an extra uniform home and washed it so he would have a clean one for the next day. And every morning she made sure that he could use the tiny bathroom near her office to wash up before school.
He is a senior now. He has dreams for his future. He didn’t drop out. He did not become a statistic. This is the most powerful example of extra support that I have ever seen.
Reflecting on your career, what would you say was your greatest professional learning experience, and how do you use it to help vulnerable children live up to their full potential?
I spent 17 years as the CEO of the Detroit Girl Scout Council, and we developed a teenage pregnancy prevention program. This was very a controversial move in this 1980s. It just wasn’t done back then.
One of our funders called to ask me why it was necessary, and I told him that it is because every girl has a uterus. Every girl needs awareness and education about her body. Every girl has the right know how not to end up pregnant at 12 or 14 years old.
Working at this taught me a lot about tenacity and patience. I also, learned that no matter how hard, it is very important to listen to others’ points of view. We were successful. This is one of my greatest achievements.
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Program Profile


  • City Year Detroit
    City Year’s mission is to build democracy through citizen service, civic leadership and social entrepreneurship. It is through service that we can demonstrate the power and idealism of young people, engage citizens to benefit the common good, ...


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