Jason Cascarino: Expert Spotlight Throwback
We are incredibly excited to shine a light on Jason Cascarino, a veteran executive in the social sector, particularly within the education and youth-serving spaces and a Citizen Schools alum. For over twenty-five years, Jason has consistently driven impact through leadership roles in prominent philanthropies and nonprofits across Washington D.C., Boston, and Chicago. For the past eight years, he has served as a highly sought-after strategic advisor and consultant, guiding numerous local and national organizations in crucial areas such as business strategy, program design, financial modeling, and impact measurement. His executive experience includes serving as CEO of Spark Program, which tripled the number of students served across five school systems during his tenure, and as COO of The Chicago Public Education Fund, where he led a partnership with Chicago Public Schools to develop its first-ever comprehensive human capital strategy. Jason's wide-ranging work leading and strengthening education and youth-serving organizations gives him a valuable lens in this space, and we can't wait for you to hear some of his insights.
What does Experiential Learning (EL) mean to you, and why is it important? What would it look like to truly learn experientially? We often equate learning with schooling and then we equate schooling with academics, which is very didactic in traditional education classrooms, not really experiential. Certainly, there is some learning that we get from books, lectures, and even TV and movies, but a lot of learning especially when focused more broadly on human development is through experience. I think experiential learning looks like teachers and students doing a lot of co-creating and teachers acting as facilitators. Teachers would bring everyday life into academic settings by setting up concepts, ideas, methods, and practices and allowing students to absorb them by playing with them, applying them, and failing and iterating.
I've been a big believer that youth engagement in learning is one of the fundamental deficits that we're currently experiencing in public education. You can see it in the data, especially around the middle grades, which has been identified as a pivot point in human development and learning. Engagement starts out relatively high in elementary school, then it significantly drops in the middle grades, and then it levels off in high school while never regaining any ground. Once young people check out, they aren't going to learn very well. We experience this all the time as adults. If we're checked out in a conversation, or an activity, or in our jobs, we aren't taking anything of value or learning and we aren't productive. I think the special power of experiential learning is in its potential to boost engagement across the board, and with that, I think greater learning, greater achievement, and even greater happiness comes. We see kids wanting to go to school because of their after-school activity, or their sports, or because of that one class that has a specific spark to it. That’s why they come. They kind of muster through the rest, but it's that one driving thing that really hooks them. If that hook was pervasive throughout the day I think education would be a different experience for young people and we’d see better outcomes.
What do you believe is the best first step towards advancing the future of learning? What is necessary to make it successful? I've spent more than a couple decades in this space, so I have a lot of battle scars and war wounds that are connected to some version of this question. There are three specific things I would point to.
First, I have a bias toward talent. I think great talent in schools and in youth programs really makes all the difference. You can have an amazing in-school curriculum or out-of-school programming, but if you don't have highly capable and engaged adults to deliver it, it's less likely to succeed. Conversely, if you have subpar programming, curriculum, or resources, but you have top talent working with it, they usually will make the best use of it and turn it into something that is effective. In my work with the Chicago Public Education Fund, we invested in talent as a core lever of change. In education, you can't fund it all or tackle it all. You have to pick your spots. Talent is a pivotal spot.
The second point to tackle is transition points. Some transitions, like when kids go into kindergarten, we've made a lot of progress with – in that case with more Pre-K learning. Entry into post-secondary and the workforce, people are doing good work on those as well. Entry into middle grades, we’ve done little systemically as a field and even entry into high school is under-addressed. I think it is these transition points where we lose a lot of kids. We see in the data, even kids who were successful in one period, they can easily be knocked off course in the next because they didn't transition well. When you transition, you have to establish new sets of relationships, new ways of doing, new ways of behaving, new routines, etcetera. That can knock kids off course. I think being very intentional about these pass offs no matter where they are on the educational continuum is essential to focus on.
The third one I would say is I think we need education to better map onto human development. Students are children and young people first and foremost. The more that learning environments and experiences are tailored to the developmental stage they are in and the developmental needs they have, I think the more successful that education will be. I spend a lot of time in the adolescent space these days - stemming first from my Citizen Schools experience - both in middle school and in high school and into post-secondary. Adolescence as a stage in human development is a time of self-discovery and identity formation and building self-worth and self-efficacy. The more our learning environments and experiences are set up to sync with those things, I think the more successful young people will learn. They'll stay engaged, they'll feel included, they'll feel heard, they'll feel a sense of ownership over their own trajectory.
Who is the most influential mentor you have had throughout your life? What qualities did they impart that you continue to embody in your work? There are a lot of informal mentors and family members that come to mind. There are three whose teachings I have carried with me almost on a daily basis.
The first is my high school golf coach, Mr. Witter. Here again, very experiential, out on the golf course, and very organic. He emphasized visualization and how so much of sports is mentality and how you think about yourself and your performance. Visualizing the shot in golf or getting a hit in baseball or what have you. One big component of that is positive thinking. He used to talk about the “pink elephant theory.” He would say that if you tell someone not to think about a pink elephant, the first thing they think of is a pink elephant. So, if you're standing on a golf tee and you're thinking “don't hit it out of bounds, don't hit it out of bounds,” the most likely thing is you're going to hit it out of bounds, because that’s what you’re thinking about, avoiding the negative. Instead, you should think "hit it down the middle of the fairway.” The whole idea is to be focused on the positive or ideal outcome of whatever action that you're taking. I use that in my consulting work right now, and in everyday life, not successfully all the time, but certainly as a philosophy.
The second was a professor that I had in college, Dr. Parente. He was the one that really helped me hone my skills around how to think, how to analyze, and how to tackle problems successfully. He taught me how to understand complex issues and distill them. I think I became good at taking lots of different factors and inputs and putting them into frameworks that are digestible and understandable. That kind of analytical ability, the ability to attack problems, the ability to think and analyze. I first learned how to do those things from him and now I apply them as second nature.
The last one was my first boss, Dean Millot, when I worked at New American Schools in DC. It was my first real job, and I learned from him how to apply my skills to different contexts and domains. We both came out of national security and international affairs and had pivoted to the social sector. He was able to impart the concept of translating your skills into different spaces, which I feel has helped me be adaptable. Today, I take on clients, not only in the education and youth space, but other domains as well. I feel confident in being able to make some kind of impact and help folks in different domains without needing to be an expert in the particular content or subject matter of whatever the organization does. I feel like I can facilitate their thinking, their subject-matter expertise, around strategy and program outcomes.
Can you share an experience you had mobilizing your community through Experiential Learning? What do believe allowed for this to be successful? I've had two major professional experiences with Experiential Learning, one with Citizen Schools and then I had the opportunity to lead an organization called Spark. Both were designed with very similar themes around apprenticeships, middle school age kids, and mentoring.
Most recently, I've had the opportunity to serve on the board of my local education foundation here in Oak Park, Illinois, the Oak Park Education Foundation. Unlike other education foundations, it doesn't give away money. Instead, we offer programming in the community that is very experiential. We offer summer programming and also have a variety of programs that push into school classrooms.
One of the challenges that we have is that programming is only as successful as the people and organizations that deliver them. We focus a lot on how to get this programming that we know is effective into the hands of people that need it and do that in a way that is of high quality, is scalable, and ultimately sustainable. Some of the most important things I work on are not on the programming side but more on the organization side. By that I mean building the operational structures and capacities so that the organization can deliver results, engage the community, and provide value.
I’ve found that funders especially want to fund programs and have that immediate impact, or immediate sense that the money is going directly to the folks who need it. But, in my mind, it really comes down to the organizations and the people that run them and work for them, not just the programming by itself, that drives results and makes good use of that funding.
Data-driven results are instrumental in helping to share success with outside stakeholders. How has your organization/school etc. been able to reflect your results effectively? What challenges have you encountered in the process? As a consultant now, I work with a lot of clients on this very topic. Whenever my colleagues and I work with organizations on strategy, the process is always centered first and foremost on the outcomes. There are a couple big pieces to this that I would highlight. First, at any organization folks have a particular role to play and are most engaged day to day on their tasks. But at the end of the day, what are all those tasks for? We try to direct our clients more toward the outcomes as opposed to the outputs. You provide hundreds of hours of engaging out-of-school programming for young people. Great! That’s an output of your work. But the outcome you are driving is improving learning and development for those young people. In some cases, it can take a long time for folks to make the shift toward the outcomes they really want to drive versus just the outputs they are producing and the activities they are doing, but they get there. Second, I think it’s important to match your outcomes to your capacity. If you don't have the capacity to deliver results, then your intended outcomes are more like aspirations. So, successfully calibrating outcomes and capacity is a big challenge for many nonprofits. Aspirations are great – they are motivating. But, most of us in the education and youth-serving space are really in this business to actually make meaningful change.