Five Years, Five Lessons: What Leading Aspire Has Taught Me

By Paula Fynboh, CEO, Aspire Afterschool Learning

I was scared to take this job.

Not because I didn’t want it. But because for a long time, I had been told that it wasn’t realistic to be the kind of leader I wanted to be. That leading with values was too idealistic or rigid. That the voices of the people closest to the work were too tactical to shape strategy.

And for longer than I’d like to admit, I believed them. I passed up two promotions because I didn’t think my leadership style was cut out for senior leadership. I had often been told that my values of equity and joy were in competition with growth and impact.

Five years ago, I chose differently.

This summer, I celebrated my five year anniversary with Aspire Afterschool Learning as CEO, and I’m not going to pretend I have it all figured out. I’ve made mistakes (and will continue to do so). I’ve cried in my car, collecting myself before walking in to face something difficult. But I’ve also had the profound privilege of watching students fall in love with learning, of seeing families supported with dignity, and of building something alongside a team and a board that has restored my faith in what values-driven leadership can actually look like in practice.

These are five things I’ve learned.

Lesson 1: Build the Culture First, Then the Tools Will Work

When I became CEO, one of my first and most important responsibilities was to work with the Aspire community to build a tool to take our newly adopted values from words into action. But here’s what I learned quickly: the tool was never going to be enough on its own. What made it work was the culture we would build together.

I came in with a Values in Decision-Making Scorecard, adapted from RACE Forward’s Equity Impact Tool. I’ll be honest, I expected pushback. In my previous work, tools like this were dismissed as too rigid, too slow, too idealistic. So, when I brought the scorecard to the Aspire board and it passed — not without thoughtful discussion, but without resistance — it almost felt too easy.

But I realized it wasn’t easy. It was alignment.

The board understood, as I did, that adopting organizational values means taking responsibility to ensure they are operationalized at every level. They were ready to govern with our values, to hold themselves to the same standards we hold staff, and to make accountability to our community transparent in how we listen, make decisions, and show up. I wasn’t just getting permission to use a tool I believed in. I was joining a culture that wanted the same thing and that not only understood, but believed deeply that equity and impact and joy and results were not in competition with one another, but rather essential to each other.

Over these five years, we’ve used that scorecard for everything: curriculum decisions, budget line items, hiring, partnerships, and yes, even chicken nuggets (our students put them on the strategic plan and we ran them through the scorecard, which helped us balance healthy eating with keeping learning joyful). What I’ve learned is that the scorecard matters, but only because the people using it are genuinely committed to what it stands for.

The lesson: Values are only as real as the decisions they shape. Build the tools, but invest even more in building a culture willing to use them honestly.

Lesson 2: Hope and Joy Are a Strategy

There is a particular kind of exhaustion that comes from working in systems change. On any given day, we are greeted with heartbreak, and what we care about most is under attack. In that exhaustion, joy and hope can start to feel elusive, even like toxic positivity.

But I want to push back on that. Hard.

Hope and joy are load-bearing walls. A child cannot learn in a space where they don’t feel safe, seen, and welcomed. Joy is the precondition for growth, and we see 67+% of our students improve in reading and math each year. This doesn’t happen because we force learning into them. It happens because they know we believe in them and we’re here for them. Last spring, we lost over one-third of our budget overnight to federal funding cuts. I pulled into the parking lot the next morning knowing I had to tell our teachers their positions had been eliminated. I didn’t know yet how we would rebuild. But I knew what we had built over years, a culture of joy so real and so deeply felt, would carry us through the hardest weeks of my tenure. Our classrooms still echoed with laughter. Our students organized a lemonade stand to help, not because we asked them to, but because they understood that Aspire was theirs. Within five days, our community had rallied enough support to hire back nearly all of our teachers.

That investment in joy is what held us together.

In a world asking a great deal of young people right now and where our kiddos are navigating unprecedented uncertainty, grief, and a future that feels scary, choosing to protect hope and joy is one of the most important decisions a leader can make… and it is strategic. Aspire’s ethos is the foundation for our relationships. From there we can build strategy, fundraising efforts, staff models, and more. It’s the combination of these factors that made it possible to fill the initial AmeriCorps funding gap and maintain our programming despite devastating cuts.  

The lesson: Don’t make your community experience joy as a luxury. Lead with it. Protect it fiercely. It will carry you further than you think.

Lesson 3: The People Closest to the Work Are Holding the Most Important Knowledge and the Process Is the Product

Early in my career, I was a front-line community organizer. We were about to send out an action alert, and I knew from the conversations I was having in the community it was the wrong ask to the wrong list. I told my manager. He told me I was thinking too tactically and too small. We sent the alert anyway and we spent the next three days cleaning up the mess instead of doing the real work.

That lesson has never left me.

When I joined Aspire, the board asked me to develop a strategic plan to grow the number of students we served. My strategy for the first six months? Listening. Deeply and intentionally to staff about what it actually took to run and grow an effective program, what was working, what was getting in the way, and what resources and ideas were needed to get there.

That listening shaped everything. We built our first three-year strategic plan together, with the expertise of front-line staff, our students, and our community, and by the end of it, we had more than doubled the students we served and our fundraising budget, and we did so without compromising program quality and keeping our programs at no cost.

This approach is not just reserved for the big strategic moments, but is integrated in all of our decision making. For example, when a budget crunch put field trips on the potential chopping block, our Program Director Anna pushed back. She walked me through what field trips meant for kids who live just seven miles from the monuments and museums of Washington, D.C., but who rarely venture beyond the mile radius around their homes. She talked about the vocabulary, exposure, and a child’s sense of what is possible for them. I kept the field trips.

I’ve come to understand that the process of listening, co-creating, and building trust is not just a means to an end. As I like to say, “the process is the product.” The relationships built in that listening, the expertise surfaced when staff, young people, and families are genuinely heard, the ownership created when people help shape what they’re being asked to carry… that is the work.

Investing in staff, their wages, their wellbeing, and their ability to stay is not separate from serving students well. It is the same thing. High turnover doesn’t just destabilize programs. It breaks the relational continuity that makes our model work. Students who have a teacher they love and trust shouldn’t have to start over every year.

The lesson: Lived experience is an expertise. Invest in and treat it that way. If you want people to show up for you in a crisis, show up for them first because the process is the product.

Lesson 4: When You Center Students and Families, They Will Show You the Way

I think about José a lot.

José aged out of Aspire and, through our growing STEM programming and expanding partnerships, we connected him with a pipeline program now putting him on track to be the first person in his family to go to college. When we told his mom he was accepted into this program, she started crying and asked: “Why me?”

Not “I knew he could do it,” but why me.

Those two words tell you everything about what it means to raise a child who has been systematically underestimated. They also tell you everything about why this work is so urgent.

As early as sixth grade, students are being asked to choose electives. If they haven’t had exposure to STEM, to building things, to being curious without fear of getting it wrong, and to knowing someone believes in them and sees their potential, those doors can close to historically underserved students before they even knew they were open. For first-generation students, early access and exposure is often the difference between a path forward and a blocked path. 

I think about Mario too, who wanted to skip soccer practice to keep working on a worm farm science project, and about Octavia’s mom, who went out and bought her a chess set after she fell in love with chess at Aspire because she had never seen her so excited about something like that before.

Centering students and families means letting what you hear from them actually shape what you do. Moving into Title 1 schools was rooted in this principle. We don’t ask families to come to us across logistical barriers; we go to where they are. We keep our programs at no cost, always, because the ability to pay should never determine the ability to access high-quality afterschool programming, or rad at grade level, or be safe after school. And we continually respond to feedback and input from our families. We built a makerspace. We developed a food pantry. We hired a bilingual Parent Engagement Coordinator who is the parent of an Aspire alum, because the families we serve deserve to be seen by someone who knows what their life actually feels like.

One of the most persistent drivers of educational inequity is lower expectations for low-income Black and Latinx kids. Centering community is a statement about whose curiosity is worth investing in and whose experiences and expertise is worth listening to.

The lesson: Build partnerships, not charity. Ask. Listen. Let the answers guide what you do, and then do it.

Lesson 5: The Future Belongs to Kindness and Curiosity

I hear a lot of fear right now about the future. Technology and AI are accelerating change faster than our institutions were built to absorb, and the anxiety is real.

But here is what I believe: tools change, whether it it’s the fax machine, email, smart phones, or now, AI. What has always mattered, and what no tool can replace, is humanity. Empathy. Kindness. Curiosity. Critical thinking. The willingness to sit with complexity without rushing to false certainty and the ability to see each other as human.

If we teach kids to ask good questions and evaluate evidence, they will know how to use any tool wisely, including AI. If we teach them curiosity, they will keep learning no matter how fast the landscape shifts. If we give them real confidence, the kind that comes from being believed in, challenged, and seen, they will not be displaced by technology. They will shape it. And if we teach them kindness, they will use tools in a way that creates a better world.

That is why our 2025–2030 strategic roadmap includes a logic curriculum for critical thinking, expanded social-emotional learning, STEM programming, and a makerspace designed to spark curiosity.

The lesson: Prepare kids for the future, not just the test. Bet on their humanity; it is the most durable thing they have.

Looking Forward

Over the last five years, we have more than doubled our student enrollment without sacrificing impact or quality, we kept our programming at no cost, and we rebuilt from losing over one-third of our funding overnight. We have a new five-year strategic roadmap, the most ambitious and community-rooted plan we have ever had, built with students, families, staff, board, and community partners.

We got here by operationalizing our values, building a culture of hope and joy, investing in staff and listening to those closest to the work, and centering the students and families we are here to serve.

And just like our students, I am still learning. Every day. And I hope I always will.

I am grateful beyond words for the Aspire community, for the students who trust us with their curiosity, the families who trust us with their children, the staff who trust me with their livelihoods and their whole selves, a board that trusted me when I was new, and our supporters and partners who invest their time and resources to make our work possible.

To everyone who has been part of this journey: you are the reason Aspire echoes with laughter. You are the reason a mom asks “why me?” in the best possible way. You are the reason I am a better leader.

Thank you.