Wearing Multiple Hats: My reality of leading a nonprofit

Nadine Machkovech
Aug 22
6 min read

After almost 12 years in this world, I’ve learned that grassroots nonprofit leadership isn’t really about titles. It’s about hats. Too many hats, worn all at once. Leader, fundraiser, advocate, admin, accountant, cheerleader, problem-solver. Some fit, some don’t. But when the mission matters, you put them on anyway, even when the weight of them leaves a permanent mark.

People love to toss around titles like CEO, Executive Director, Founder, Program Manager... but the reality is, in a small nonprofit, titles don’t always matter much. What matters are the hats you wear, and in this world, you end up wearing a lot of them.

Loss and Leadership

When I started with RISE Together, I wasn’t new to leading; I was new to leading a nonprofit. But I knew how to coordinate, lead teams, and connect with people in ways that created real change.

In 2018, we became a 501(c)(3) so we could expand our work beyond the stage and provide ongoing support for young people who needed more than just a one-time presentation.

A year later, everything turned upside down.

One cofounder separated from the organization. And shortly after that, our other cofounder, Anthony, my partner and the love of my life, lost his son to the very thing we were working to prevent. A fentanyl poisoning that rocked our world to the core.

And COVID hit, forcing us to temporarily close our doors. The mission we had poured everything into suddenly felt fragile, and survival was uncertain.

In the middle of that grief and chaos, Anthony stepped back from his role, unsure if he’d ever speak on stage again. My board voted me in as Executive Director. Overnight, I went from operations to carrying the entire mission and all of its weight on my shoulders.

For the past 5 years, I didn’t just keep the lights on. I fought tooth and nail for every contract, every grant, every opportunity to keep our programs alive. I carried the grief, the leadership, the work, and the hope for what this could still become. And I couldn’t have done it without the support of my community.

Breaking the Myths

There’s a romanticized idea about running a nonprofit. But here’s a list you don’t see in the brochures:

It’s not easier because it’s “nonprofit.” Every dollar is earned through grants, donations, contracts, or fundraising events.
Funding is a full-time job. Schools rarely have budgets for outside programs unless they’re “evidence-based,” and becoming evidence-based can take years.
Passion isn’t enough. It takes relentless persistence, unglamorous admin work, and the ability to hear “no” more times than you ever thought possible.

And yes, there’s bias. I once sat on a call with a prominent family foundation where someone asked what made our program “credible” since I don’t have letters after my name. At the time it stung, but it also reminded me that lived experience is its own kind of credential, and I’ll never stop standing on that truth.

Thankfully, we’re on the evidence-based track. For over six years, we’ve partnered with Penn State College of Medicine, and all our programs are data-supported. But that came only after years of writing proposals at midnight, chasing funding like it was oxygen, and stretching one month’s budget to survive the next.

Not Everyone Can Do What We Do

This past spring, we sent trained leaders into a school close to our hearts to speak on our behalf. It didn’t go as planned. The feedback from teachers was humbling and tough to hear.

It was a painful reminder that not everyone can hold space for youth the way we can. It’s not about charisma, it’s about connection, trust, and lived experience.

And that’s been one of our biggest challenges: people want us. They want Anthony and me in the room. Which makes our model hard to scale but also confirms that what we do is unique and deeply needed.

Growing to Serve More People

So we had to grow.

If we can’t be everywhere for the youth, then who can we serve?

Since 2020 we began to also focus on peer adults like teachers, youth educators, and mentors. Equipping them to create the same kind of safe spaces we’ve been building for years. If we can train and support them, they can carry the work forward where we can’t.

It hasn’t been easy. Volunteers are hard to come by. Asking teachers to do more when they’re already stretched thin is a big ask. And yet, the community has continued to show up in incredible ways. Still, the need is greater than what one small nonprofit can meet.

Why I’m Still Here (and Why Wisconsin Is Still Home)

As we head into our golden anniversary next month, it’s hitting me just how far we’ve come and how much we’ve fought to keep this mission alive.

RISE will always remain a nonprofit rooted in Wisconsin. That’s where this mission was born, and it’s still where our team shows up for young people, families, and communities every single day. Wisconsin is home. Not just because it’s where our friends and family are, but because it’s where so many people continue to fight alongside us.

And yet, this work has taken everything out of us at times. We've worked so hard towards the mission and even had to have many side gigs to support it.

The late nights. The early mornings. The constant grant writing. The endless cycle of asking for support. The bullies. The people who tried to walk over us. The ones who used us for their own agenda. The whispers. The assumptions.

And I know I’m not alone. I’ve watched so many in this space become compassion fatigued, worn down by the endless cycle of giving more than they get, overworked and overwhelmed by the very mission they set out to serve. I’ve seen good people burn out and walk away, not because they didn’t care but because caring cost them too much.

It’s exhausting.

It’s heartbreaking.

And it’s the reality nobody likes to talk about.

Anthony and I have given more of ourselves to this work than we ever thought possible. Our time. Our energy. Our financial stability. Even pieces of our own health. We’ve missed family moments. We’ve carried grief on stage. We’ve shown up when our personal lives were falling apart. Because we believed the mission mattered that much.

But since becoming parents together, we’ve realized what’s most important: showing up together, as a family, in ways that are sustainable and true. When Anthony and I step on stage now, it’s not just about sharing our stories... it’s about standing side by side, leading from a place of authenticity, grief, resilience, and love. It’s about modeling what healing and growth can look like, even in the middle of the hard.

And I’ve also seen the other side. I’ve seen the faces of students who finally exhaled because they felt safe enough to share their truth. I’ve read the messages from young people who said our story kept them alive one more night. I’ve watched entire rooms shift when someone realized they weren’t alone in their struggle.

Those moments are sacred.

They remind me this isn’t just about programs or grants or nonprofit titles. This is about lives. About kids breaking generational cycles, fighting for their mental health, and learning that their voices matter.

That’s why I’m still here.

Not because it’s easy. Not because it pays well. But because I’ve seen the power of a safe space, of a story, of someone who believes in you.

And I can’t and will not walk away from that.

Your Part in This Story

If you believe in this work... if you believe our youth deserve better, here’s how you can help:

Share this blog so more people understand the reality behind the mission.
Invite us to speak in your school, workplace, or community.
Make a donation so we can keep showing up where we’re needed most.
Come to RISE 12 and celebrate our golden anniversary with music, laughter, and community. (Use the special discount code RISEFAM for 50% off your ticket)