When the Startup Becomes the System: Knowing When to Move On

It’s been just over nine years since I left Stupid Cancer. Some days, it feels like a lifetime ago. Other days, like yesterday.

There’s a moment in every startup or early-stage nonprofit when the chaos starts to calm. When whiteboards become roadmaps, Slack turns into org charts, and the gritty, figure-it-out hustle gives way to polished processes and official departments.

For some, it’s a long-awaited relief. For others—people like me—it’s a sign.

I joined Stupid Cancer (fka i[2]y - I’m Too Young For This! Cancer Foundation) when it was scrappy. Our ideas outpaced our resources, our passion outran our capacity, and we thrived in the unknown. I wore every hat, from operations and events to tech and merchandise. One month I was leading a 10-city road trip; the next I was negotiating vendor contracts or troubleshooting a donation form at midnight. It was unpredictable, unscalable—and I loved it.

But as we grew, something shifted. We built structure. We added roles and layers. Things that used to be a quick chat became committee decisions. Processes got cleaner—but also slower. We were doing the right things for a maturing organization. And I was proud of that growth. I had helped build it.

Still, I started to feel it in my gut: this wasn't the same work anymore.

I realized I was more comfortable in the ambiguity. I thrived when we were making it up as we went, when the mission and the hustle were inseparable. I was energized by building, solving, and stretching. But in the newly formalized environment, I felt like I was maintaining, not creating. There was less space for improvisation. Less mess to clean up. Less adrenaline.

That’s when I knew it was time.

Leaving wasn’t easy. Stupid Cancer was family. It shaped who I was as a professional and as a person. But staying would have meant resisting the very progress we had worked so hard to achieve.

I find purpose in uncertainty, in figuring it out before it’s figured out. And that’s not something to fight—it’s something to follow.

So, I stepped away. Not because I didn’t believe in the mission anymore, but because I had helped bring it to a place where someone else—someone better suited to stability—could take it further.

Nine years later, that decision still feels right.

P.S. No matter where I go or what I build next, I will always carry a deep love for Stupid Cancer. It’s in my DNA. The mission, the people, the memories—they travel with me. Always. Make a donation, here.