How I Overcame Fundraising Dread

A moment of transparency— fundraising used to give me the cold sweats. You’d think I was auditioning for a horror movie! Sure, raising money is crucial in nonprofits, but asking folks for cash felt like trying to pet a porcupine. It took time, growth, and a lot of reflection for me to see fundraising differently.

This change didn’t happen overnight, but the breakthrough came during our 10th Year Behind the Mask Gala. What started as an event to raise money turned into so much more — it became an opportunity to connect deeply with people, build community, and rally around a cause we all believe in. And the results? Beyond what I ever expected! We not only exceeded our fundraising goals but created lasting relationships with people who are just as passionate about our mission as we are.

Why Did It Feel Daunting?

The thought of approaching people for money felt foreign and I worried they would think I was only interested in their wallets. I had acquaintances that seemed like they were always selling something and I avoid them like the plague. How could I now ask for funds without feeling awkward?

Of course, I feared people would picture me as their least favorite telemarketer. I have never been interested in transactional dynamics; I value authentic connections. I also knew I needed to ask if I wanted our nonprofit to grow and help more people. It felt like an impossible situation.

I worried that people would say no — or worse reject me personally. It’s something I struggled with for a long time. (Like the first full decade of nonprofit leadership!)

A Plot Twist

The big shift came when I realized something simple but profound: fundraising isn’t about asking for money. It’s about advocating for the cause I’m so passionate about — our students, our programs, and the lives we’re changing every day at iCan Dream Center NFP .

I had to alter my thinking. Instead of feeling like I was imposing on people, I began to see it as an opportunity to share the amazing things we were doing and invite others to be a part of it. Afterall, I wasn’t asking for money for myself—I was speaking for those who need our programs most. Once I started advocating for them instead of focusing on the fundraising numbers, the conversations felt much more natural. At that point, it stopped being about "the ask" and started to be about connection. I was connecting people to something bigger than any one of us.

I don’t have relationships with donors, I have relationships with people who are also invested in this cause.I knew that the real magic happened when...

?? Fundraising began to feel less like requesting a favor and more like inviting people to be part of something meaningful that truly makes a difference in the world.

?? The relationships I have developed remained authentic and were not limited to raising funds.

?? People didn't just leave our events entertained—they left inspired to get involved in even bigger ways!

Our upcoming Fashion Show Gala celebrates fashion, community, and the incredible impact we’re making together. It’s more than a fundraiser; it’s an event where you can have fun, meet like-minded people, and contribute to moving our mission forward.This year, we’re kicking off Chicago Fashion Week!?? Expect a glamorous evening filled with fashion, delicious food, great company, and plenty of fun. But even more than that, expect to leave feeling inspired — knowing you’ve helped make a difference for neurodiverse learners.

Purchase your tickets today!

I can’t wait to see you at the Fashion Show, where we’ll celebrate the incredible change we’re creating in the world!