Don’t Be Afraid to Break Things

Sep 18, 2025 | Grant Writing

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The idea of failure used to scare the living daylights out of me. And admitting a mistake. Hard pass; no thank you. Zero stars. Do not recommend.

It was the perfectionist in me. I never wanted to show a single flaw or misstep. Heck, I wouldn’t leave the house without hair and makeup styled. I worried way too much about what others thought about it.

Then I reached my 40s and realized that life is too short to worry about all the things. And suddenly I found myself focused more on finding joy and less worrying about others. Understanding that the mistakes taught me important life lessons. And admitting my mistakes allowed me to move on from them. And sharing my mistakes with others made me human and helped others from making the same mistakes. It’s a freeing thing.

It’s in this vein of being unafraid to make mistakes, try new things, and go against the grain that we wanted to talk to Stacy Fitzsimmons. She has a fantastic take on leadership, going out on a limb, breaking things, learning, and starting the cycle all over again. You can listen to that episode of Fundraising HayDay HERE.

If my friend Julie Boll has taught me anything, it’s that naming things helps take away its power. That’s why it’s so important for us to break away from the “well this is how we’ve always done it” mentality.

Here are some things I’d like to name and then work to make better.

  • Many funders ask for agencies to implement tried and true, evidence-based practices. And while that isn’t a bad thing, it doesn’t mean those are the only programs that work. Organizations should have the room to say: we have implemented the tried-and-true methods, but they don’t work for our community, which is why we are trying something new. I mean, how did we get tried and true methods in the first place? Someone led the charge to a new way of thinking and working. Let’s give our changemakers room to keep changing as needed.
  • We must aim for the perfect application. Really? What’s more important – solving an issue in a community or having all your commas in the correct place. As a grant reviewer I have often felt like my hands were tied over the scoring process. There were grantees who clearly had the greatest need for funding, but because they didn’t have a seasoned grant professional on their team, their applications were not as savvy as others. There must be a way for funders to work with applicants to ensure the greatest need comes through and has equal chance of being awarded grant funding.
  • We can’t tell funders how we really feel about them. Listen, I get it. Funders hold the power of the purse, which gives them a lot of power. But their processes are not always fair, equitable, or even realistic. Their application portals can be difficult to navigate, they often don’t provide contact information so there is no one to contact with questions, and they sometimes provide such limited information on who and what they fund that your proposal feels like a shot in the dark. If I was queen for a day, I’d require every funder to have a website with detailed information, an email address they responded to within 48 hours, and an open call for ways to improve their processes (with no repercussions to grantees who have suggestions).
  • Grant professionals are quick to share what works, but often shy away from admitting what didn’t. I get it. The fear of judgement and repercussion is powerful and painful. But I wish we were more willing to share our flaws. Because these discussions only benefit the next generation of grant pros. You missed a deadline? Guess what – you’re human. Your success rate this year is 40%? Chances are you went after some big-time grants that had a high competition – way to stretch yourself!

Kimberly and I feel so strongly about talking about all aspects of the grant profession that we started a monthly “Mistakes Were Made” episode on our Patreon. If you join at our Heavenly HayDays membership level you can tune in.

Obviously, we don’t want our work or life to be so full of mistakes that we don’t have any wins. But it’s the mistakes, lessons learned, and ability to keep trying that make the wins bigger and better in the long run. So go out and break things. And let us know all about it by emailing hello@haydayservices.com.

Amanda Day
Fundraising HayDay

A podcast about grants & such.

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