10 Asks in 10 Days Challenge

This episode is a little different—it's a snippet from a coaching call where we dive deep into the "Ten Asks in Ten Days" challenge. If you’ve ever struggled with making bold asks, whether in fundraising, business, or life, this one’s for you.

I started my business nearly seven years ago because I saw so many smart, relationally savvy leaders who were “stuck”—not because they lacked strategy, but because they lacked courage. I kept hearing, “I need a better strategy,” but what I realized? Strategy wasn’t the issue. People just weren’t taking action. They weren’t making the ask.

So, I became a student of courage. I read, I studied, I surrounded myself with bold people, and I learned that courage isn’t something that just “happens”—it’s built. It’s designed. And it’s necessary if we’re going to do the work that actually moves the needle.

Why We Don’t Ask (And Why That Needs to Change) 

I can’t tell you how many times I’ve heard, “I’m just not comfortable asking for that amount.” And let me be real with you—that both breaks my heart and fires me up. If we want to raise millions, build reserves, and truly change our communities, we need to get past our discomfort. Because courage isn’t about confidence. It’s about taking risks “even when” confidence isn’t there.

The Ten Asks in Ten Days Challenge

Here’s the deal: Over the next 10 business days, you’re going to make 10 asks.

- These can be professional or personal. Maybe you’re asking a donor for a $10K+ gift. Maybe you’re asking your partner for support. Maybe you’re asking a board member to step up.

- The goal? Push yourself outside your comfort zone. If your asks don’t make you at least a little sweaty, you’re playing too safe.

The key? Stay curious. Drop the defense. Listen more than you talk. And when it comes to those big asks—don’t wait until the last minute. Start now.

What’s Next?  

1. Write down your 10 asks—who you're asking, what you're asking for, and when you’ll do it.

2. Commit to taking action. This is a “risk sprint”—it should stretch you.

3. Be prepared to be “surprised” by how people show up for you.

So, are you in? Let’s make some bold moves. Listen in for the full conversation and let’s get to work!

Want 15 leads in 5 minutes? DM me "Breakfast burrito" on LinkedIn and I'll send you a pdf and 6-minute training to help you generate 15 leads for your nonprofit in minutes. It's totally free. All you need is an email to sign up. DM me "Breakfast burrito" - I'm from Texas, what can I say? - to get your pdf and mini training. 

If you're an org with at least $800k annual budget and major gifts is your top priority, but you need a better strategy and approach, get on the waitlist for the next CourageLab cohort here: https://julieordonez.kit.com/couragelab2