S5 Ep. 8: 10 Asks in 10 Days Challenge

S5 Ep. 8 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!

Quotes from the episode 

“ Courage is the risks that we take on behalf of others. It is the choices that we make, not the words that we say, but the choices that we make and the risks that we willingly take that we put our neck on the line, literally.”

“ You're going to be surprised at your own courage and boldness.  It's going to feel good.”

“ It takes courage to stay curious and not defend yourself. Not try to explain, not try to be understood, but rather to understand. This happens with questions.”

“  It's not your job to budget his philanthropy. It's your job to raise the money.”