Boost Your Fundraising confidence By Stepping Outside Your Comfort Zone
Fundraising is not for the faint of heart. It requires taking risks, asking for what you want, and embracing the possibility of rejection. The more you can get comfortable with discomfort, the more powerful you’ll become as a fundraiser.
I recently had a moment of discomfort myself—standing in front of a crowd at karaoke, debating whether to sing a song I had never performed before. It might seem like a simple decision, but the experience revealed a lot about overcoming fear, releasing expectations, and stepping into confidence—lessons that directly apply to fundraising.
Why Fundraising Confidence Comes from Discomfort
Fundraising is about more than just asking for donations; it’s about relationship-building, making bold requests, and facing potential rejection. Yet, many fundraisers hesitate because of fear. Fear of the ask. Fear of hearing “no.” Fear of not getting it right.
But here’s the truth: growth comes from discomfort. Just like stepping up to a karaoke mic despite nerves, stepping into fundraising courage requires pushing past fear and taking action anyway.
Six Ways to Build Fundraising Confidence (Lessons from a Karaoke Mic)
1. Release the Outcome
One of the biggest lessons I’ve learned—both in karaoke and in fundraising—is to let go of the result.
If I had been too attached to singing perfectly, I never would have gotten up there. And if you’re too attached to securing a “yes” from every donor, you’ll struggle to make the ask in the first place.
When we release the outcome, we:
Act from confidence rather than fear
Stay open to unexpected opportunities
Build stronger, more authentic connections
In fundraising, a “no” might lead to a future “yes” in a different form. When we’re not fixated on a single result, we open the door for greater possibilities.
2. Give Yourself Permission to Be Bad Before You’re Good
Fundraisers often expect to be great at asking for money from day one. But just like learning a new song, fundraising takes practice.
As my friend Sonia Sala says, “You have to give yourself permission to be bad so you can be good. And then give yourself permission to be good so you can be great.”
When I stepped up to sing that song, I accepted that I might mess it up. That’s the same mindset fundraisers need—embrace the learning curve, knowing that every ask builds your confidence and skill.
3. Separate Facts from Feelings
When I was nervous about singing, my brain told me, “Everyone is watching. If I mess up, it will be a disaster.” But the reality? No one was paying that much attention.
Fundraising fears often come from emotion rather than reality. If you’re nervous about calling a donor, ask yourself:
What are the actual facts?
Is my fear based on reality or just a story I’m telling myself?
Most of the time, the worst-case scenario we imagine never happens. The fact is, people generally respect fundraisers who are bold enough to make an ask.
4. Understand and Honor Guilt and Shame
Guilt and shame are powerful emotions that can hold fundraisers back. Guilt is feeling bad about what you did (“I didn’t do enough”), while shame is feeling bad about who you are (“I’m not good enough”).
But here’s the truth: guilt and shame have a role in our lives. They keep us humble, but they shouldn’t hold us back. If you feel guilty after a donor meeting, ask yourself, “What can I learn from this?” Instead of letting negative emotions stop you, use them as fuel for growth.
5. Expand Your Ego-System
Your ego-system (not ecosystem) is how you see yourself. If something falls outside of your identity, you instinctively reject it.
For example, I see myself as a good singer. So if I mess up, it challenges my identity, which makes me uncomfortable. That’s why stepping outside your comfort zone is so hard—it forces you to redefine who you are.
Fundraisers who struggle with asking for money often see themselves as helpers, not sellers. But fundraising isn’t selling—it’s inviting people into something bigger than themselves. The sooner you expand your ego-system to include “I am someone who can confidently ask for and receive money”, the sooner fundraising becomes second nature.
6. Practice Gratitude for the Entire Experience
Every moment—whether it’s a big fundraising win or a total flop—has value.
As Tony Robbins says, “Life happens for you, not to you.” Even when things don’t go as planned, there’s always something to learn. Instead of beating yourself up over a missed opportunity, ask:
What did I gain from this experience?
How can I apply this lesson moving forward?
When we approach fundraising with gratitude, we become more resilient, optimistic, and open to growth.
Resources for Fundraisers
Taking Bold Action in Fundraising
At the end of the day, fundraising confidence isn’t about never feeling fear—it’s about taking action despite fear. Just like stepping onto a stage, picking up the phone, or making a big ask, confidence is built through doing.
If you want to become a stronger fundraiser:
- Take more risks
- Get comfortable with discomfort
- Give yourself permission to not be perfect
And above all—just go for it.
The next time you hesitate before making an ask, remember this: the courage you build today will make every future ask easier.
So, what’s your “karaoke moment” in fundraising? What’s the ask, call, or meeting you’ve been putting off? Take a deep breath, step up, and go for it.
You might just surprise yourself.