The biggest battle in fundraising is the battle in your head.
A few weeks ago, I asked someone to give.
It was a significant gift, and it rattled me.
I didn’t sleep well the night before. I kept rehearsing my side of the conversation over and over again in my head. I was stuck in a loop.
Why was I so nervous?
Several reasons.
1. The portfolio of individual relationships I steward (less than 40) is relatively small.
That means each relationship has an outsized impact on the overall total I’m responsible for raising.
A few ‘no’s’ here and there in a portfolio of 150+ is manageable.
A few ‘no’s’ in a portfolio of 40 feels like a big deal.
2. It had been a while since I’d made an ask.
I changed roles in February and have spent the last several months learning my team, meeting our donors, and thinking through strategy.
This was the first couple I’d personally invited to give since starting the new role.
Honestly, I felt a little rusty.
3. The ask was significant.
Not only do I have a relatively small portfolio of relationships that I manage, and not only had it been a while since I’d asked someone to give, but this particular gift was likely the largest I’d ask for this year.
It was also going to be the largest gift anyone from our organization had ever asked this couple to give.
No big deal, right?
4. I didn’t feel like I’d done enough relational work to earn the right to ask.
This is easy to name as a lie after the fact, but in the moment, it felt pretty real.
Even though I’d spent time with this couple … even though we had talked about why they give … even though I had confirmed their interest in giving again … even though I asked their permission to invite them to give … I still felt like I could have done more.
If you want to raise money, you have to get good at recognizing this head game for what it is.
My friend Mike Crandall calls it head trash, and even though it’s all a mind game, it can wreck you in fundraising if you’re not careful.
There is no such thing as the perfect ask. There is no perfect time to ask.
Are there bad asks? Yes. Are there bad times to ask? Yes.
But in fundraising, as in most of life, perfect is often the enemy of good.
What did I do?
I asked anyway.
What did they say?
Email me and I’ll tell you. Honestly, their answer doesn’t matter.
What matters is that I pushed through and asked anyway.
Fundraising is uncomfortable. It’s uncertain. And you’ll always feel a little unprepared.
There will always be moreyou could have done to earn the right to ask.
These feelings are normal and everyone else out there raising money has felt the same way at some point.
What can you do?
Ask anyway.
Scared? Ask anyway.
Doubting yourself? Ask anyway.
Not ready? Ask anyway.
Every time you do, you’re building resilience, developing your skills, and pushing back against the head trash holding you back. Who knows? You might even secure a gift.
The biggest challenges in fundraising rarely come from anywhere “out there” – reluctant donors, economic downturns, or competing causes.
The biggest obstacles in fundraising are usually the ones living right between your ears.
