Courage Over Confidence: The Real Secret to Fundraising That Works

If you’ve ever said,
“I know I need to do outreach… but I don’t feel confident yet,”
This is for you.

Here’s the truth most nonprofit leaders don’t hear enough:

You don’t need confidence to fundraise.
You need courage.

Confidence is what shows up after you’ve done the thing a hundred times.
Courage is what lets you do it the first time.

And the second.
And the awkward, sweaty-palmed, “I hope this works” third time.

Stop Waiting for Confidence

Confidence doesn’t come first.
Practice does.

Think about riding a bike.
The first few times? Wobbly. Unsteady. Not cute.
The hundredth time? You don’t even think about it.

Fundraising works the same way.

If you wait to feel confident before you reach out, follow up, or ask, you’ll stay stuck in draft mode forever—editing emails that never get sent, planning campaigns that never launch, and telling yourself you’ll start “when you’re ready.”

You’re already ready.
You just need courage.

Imperfect Asks Raise Real Money

Most people say, “My asking feels awkward.”

Good.
That means you’re doing it.

There is no single “right” way to ask.
There is only your way—honest, human, sometimes clunky, always real.

Perfection doesn’t raise money.
Action does.

Waiting to sound better, smarter, or more polished only delays the moment when you actually get better.

Imperfect outreach:

  • Builds skill

  • Builds confidence

  • Builds funding

Silence builds nothing.

Why We Avoid Outreach

Let’s be honest about why outreach drops to the bottom of the list.

Not because it’s unimportant.
But because it’s the riskiest.

You can’t get rejected by:

  • Drafting an email you never send

  • Editing a blog post for the fifth time

  • Planning a campaign that never launches

Rejection only happens when you take action.

So we hide in “productive” tasks that feel safe—and quietly avoid the one thing that actually brings in money.

Once you see that pattern, you can interrupt it.

Avoidance isn’t laziness.
It’s fear wearing a productivity costume.

Follow-Up Is Where Funding Lives

Another common pattern:

Great first meeting.
Strong connection.
Then… nothing.

Why?

Because the emotional high of the meeting fades, and the story starts:
“They would’ve donated if they really wanted to.”
“They would’ve followed up.”
“They probably changed their mind.”

So you don’t follow up—and momentum dies.

Follow-up isn’t annoying.
It’s leadership.

Most donors are busy, not disinterested.
They’re waiting for clarity, timing, or one more nudge.

Your job is not to mind-read.
Your job is to lead.

Kids Know How to Handle “No” Better Than Adults

Watch a kid play sports.

They lose.
They cry.
They get a snack.
They move on.

They feel the feeling—and let it pass.

Adults?
We turn one “no” into a story about our worth, our mission, and our future.

Rejection doesn’t mean:

  • Your cause isn’t valuable

  • You’re bad at fundraising

  • You should stop asking

It means:
That person wasn’t a yes today.

Feel it.
Move through it.
Keep going.

The $10,000 Question

Imagine this:

If you had to raise $10,000 this week—or your nonprofit shut down—what would you do?

You wouldn’t:

  • Overthink it

  • Perfect it

  • Wait for confidence

You’d call people.
Email people.
Activate your network.
Move fast.

And it would feel:

  • Heavy

  • Stressful

  • Uncomfortable

But also: worth it.

So the real question isn’t,
“Can I handle discomfort?”
It’s,
“Is my mission worth a little discomfort?”

If your answer is yes, then courage—not comfort—has to lead.

Get Comfortable Being Uncomfortable

You already do uncomfortable things:

  • Doctor visits

  • Dentist appointments

  • Hard conversations

  • Big decisions

You don’t do them because they feel good.
You do them because the outcome matters.

Fundraising is the same.

You don’t have to love it.
You just have to lead through it.

Think–Feel–Do: The Real Cycle

Sometimes we think first, then feel, then act.
Sometimes we feel first—tight chest, sweaty palms, fast heartbeat—and then our brain jumps in with stories.

That’s when you pause and ask:

  • What am I actually thinking right now?

  • What story am I telling about this ask?

  • Is that story helping or hurting me?

You don’t calm fear by pretending it’s not there.
You calm it by understanding it—and choosing action anyway.

Courage Builds Confidence

Every outreach you send.
Every follow-up you make.
Every imperfect ask you try.

That’s how confidence is built.

Not in theory.
Not in planning.
Not in waiting.

But in doing.

Your mission doesn’t need a perfect fundraiser.
It needs a courageous one.

Christina Edwards