Spooky Scary Halloween Edition
Can I tell you a scary story?
It’s about something that haunts every fundraiser I know. Something that keeps us up at night, staring at our phones, refreshing our email one more time before bed.
It’s about silence.
The kind that makes you question everything you thought you knew about a relationship. The kind that whispers, “Maybe they’re avoiding you” until you can’t hear anything else.
This is a story about that kind of silence.
I’d been trying to reach a couple since May about a gift.
I’d sent SO MANY emails. Texted. Called. Left voicemails.
Cue the ominous music.
And then. All of a sudden. Out of nowhere…
JUMP SCARE?!?!?!
Nope. The opposite, actually.
The couple finally responded this week.
After five months of me texting, calling, and emailing like some kind of fundraising stalker, they sent one message: “No need for a call. We’ll be sending a year-end gift.”
I suspect it’ll be six figures.
I should probably be embarrassed about how many times I reached out.
I’m not. Here’s why…
This couple gives away millions. To over 70 organizations. While running a business and raising a family.
They’re not avoiding me. They’re triaging a life that would break most of us.
And somewhere in that chaos, buried under 47 other urgent things, was my message. Waiting. Just… waiting for the right Tuesday when they had five minutes and remembered, “Oh right, we wanted to do that.”
Most fundraisers would’ve stopped at attempt three. Maybe five if they were feeling brave.
Maybe you can relate? Maybe you know the cold dread when you check your inbox for the fifteenth time and there’s still nothing? Maybe you know that sinking sensation when another voicemail goes unreturned or that 2 a.m. spiral when you’re convinced you’ve somehow scared them away forever and you draft an apology email you’ll thankfully never send?
It’s the fundraising version of a horror movie. Except instead of being chased by a masked villain, you’re being haunted by unanswered emails and one terrifying question: “Did I do something wrong?”
For the last five months, I’ve lived on the verge of that spiral.
Was I being annoying? Should I give up? Had I completely misread the relationship? There were moments (usually at night, always when I was tired) when I thought maybe I should take the hint. Maybe this was a lost cause. Maybe I was being delusional.
But something told me to keep trying.
And so I did because I refused to confuse “bad timing” with “bad relationship.”
Every few weeks: Thinking of you. Here when you’re ready. That’s it. No passive-aggressive “per my last email.” No guilt. Just consistent presence.
My friend Risa Forrester calls this being “appropriately assertive,” which sounds way better than what it felt like… throwing messages into a void and hoping one eventually lands.
Here’s how this nightmare usually unfolds for most fundraisers.
You send an email. No response.
You try again a week later. Nothing.
You leave a voicemail. Radio silence.
And that’s when the voices start whispering in the darkness.
“They must be too busy.”
“I don’t want to bother them.”
“Maybe they’re just not interested.”
“I’ve probably annoyed them by now.”
“They’re avoiding me.”
And just like that, you stop trying.
Roll credits. The end.
Those voices? They’re coming from the monster inside your own head not the donors who haven’t responded.
The real monsters are the fears lurking in your own head that convince you to abandon ship before the relationship actually dies.
And so here’s the truth every fundraiser needs tattooed backward on their forehead so they see it in the mirror each morning:
Donor silence is almost never about you.
People aren’t ignoring you because your last appeal sucked. They’re not dodging your calls because they regret giving. They’re not haunting you with radio silence because they think you’re incompetent.
They’re just humans with 847 things happening, and your thing is #386.
The actual scary thing?
The voice in your head that says, “stop trying, you’re being annoying.” That’s what kills the relationship. Not your persistence.
Because when you stop reaching out to “be polite,” you’re not protecting anything. You’re disappearing. And a disappeared fundraiser might as well be dead.
The scariest thing in fundraising isn’t getting ghosted.
It’s mistaking “not now” for “not ever” and walking away from a relationship that just needed more time.
It’s giving up on someone who was always planning to say yes… they just needed a few more months to get there.
So how does this story end?
Not with a scream. Not with regret. Not with a relationship that faded into the fog.
This story ends with a text message response after five months. It ends with a year-end gift. It ends with the realization that persistence, not fear, writes the better ending.
This Halloween, don’t let the voices win.
Be persistent instead.
Be so persistent it feels uncomfortable.
Okay… perhaps not that uncomfortable.
Don’t be pushy or rude. Don’t be an aggressive pest.
Again… not like that.
Nope. Just keep showing up. Keep reaching out. Keep being appropriately assertive.
What relationship have you given up on that might just need a bit more patience and persistence?
Because sometimes the donors who scare you most with their silence are often one message away from saying yes.
They just needed twelve more tries to get there.
Happy Halloween Friends!
-Michael
