Nonprofit Scary Stories to Tell in the Dark (to Minimize Electricity-Based Overhead) 2026
Hi everyone. Reminder: This Wednesday October 21st at 10am Pacific Time, please join me and fellow rabble-rouser Aparna Rae for a fun and informal conversation where we bust some of the myths about nonprofit and philanthropy. It’s free, and will be auto-captioned. Register here.
Halloween is around the corner, which means it's time for the annual scary stories set in our sector. Below are some spooky tales written to give you shivers. Read them by yourself in the dark if you dare.
FOUNDER'S SYNDROME 2.0
There was a nonprofit whose founder and board chair had been there for 32 years. And while the organization was moderately successful, the ED felt constantly undermined, and the staff yearned for new leadership. But the founder was influential and held a lot of the funding relationships.
One board meeting, she decided to call in through video. Gradually, she stopped showing up in person for anything. On video, her voice was a bit stilted and unnatural, and her stares were vacant, soul-less, not unlike that of a billionaire.
Months went by. One day, a board member was in the founder’s neighborhood and decided to stop by. When he knocked, the founder’s son answered. On the TV was the founder, waving hello. “Mother passed away last year,” he said, “she wanted to keep her death a secret. She said she still had a lot to do and requested we us AI to recreate her. Mother says she’s been having a great time on your board.”
The board member left as quickly as he could and called for an emergency board meeting on zoom. They had no protocol in the bylaws for removing an AI board member. But also, she was still maintaining their funding relationships, so was it really all that bad? They decided to keep her on the board and not tell the staff or anyone else.
Suddenly the founder entered the meeting. "I knew you would all make the right decision and I wouldn't have to write and publish a hit piece calling you all terrorists and sending it to the IRS," she said. "Just kidding! Now, who's ready to talk about the theme for our gala?"
THE INFINITY SCARF
The nonprofit had been searching for a new executive director for a while. Neither of the two they had hired previously lasted longer than a year before quitting. Then a new candidate appeared. He didn’t have much experience in the sector, but the hiring committee thought many of his skills could transfer.
During the first interview, he showed up on time, dressed in a suit and tie. Tightly wrapped around his neck was a blood red infinity scarf. Though the room was warm, he never took off the scarf. During the second and third interview and even on a day-long program tour, the scarf never left his neck.
At the end, he was hired. On the first day, at the all-staff meeting, he introduced himself, still wearing the crimson cloth. “Feel free to ask me anything,” he concluded to the excited but anxious room.
Everyone was silent. Then an intern raised his hand. “Can you tell us why you always wear that red scarf?”
The man’s face went pale. Then it morphed into a twisted smile, and he slowly started removing the scarf. He held it in his hand and scanned the room. Everyone held their breath.
“Sell me this scarf,” said the new ED. The staff looked around at one another, confused.
“Sell me this scarf,” he repeated, “If we’re going to be successful, this nonprofit needs to run like a for-profit. And that means all of you must develop and improve your sales skills. So everyone will take turns today standing here in front of the room, selling me this scarf.
A chill ran up everyone’s spine, as if a malevolent invisible presence was in the room with them.
“Pretend you’re on Shark Tank!”
DAF
It was a cold a dark evening. The trustees of the foundation were having the last of their quarterly meetings for the year. "How are we doing? Did we meet the annual 5% payout required by law?" asked the board chair, a stern-looking octogenarian.
The CEO, a man in his late 40s, answered, "I'm afraid not. Even with us giving everyone on our staff a 25% raise and hiring Boyz II Men for our annual retreat, we barely managed to crack 3%."
A young woman, the only non-family trustee, said, "How about we give out more funds to our grantees, especially those working to save democracy? The midterms are coming, and it would make a significant difference..."
Her voice trailed off as the other trustees' eyes glazed over and they stared into space, as was the pattern whenever she spoke. A silence fell upon the room.
Finally, a man coughed. Light returned to everyone's eyes. They seemed excited to hear his thoughts. "Technically," he said, smirking, "any money to we set aside in a Donor-Advised Fund counts towards the 5%. And DAFs have zero laws requiring us to disburse to nonprofits. So I move we allocate enough funding to a DAF to satisfy the 5% payout rule."
Someone seconded. The motion was passed by all but one vote. Some say that on nights like these, if you listen carefully, you can hear the wailing of a thousand nonprofit leaders and democracy advocates.
OPTIONAL
“Just one last thing,” said her supervisor at the end of the onboarding process, beaming a wide smile, sliding over a piece of paper. She had filled out all the other paperwork. Nothing unusual, just tax forms, emergency contacts, bank accounts for direct deposit, and even a “get-to-know-you” survey that asked for her favorite snacks.
“This is the employee giving campaign form. It’s completely optional, of course.”
She looked at the form. Below the contact information there were two checkboxes. One said, “I would like to make a monthly contribution through automatic deduction of my biweekly paycheck in the amount of $-—."
Next to it was another checkbox that said, “I would NOT like to make a monthly contribution.”
She moved to select the second box. Before she could mark it, the supervisor, who was still smiling, said, “Most people here do $50 a month. All the senior staff do $250 each. Whatever is personally significant for you. No pressure."
And again, she moved her hand to the second checkbox. As she was about to check it, the supervisor said, "We do try to get 100% employee giving. But like I said, it’s completely optional.”
Outside, the skies suddenly darkened and rain started falling, striking the windowpanes. The supervisor stood still, her visage frozen in that wide, unrelenting grimace.
THE INFINITY SCARF, PART 2
It had been a year since the new ED came in. Days after the Shark Tank exercise where he made all 18 staff members go up one by one to make a pitch selling the scarf, he brought in a marketing colleague from a Fortune 500 company for an AMA (Ask Me Anything). He assigned memoirs written by corporation CEOs. During one team meeting, he printed out copies of a list of corporate jargon and handed them out to everyone. He tried to do similar things with the board.
One day, he announced the decision to stop applying for grants and instead focus on earned revenues, and he pulled the board and staff into a two-day retreat to brainstorm potential income-generating activities. He proposed an app-based service homeless people could subscribe to that would help them find resources.
After that retreat, he was never seen again. Some say he found a better job and just left. Others say the board fired him because his antics ended up costing the organization revenues and staff.
And yet others whisper rumors of a small group of staff who ambushed him, soaked his infinity scarf in leftover gala wine, and slapped him with it until he agreed to leave town and never apply for a nonprofit position again.
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Related posts:
Scary Nonprofit Stories to Tell in the Dark 2025
Scary Nonprofit Stories for Halloween 2024
Scary Nonprofit Stories to Tell in the Dark 2021
Scary Nonprofit Stories for Halloween 2020
7 Nonprofit Scary Stories to Tell in the Dark
More Nonprofit Scary Stories to Tell in the Dark
3 Nonprofit Ghost Stories to Send Chills Up Your Spine
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