The Headless Donor of Sleepy Hollow

Jack was the third executive director the Sleepy Hollow Nonprofit had hired in as many years. No one was sure what fate befell them each year on All Hallow’s Eve. Louise liked to think that they’d simply left town and changed careers.

A Halloween short story dedicated to my friends and clients who serve on the boards of nonprofit organizations (or work for them).

Halloween dark scenery with naked trees, full moon and clouds“I’ve never much liked Halloween,” confessed Louise Van-Tassel, board chair of the Sleepy Hollow Nonprofit. “It’s not like Christmas and New Year’s, when people are filled with the spirit of giving or excited about making a new start. It’s more about stumbling around in the dark and having things frighten you.”

“And eating candy,” said Jack Crane, Sleepy Hollow’s new executive director. He pushed a bowl of candy corn across his cluttered desk to Louise. “Have some. It’ll help when you read our latest profit-and-loss statement.”

Louise sighed and picked a kernel of candy corn from the bowl, rationalizing that she had, after all, skipped the dressing on her salad at dinner. Now she wished she hadn’t. She needed some energy. Despite her best efforts, Sleepy Hollow’s board meetings tended to drag on into the night. She’d be lucky to be lugging her L.L. Bean tote bag full of files out to the dark parking lot by midnight.

“Which reminds me,” she said to Jack, who looked up from his laptop, “is there any way we could afford to install some more lighting in the parking lot?”

“Not if we’re going to stick with this new budget!”

“But over there by that big oak tree? It’s so dark and…creepy,” Louise protested. “Isn’t it a liability issue?”

“We’re insured.” Jack gave a dry laugh. “Are you another one of those board members who’s afraid you’ll run into the old Headless Donor in the parking lot? Board members have been trying to scare me with stories about him ever since I came to Sleepy Hollow. Louise, this organization will never get anywhere if it makes decisions based on the whims of some Headless Donor instead of on the actual needs of the people we’re chartered to serve.”

Louise shifted nervously in her chair and cleared her throat.

“Some of us have seen him, Jack.” She leaned over the desk and whispered. “He’s awfully big. And he carries that enormous…checkbook.”

Jack regarded her sternly over his dorky glasses. “Louise, you aren’t going to tell me about that old legend about the fundraising event he threw during Woodrow Wilson’s administration? When a board member he disagreed with was found on the front lawn, bludgeoned to death with copy of the proposed bylaws revisions the Headless Donor had opposed? For heavens sake, if this guy threw a party in 1914, he’d be…well, he’d be a ghost by now!”

Louise nodded unhappily and muttered, “Exactly.”

She could hear the voices of the board members out in the hall. People were arriving for the evening meeting. Jack had closed his laptop and picked up his papers. Louise followed him out of his office and into the boardroom, forcing a smile onto her face. She had a bad feeling about this Halloween meeting.

In fact, things got off to a bad start. Toni Brunt and another board member interrupted the agenda to enthuse about ideas for expanding Sleepy Hollow’s existing programs and starting new ones — including a program Toni dreamed up while she was talking.

“These are great ideas,” she said. “The board needs to act on them immediately!”

Jack’s plans for program cuts, staff cuts, and general fiscal austerity (which Toni and the other board member didn’t know about because they hadn’t read their pre-meeting materials) infuriated them. They were even angrier when they discovered that the majority of the board members, including the whole Finance Committee, enthusiastically supported Jack’s plans.

As the meeting progressed, the philosophical chasm between the two groups grew wider and deeper.  Louise wished she could just throw herself into it. The room heated up, and someone opened a window, letting in cold air along with the shrieks and screams of children making their Halloween rounds. Fueled by bowls of candy corn and the sugary supermarket cupcakes Toni had brought, the discussion raged into the night.

The board meeting ended just before midnight. Jack and the members of board majority shook hands and congratulated each other. Toni and the other dissatisfied board member gathered their papers and swept out.

As usual, Louise and Jack were the last to leave the building. To their surprise, Toni Brunt leaped out at them from behind a shrub. She struck a pose, her gray hair wild in the moonlight and her heavy black cloak flapping in the wind.

“You’ll be sorry,” Toni threatened. “Wait until the Headless Donor hears about this! I’ll tell him you’re ruining Sleepy Hollow!”

With a cackle, she swooped off into the night.

Jack just shook his head, and escorted Louise to her car at the far end of the parking lot. He assured her that the board minority would soon see reason about the finances.

“It’s simply a matter of standing our ground,” he told her. “Really, I can’t imagine why all of your previous executive directors couldn’t get a grip on this.”

As Louise drove off, she looked back and saw Jack, standing beneath the oak tree, waving. She also saw behind him a large, dark, headless figure, silhouetted by the moonlight. It was lumbering down the hill toward the parking lot.

“Oh, no, not again!” she wailed. Jack was the third executive director Sleepy Hollow had hired in as many years. No one was sure what fate befell them each year on All Hallow’s Eve. Louise liked to think that they’d simply left town and changed careers.

But she made a mental note of something to add to the next Executive Director’s job description:

“Must believe in ghosts.”