Scott Jessup ’77, ’80MBA, opens his laptop and scans the dozens of emails waiting in his inbox. One comes from a woman he’s never met. After describing her struggles, she asks the question that’s been weighing on her most: Would my dad be proud of me?
This is not the first such message Jessup has received, so he knows what to do. With so many similar letters awaiting him, he knows his reply is overdue, and he apologizes for the delay. He restates what the letter-writer shared, so she knows he truly heard her. Then he does his best to answer.
He prints out his typed letter — he says his handwriting is so bad that even he can’t read it. Then he sketches his goldendoodle, Finn, in the margin. Above the dog’s head, he draws a thought bubble with the recipient’s name inside it to make his letter feel even more personal.
“You need to give them support and belief, even if it only lasts for the two minutes that they read the letter,” Jessup says of his responses to the people who reach out to him in this way. “It might be short term; I’m not changing lives. But if they read my letter and feel better for a little bit, that’s a win.”
This past year, Jessup has written hundreds of letters to strangers through the Dad Letter Project, a nonprofit organization that connects volunteer fathers with people longing for understanding or compassion. Many are grieving a parent they’ve lost — or never had.
Long before he started volunteering with the project in January 2026, Jessup felt that writing was his most natural way of connecting with people. Every December, he writes a family Christmas letter, typically forgoing a rehash of major accomplishments in favor of stories about small victories and everyday mishaps: moving three times in one year; broken bones; the arrival of a new puppy (a “galvanized garbage disposal wrapped in fur”); a report that their two teenage sons “won’t let us speak to them in public anymore.”
“I do take some artistic license,” Jessup says with a smile. “I see humor in almost anything that’s not fatal.”
Even when his teenage children begged him to stop sending the letters, he refused. “They were threatening to leave,” he jokes. “That was the most fun I had every year.”
Writing became his favorite tool for professional communication as well.
After a career helping veteran-owned businesses navigate acquisitions, Jessup joined Notre Dame’s development office in 2004. He was decades older than most of his coworkers and liked trying to help them in their new roles. He also enjoyed creating connections with donors, but he was not one for phone calls. Instead, he preferred to write.
“I’m not a good phone guy,” he says. “I would write way-too-long emails, but that’s how I developed relationships.”
The deeper reason he was drawn to the Dad Letter Project comes from his own family. When Jessup’s mother was 9, her mother and father died within six months of each other. She entered the foster care system and remained there until adulthood.
“It was unbelievable that she was a functional adult and a great mother,” Jessup says. “But she was not demon free.”
He often imagines what a simple letter might have meant to her during her childhood.
“I thought, if somebody along the way had written her a letter just saying, ‘You’re doing great. It’s hard. This isn’t fair, but you’re getting up, you’re going to school, you’re working. . . .’ I like to think about what that would have meant to her.”
When Jessup retired from Notre Dame in 2019, he made a short list of what he might like to do next. The work needed to be meaningful and flexible, make use of his strengths and involve good people. He spent some time advising nonprofits and mission-driven startups. Then, in 2025, his youngest son, John, introduced him to what felt like the perfect fit: The Dad Letter Project.
“It was the culmination of everything in my life up to that point,” he says. “I’m a dad, a husband, a brother, a friend — and I’m a letter-writer.”
John Jessup had met project founders Rosie Paulik and Mara Timmeney at the summer camp they had all attended as children, and their friend Kit, John’s cousin, had mentioned that her Uncle Scott served on the camp’s board.
Jessup applied, completed background checks and interviews, submitted writing samples and was accepted as one of the volunteer dads in January. At first, he committed to writing three letters a week. That pace quickly changed.
“Honest to God, they were so heartbreaking,” he says. “They were so deeply moving that I started writing, and all of a sudden I’m like, ‘Oh, I’ve got to do two or three daily.’”
One letter in particular stayed with him: a woman searching for an example of the kind of man she hoped her son would become. Her own father had left, her son’s father was nowhere to be found, and her boss, she said, was “a jerk.” I have never seen a good man, she wrote. How do I teach my son to be a good man?
Jessup has made good on his promise to write more letters. But as the organization grows, so does the need. It started with a social media post Paulik wrote in July 2025 about her own father’s remarkable letter-writing habits and how much they mean to her. She asked, “Would you want a letter from my dad?”
The post went viral. As of this writing, more than 10,000 request letters have arrived from over 50 countries; 95 percent come from women. Roughly 30 volunteer dads have been trying to keep up, while the effort operates without any full-time staff. Whenever the project appears in the news or on social media, another wave of requests follows.
“We were kind of stuck in neutral,” Jessup recalls of his first weeks. “It’s amazing, but it couldn’t scale, and sooner or later it was going to fall under its own weight.”
He soon recognized that answering letters was only part of the work and wanted to help build the organization. His first step was helping establish it formally as an Ohio-based nonprofit.
Today, as the project’s board treasurer, Jessup helps raise money, advises Paulik and Timmeney, participates in weekly planning meetings, interviews new hires and works to secure the project’s long-term future. It’s familiar work, hearkening back to his years supporting entrepreneurs and mentoring young colleagues.
The letters remain at the center of it all. In his quiet home office in South Bend, Jessup opens another email. Somewhere, someone is wondering whether they’re enough, whether they’ve made their father proud, whether anyone believes in them.
He can’t answer every question with certainty. But one letter at a time, Scott Jessup makes sure no one asks those questions by themselves.
Michelle Cuneo is an associate editor of this magazine.