The holidays, so often sold as the season of togetherness, can be among the most complicated days of the year, especially for those trying to stitch together custody arrangements, crowded schedules, family traditions, and long stretches of highway between loved ones. And yet, as one Boston woman reflects with joy, it doesn’t have to be so hard.
Jess Wilson points to her 85-year-old father, a man who happily abandoned the tyranny of the calendar decades ago.
Wilson, a mother of two adult daughters, was 11 years old when her parents divorced. Because she lived with her father, she said, in an interview with TODAY.com, it became especially important to her mother that she be present for all the major holidays. “No big deal,” her dad, a middle school principal for 45-years, told her.
Drawing on instinct for calm over conflict, he proposed a simple solution: holidays didn’t have to happen on their designated dates.
“He’s always said, ‘We can create the magic whenever we want,’” Wilson tells TODAY. “The magic of Christmas morning is made by the family. It doesn’t matter if it’s the 25th on the calendar.”
In the Wilson family, the traditional date has long been treated less as a rulebook and more as a suggestion. Thanksgiving was often celebrated on a different day, and birthdays followed the same logic. Wilson's birthday falls in August, but for her father, waiting has never been part of the tradition. He typically gives her a gift in February, months early, unable to hold back once he finds something he is excited to give.
“He can’t wait,” she says, laughing.
Last year, Wilson shared her father’s approach to holidays on her Facebook page, Diary of a Mom, and again this year, where it quickly spread across the platform.
“My dad has always insisted that I spend all of the major holidays with him. The qualifier was that they could happen whenever it was convenient for me, and later, as my family grew, for all of us,” Wilson wrote. “Christmas on Jan 2nd? Sure, why not? It’s still Christmas if you say it is. No guilt. No competition. No one left out."
The post included a photo of him sliding a slice of pie across the breakfast table, a yearly ritual the morning after they celebrate Thanksgiving.
“Over the years it’s been one of his greatest gifts to us,” and one Wilson said she is determined to carry forward with her own kids.
The comments filled with stories from adults raised in divorced homes and couples juggling in-laws and competing expectations. Many wrote that the post gave them permission to let go of perfection and instead choose peace and presence over strict timing.
While chatting with TODAY, Wilson couldn’t thank her father enough for “taking the pressure off” and for making the holidays what they are meant to be, rather than something to endure.
“My dad is amazing. He is so supportive and generous in spirit, and he just wants the world to be a better place,” she says.
The instinct extends beyond his family and into his every day life. At a local park near his home in New York, neighbors and their dogs, regularly gather around him in what regulars have nicknamed the “Breakfast Club.”
Each morning, he arrives with a bag of chicken jerky, drawing a small crowd of wagging tails and familiar faces. When he learned that one pup was allergic to chicken, Wilson said, he started bringing duck jerky just for that dog, a small detail that, to those who know him, says everything.
