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Some people love the holidays because it’s a reunion of family. Some love the endless stream of football games. Most people love the food, especially those dishes that are cherished family recipes that only come out on the holidays. At Pendleton Square Trust Company, our favorite part of the holidays is the stories.

This holiday season, we encourage you to make time for the stories. The quality time together and the holiday meals with family and friends are a perfect venue for storytelling.  For families, stories are a sort of lifeblood. They strengthen the ties between siblings and between generations – even stories of people who have passed away – and give younger generations a strong feeling of belonging.

In short, stories make families stronger. And when the same stories are told year after year, it’s like adding another seam to the same pieces of fabric. Your connection is made stronger.

As you plan your holiday dinners this year, we suggest using two basic kinds of prompts to stimulate storytelling. The first is the kind that elicits details and specific memories. The second kind evokes opinions, advice or declarations.


Some of the people around your table will flock to this kind of question, and children make fabulous – and irresistible – interviewers.

  • “Who was your best friend when you were my age?”
  • “When did you first meet Grandma?”
  • “What did the inside of your house look like?”
  • “What was your first job?”

This type of question allows the answering party to reminisce, return emotionally to another time and paint a picture that may stun listeners with how different it was then versus today. The answers are a treat for both the responder and audience, who get to walk mentally with the memory bearer through his or her life.


This other kind of question stimulates imagination and opinion.

  • “What personal values do you admire?”
  • “What kind of holiday traditions are your favorites?”
  • “What is the single piece of advice you would offer the children here?”
  • “Who is the most important person of the 20th century?”

These questions appeal to people who have strong opinions and like passing on their acquired wisdom.  A great question connects wise elders with their (not yet so wise) grandchildren.

Telling stories is critical to family engagement. The more they are told, the more they are remembered; and the more they are remembered, the more they get passed down and become part of the family culture. However your holiday table stories unfold this year, we strongly recommend documenting them. Smart phones are well equipped for recording audio on the spur of the moment, but transcribing a story in handwriting can result in a priceless family heirloom that documents the story and also the handwriting of the documenter.

We are impressed by, an award-winning web-based platform for storytelling, documenting and sharing. Pass It Down makes storytelling simple by providing hundreds of questions, created by leading biographers and oral historians, to help guide your family though the process of capturing memories. Chris Cummings, Founder & CEO, established Pass It Down to help families capture their stories after his mother was diagnosed with dementia at the age of 48.

The Pendleton Square family wishes you a memorable holiday season filled with good food and great family stories!

Betsy Brown

Betsy Brown, CEO of Pendleton Square Trust Company, serves families and advisors to deliver trust and estate services. She is passionate about developing thoughtful legacy plans and educating beneficiaries.

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