Five Conversation Starters for Your Family’s Thanksgiving ‘Cousin Walk’

Picture this: At Thanksgiving gatherings across the country, a quiet ritual unfolds. Younger family members grab their coats, exchange knowing glances, and slip out the door for what’s become known as the “cousin walk.”

This week the Wall Street Journal put a name to this longstanding multigenerational tradition. The term encompasses everything from literal walks around the neighborhood to dog-walking, trail hiking, or playing disc golf – any activity that creates space for generation-specific connection across branches of the family tree.

From Counterculture to Mainstream

I became aware of cousin walks in the early 1970s at our large family Thanksgiving gatherings, which often hosted 40, 50, or more relatives. I was just 10 or 12 years old when my older cousins began disappearing during the festivities. I had no idea where they went, but I remember them returning in ebullient moods to play the newest records and laugh at comedy albums that were decidedly different from the Bill Cosby and Bob Newhart my parents enjoyed. I was catching my first glimpse of the counterculture.

What was once counterculture has gone mainstream. The Journal notes that the cousin walk – which also goes by “Thanksgiving walk” and “pre-dinner safety meeting” – is significant enough to drive major sales on what’s now called “Green Wednesday,” a cannabis-buying phenomenon the day before Thanksgiving that dispensaries report as often their second-biggest sales day after April 20th.

Why Cousin Connections Matter to Family Enterprise

Not all cousin walkers are seeking altered states. Many simply treasure the rare opportunity to connect with peers who understand the unique experience of growing up in their particular family system. For business-owning families, these relational bonds aren’t just nice to have – they’re foundational to long-term success.

Dennis Jaffe observes that young family members in generative families must learn skills beyond their personal careers: “Because their family is linked by trusts and shared financial entities, they must learn skills to oversee and manage these assets and learn how to work together in harmony with siblings, cousins, and spouses.” (Borrowed from Your Grandchildren: The Evolution of 100-Year Family Enterprises, Wiley: 2020, p. 288) Such coordination and harmony grows from a foundation of trusting, respectful relationships built over time – often during informal moments exactly like cousin walks.

While this piece celebrates family connection, I’d be remiss not to acknowledge that substance use can become a serious problem in some families, including business-owning ones. It became an issue for several of my cousins. If your family is struggling with addiction, help is available. Organizations like Burning Tree Ranch specialize in supporting chronic relapsers toward permanent recovery.

Five Questions for Your Next Cousin Walk

Whether your cousins take a literal walk tomorrow or simply find a quiet moment together this holiday season, here are five conversation starters designed to strengthen understanding and build the relationships that will carry your family enterprise forward. They’re intentionally non-threatening—there are no right or wrong answers, just opportunities for genuine connection.

  1. What is one thing you enjoy about growing up in a business-owning family?
  2. What is one thing about growing up in a business-owning family that is or has been a challenge for you?
  3. What would you say your family is known for? What would you like your generation to be known for?
  4. What is one thing about the family or a family business that you would like to learn more about?
  5. What’s one thing about your family or family enterprise that you feel should be preserved for future generations? Do you see a need for innovation? If so, in what sense?

Grateful Hearts

Wherever you are on Thanksgiving Day, and whomever you dine or walk with, I hope you truly appreciate your blessings. I recall a beautiful pastoral prayer from many years ago that ended with this petition: “O Lord, you have given us so much; give us one thing more: grateful hearts.”

And I would add, the wisdom to nurture the relationships that will carry our family enterprises forward.

Happy Thanksgiving!

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MEET THE AUTHOR

Fred Oaks

Principal Consultant at Family Business Facilitators

Fred Oaks, Principal Consultant at Family Business Facilitators, is a seasoned professional facilitator specializing in multigenerational family businesses. He has been consulting since 2003 and spent 17 years as a program officer in a family foundation. His work as a senior pastor also informs his ability to maintain confidentiality and connect in meaningful ways. His approach fosters faithful stewardship and generative family dynamics, ensuring long-term success.

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