Family Holidays 2020: A Virtual Reality

The challenges of this holiday season present a unique opportunity to engage in conversations on values. Following these best practices can help ensure a constructive dialogue for your family.

2020 has been anything but ordinary, and this holiday season promises to be equally extraordinary. The pandemic, social inequity, political tensions and shelter-in-place orders have presented challenges for families everywhere. In many instances, these challenges have surfaced strong emotions, deepening family divides. And while research shows that the already stressful holidays are not the best time for intense family discussions, this year presents a unique opportunity for opening a dialogue and setting the groundwork for advancing family goals in 2021.

In the context of the powerful events of 2020, below we discuss several best practices for opening discussions with your family and clarifying the shared values that are critical to your wealth plan.

Make the Most of Virtual Settings

From social distancing to travel restrictions, COVID-19 has created numerous barriers to traditional holiday gatherings. While some may bristle at the prospect of replacing physical gatherings with virtual meet-ups, virtual settings can offer a number of advantages for holding meaningful family conversations. Keeping the following in mind as you plan can help facilitate productive discussions.

  • Schedule intentionally. Virtual meetings often work best with definitive start and end times, emphasizing quality of conversation over quantity. Generally, we suggest limiting discussions to under two hours in length. Ask family members to reflect on topics ahead of time and come prepared, and consider breaking complex subjects into subtopics and planning to discuss them across multiple sessions. This allows family members to digest concepts in-between sessions and return with a fresh perspective.

  • Emphasize equality. The potential for “jockeying for position” around the dining room table can leave some family members on the fringes, sending a message that some voices are less important than others. But whether your family is down the block or across the globe, everyone can have a seat at the head of a virtual table. Create a protocol that allows each family member an opportunity to offer input before moving on to the next topic. You may be surprised by the thoughtful dialogue from those less inclined to voice their opinions in traditional settings.

  • Set the stage for success. Scheduling physical gatherings with busy family members is never easy, particularly during the holidays. But virtual gatherings offer far greater accessibility. Additionally, virtual events meet everyone in the comfort of their own homes, where they are often most calm and present. Remember that while technologically savvy family members can seamlessly transition to a virtual meeting, you may need to work with those less familiar with virtual platforms ahead of time to ensure they are connected and ready to go.

  • Creatively foster connectivity. Our five senses trigger chemical reactions in our brain, creating emotions — both positive and negative. Shared history with our family is filled with past triggers that can work against us, unconsciously resurfacing with a familiar sight, smell or sound. Curate a bonding experience at your virtual gathering by sending a tangible gift ahead of time that stimulates positive triggers – grandma’s favorite cookies, a scented candle to remind family members of a favorite vacation spot or a bookmark with a treasured family motto.

Navigate Generational Divides

Diverse generational perspectives are not new, and the challenges of 2020 have intensified them. In late 2019, Chlöe Swarbrick, a member of the New Zealand Parliament, set the tone for the coming year in her response to heckling from an older colleague: “OK Boomer.” The exchange spread across the globe, underscoring a fragmented relationship between generations. Later in the year, high-profile members of the rising generation, such as Claudia Conway and Caroline Giuliani, strongly opposed their parents’ viewpoints in very public disputes.

All families have disagreements. Yet, heathy communication skills can enable families to transform diverse perspectives into common ground and develop a strong family culture inclusive of all opinions. This holiday season, look beyond stereotypes, and consider the varying generational attributes identified below as you discuss sensitive topics. Approach each discussion with an open mind, be inquisitive and listen carefully for points of commonality. By focusing on common ground, you may find that your family members’ core values are more similar than you expected, even if they are expressed differently.

  • Traditionalists grew up during the Great Depression and World War II. They respect authority, order and expertise. Also referred to as the Silent Generation, wealth often tops a long list of topics tagged inappropriate for discussion. Open dialogue around sensitive issues was not the norm.

  • Baby Boomers grew up in a thriving economy. They lived to work and were rewarded with financial success, reinforcing a strong work ethic instilled by traditionalist parents.

  • Generation X attitudes were formed by defining moments such as the Challenger shuttle disaster, the Enron scandal and the tech bubble of the 1990s. This generation is less trusting than previous generations, seeking to understand the details behind each decision.

  • Millennials grew up in the aftermath of 9/11, and the Great Recession hit when many were seeking their first jobs. This generation is skeptical of institutions and less trusting of authority figures. Millennials conduct independent research before making a decision and prefer to be part of the decision-making process.

Generalizations about generations

Ask the Right Questions

Initiating conversations on potentially sensitive issues can be daunting. But exploring the emotions surfaced by this year’s events can help your family find common ground on important topics that can be meaningfully integrated into your estate plan. (See Navigating Generational Divides.) Armed with generational empathy and virtual event tips, consider the questions below to start conversations on key topics with your family this holiday season.

  • Sustainable investing. Sustainable investing is a way to meet both an investment and social goal. Would this be a way to express our family values?

  • Philanthropy. Our family giving strategy has served us well in the past, but the world is changing quickly. Are there urgent local, national or global needs that align with our family values that we should consider supporting?

  • Family values. 2020 has given us a lot to think about. Have you considered our family goals and values in the context of this year’s events? Do you feel it is a good time to reassess?

  • Financial literacy. COVID-19 has created financial hardship for many, highlighting the importance of developing good personal finance habits. Have you identified your financial goals? Do you feel your spending, saving, investing and giving decisions are aligned with your goals?

This year has brought a host of unique challenges, in many instances resulting in greater tension between generations and family members. But by conscientiously creating environments where all family members feel comfortable expressing their opinions on key topics, you can foster conversations to drive your family’s priorities, and form the cornerstone of your wealth plan, for decades to come.

Multigenerational Families

Plan with Purpose

Build a plan that reflects your goals and values.

The Northern Trust Institute

Proven Advice for Moments that Matter


This information is not intended to be and should not be treated as legal, investment, accounting or tax advice and is for informational purposes only. Readers, including professionals, should under no circumstances rely upon this information as a substitute for their own research or for obtaining specific legal, accounting or tax advice from their own counsel. All information discussed herein is current only as of the date appearing in this material and is subject to change at any time without notice.

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