Maximizing Family Vacation

By Kim Frasca-Delaney, Senior VP, Client Advisor for Whittier Trust

In the fast-paced world of family office advisory, helping clients find just the right setting to have meaningful conversations about family finances can be a challenge. If you’re planning a family getaway to a relaxing tropical locale or an active ski trip with your loved ones, it might be tempting to consider bringing up serious financial topics. Clear communication within families, especially when it comes to wealth, is vital and there are risks and benefits to this strategy of turning a vacation into a family meeting. Read on for some things to consider.

Pros: Why a family vacation could be an ideal time to discuss wealth. Vacations create a relaxed and open atmosphere. It’s no secret that a getaway can create a unique environment where families can leave behind daily stresses and embrace a more relaxed mindset. Science backs this up: a 2022 study from the Journal of Frontiers in Sports and Active Living showed that vacations help people reduce stress in a quantifiable way for a wide variety of reasons. When all of the members of your family are relaxed and calm, it could be a good time to initiate a financial discussion and take advantage of this low-stress atmosphere.

Dedicated quality time brings loved ones together. Traveling as a family gives individuals segments of dedicated quality time you’re not likely to get within your daily routine at home. Whether it’s lounging on a beach, setting out on an adventure or exploring a new city together, these shared experiences can strengthen family bonds. Broaching financial topics during this quality time can leverage the emotional openness to make discussing wealth-related matters more comfortable.

Financial goals and family legacy come to life. Taking a curated or luxury trip can bring the benefits of stewarding wealth to life for future generations. While buying things or paying for once-in-a-lifetime experiences isn’t the only goal of wealth-building, those are compelling benefits. Vacations can also serve as a reminder of what truly matters: spending time with loved ones, pursuing passions and creating memories. Drawing a correlation to the freedom that comes from stewarding wealth effectively with positive experiences that the whole family enjoys can help give family members a clearer picture of the significance of financial planning in achieving their desired lifestyle.

Leading by example can educate the next generation. Family vacations offer an excellent opportunity to involve younger family members in discussions about finances. This approach not only helps prepare the next generation for their financial roles but also reinforces the importance of long-term family cohesion.

Cons: Reasons family vacation might not be an ideal time to discuss wealth. Disruption of quality time and relaxation Picture this: You have invited your family members on a lovely getaway—perhaps to a remote tropical island or a dude ranch out West.

They’re anticipating a week of low-key relaxation or exhilarating adventure activities. Then when you spring a serious discussion about family wealth on them, they might feel ambushed and emotionally unprepared for such a conversation. The strategy could backfire, and you might end up having an unproductive discussion and putting a damper on quality family time.

Finding the right setting and focus might be challenging. Depending on the vacation destination and your family’s travel style, it could be difficult to find the right environment to have a discussion about family wealth. If you’re in a bustling city where some family members are off to museums, others are shopping and still others are seeing shows, everyone’s schedules could be challenging to match up. Similarly, if you’re at a resort where activities from water sports to spa services fill up your loved ones’ days, squeezing in a thoughtful discussion session might feel like a distraction from the primary goal of rest and relaxation.

Emotions about finances may overshadow enjoyment. Wealth discussions can be fraught with strong feelings. Even in the most harmonious families, minor disagreements about the optimal course of action, what philanthropic causes to pursue or how to best administer future trusts can dampen the mood.

Additionally, if family members don’t know the extent of your wealth, introducing that information for the first time could be a shock. Bringing up financial topics during a vacation could exacerbate existing issues or create new conflicts, detracting from the vacation’s purpose of strengthening relationships.

Lack of preparation and ready resources could be unproductive. When family office advisors come to a family meeting, they’re prepared with comprehensive data, analysis and resources to facilitate informed discussions about family wealth. Vacation settings may lack access to these resources, making it difficult to provide accurate information. This could lead to misunderstandings or incomplete discussions, potentially causing more harm than good.

Every family is different. While discussing family finances on vacation can present unique opportunities and potential risks, it’s essential to take into consideration the personalities of your family members and how familiar they already are with the status of your wealth. Every family is unique because of their financial landscape and the unique personalities and concerns each family member brings to the table.

For Whittier Trust clients, we often recommend scheduling a dedicated family finance retreat to discuss family wealth in detail. This allows members to arrive mentally and emotionally prepared to engage in productive conversations in a focused environment. Whittier Trust advisors work with family leaders in advance to collect all the pertinent information. We can also help create structure around these discussions, as appropriate. If clients still feel strongly about initiating wealth talks during a vacation, it could be advantageous to prepare family members ahead of time by saying something like, “This trip will be mostly fun, but we want to build in an hour or so to talk about some family business.” That way, no one feels caught off guard and the group can focus on what’s most important: spending time together.