How to Discuss Wealth and Philanthropy With Your Family at Year-End

How to Discuss Wealth and Philanthropy with Your Family at Year-End

For many successful, busy women, the holiday season represents more than festive gatherings and traditions. It’s one of the rare times when families pause, reconnect, and come together around a shared table. This unique season offers something else too: a powerful opportunity to start meaningful conversations about wealth, values, and the legacy you hope to build.

While money conversations can feel uncomfortable or even overwhelming, they don’t have to be heavy or formal. In fact, some of the most impactful discussions about wealth and giving begin in simple, genuine moments around the holidays. 

As the year comes to a close and many families consider year-end tax planning, this moment becomes especially valuable. Charitable giving decisions, beneficiary updates, donor-advised fund contributions, and strategic gifting can spark rich dialogue about purpose and priorities. And when we invite younger generations into these conversations, we’re not just transferring wealth. We’re passing forward wisdom, values, and a mindset about what money can do.

Here’s how to begin these meaningful conversations with confidence, clarity, and connection this holiday season.

Why These Conversations Matter - Now More Than Ever!

Women often carry a central role in shaping family culture and communication. Research shows that women are the primary drivers of philanthropic decisions and are more likely than men to frame wealth in terms of meaning, impact, and relationships rather than accumulation alone. Many women also serve as emotional anchors and organizers within their families—making them uniquely positioned to guide conversations about financial purpose.

At the same time, more wealth than ever is transitioning between generations. Over the next two decades, an estimated $84 trillion will pass from older generations to their heirs, and women will increasingly guide how that wealth is stewarded. If conversations don’t happen early, families may experience confusion, conflict, or missed opportunities.

When we talk openly about giving, goals, and values, we:

• Strengthen trust and unity across generations
• Prepare children and grandchildren to manage wealth responsibly
• Decrease anxiety or uncertainty about the future
• Build shared purpose and stronger relationships
• Ensure that family wealth supports what matters most

The holidays are one of the few times when these conversations can happen naturally and with warmth rather than urgency.

Starting the Conversation: Gentle and Accessible Ways to Begin

Conversations about money don’t need to sound like legal briefings or boardroom agendas. They are, at their heart, conversations about family. It’s an opportunity to share a part of who you are, what you stand for, and what kind of legacy you hope to leave behind.

Here are approachable ways to begin:

1. Start with values, not numbers

You might begin with a question such as:

• “What causes or organizations matter most to you this year?”
• “If you could solve one problem in the world, what would it be?”
• “What do you think it means to ‘use money well’?”

Most people feel safe and engaged when the focus is on purpose rather than dollars.

2. Share your own story

Explain why giving is meaningful to you:

• Perhaps generosity was modeled by your parents or grandparents.
• Maybe a life experience shaped what you care about.
• Or you have learned that giving brings fulfillment beyond financial success.

Sharing personal stories can open doors to genuine and authentic conversations.

3. Make it interactive

Invite your children or grandchildren to participate:

• Let each family member nominate a charity
• Give everyone a set amount to donate and present their choice
• Vote as a family and make contributions together

Even young children can weigh in with thoughtful ideas when we invite them.

4. Use real planning as a teaching opportunity

Year-end tax planning creates a natural moment to discuss:

• Charitable giving strategies (like donor-advised funds or QCDs)
• Family foundations or recurring giving
• Legacy wishes for future generations

Explaining how decisions are made is as important as the decisions themselves.

5. Keep it simple

You don’t need to review full estate plans or dollar figures on day one. The goal is connection, not complexity.

How Philanthropy Can Bring Generations Together

One of the most beautiful ways to engage the next generation is by giving them a seat at the table - both literally and figuratively.

For younger children, it may be something as simple as:

• Selecting gifts or items to donate to a holiday toy or food drive
• Volunteering as a family
• Choosing a charity from a curated list based on your values

For teens and young adults:

• Researching nonprofits and presenting their findings
• Understanding how charitable giving works and why it matters
• Discussing social impact investing opportunities
• Learning how to evaluate mission alignment and transparency

For adult children:

• Participating in donor-advised fund decisions
• Reviewing long-term philanthropic goals
• Exploring legacy letters or family mission statements

When shared purpose becomes tradition, giving becomes not just a transaction, but an identity.

Examples of Conversation Starters for Holiday Gatherings

To make initiating these conversations easier, consider questions like:

• What’s something you’re grateful for this year, and how might we help someone else experience that feeling?
• Which causes or community needs feel important to you right now and why?
• How do you define success beyond money?
• What do you think our family values most, and how could we express those values through giving?

These conversations can also transition into logistical planning naturally:

• We’re thinking of contributing to a donor-advised fund this year—would you want to help choose organizations?
• We’d like to start documenting our wishes for the future. Can we share what matters most to us and hear your perspective too?

The tone matters more than the format: open, curious, and grounded in love.

Turning Conversation Into Action: Practical Next Steps

After the conversation, consider putting structure behind intentions. For example:

Create a Family Giving Plan

Include:

• Causes you support
• Amounts or percentages
• How decisions will be made
• Legacy values and stories

Establish or contribute to a Donor-Advised Fund

Allow family members to help recommend grants and track giving impact.

Write a Legacy Letter

A heartfelt document explaining the reasoning behind your wishes, wealth, and values. Legacy letters are intended to complement, not replace, your legal estate planning documents.

Schedule a family meeting annually

It can be formal or completely casual, but consistency builds culture.

You Don’t Have to Navigate These Conversations Alone

If you’d like support facilitating family discussions about wealth, giving, or legacy planning, or would like help structuring charitable strategies such as donor-advised funds or year-end tax planning, our team at Northstar Financial Planning is here to help.

We specialize in guiding successful women and their families through thoughtful, values-based planning that supports clarity, confidence, and connection across generations.

If you’re ready to build a legacy that reflects your purpose, reach out today. 

Written by Rachel DeCarolis in collaboration with Lexicon Advisor Marketing

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