About the Exploring Series

The Exploring Series from 21/64 (in collaboration with Relative Solutions) is designed to spark meaningful conversations about philanthropy, wealth, and values across generations. Each deck of 50 thoughtfully crafted question cards creates a safe, engaging, and flexible framework for discussion — whether one-on-one, with family, or in group settings.

Unpack the meaning of wealth with openness and clarity.

Exploring Wealth helps families, advisors, and boards engage in conversations about one of the most complex and sensitive topics: wealth itself. With 50 thought-provoking question cards, this tool creates a safe space to reflect on role models, motivations, and values — and to foster understanding across generations.

What’s included

• Deck of question cards for reflection and discussion.
• “How to Play”, “Ways to Play” and “Next Steps” instructions included to guide individuals or groups in using the tool effectively.
• Cards can be selected and sorted to identify the legacy that resonates most.
• High-quality, recycled materials, printed in the U.S.
• Facilitates individual reflection, small group exercises, or large group discussions.

How it works

• Deck of 50 open-ended question cards focused on wealth and its many dimensions.
• Encourages dialogue about role models, values, motivations, and experiences of wealth.
• Helps participants articulate what wealth means to them and how they want to use it.

Who it’s for

• Families exploring values and legacy across generations.
• Advisors, family offices, and foundation boards seeking structured wealth dialogue.
• Facilitators guiding groups through sensitive wealth conversations.

Use it in practice

• Sort and choose cards that asks a question you feel comfortable discussing, then one you’re curious to explore further.
• Use in one-on-one or group sessions to catalyze dialogue and insight.

Pairs well with

• Exploring Giving
• Exploring Next Gen Donors
• Motivational Values

See it in action
Experience how Exploring Wealth can deepen family or client conversations at our 21/64 Managing Family Dynamics and Talking About Money Training, where we model facilitation techniques and strategies for navigating sensitive topics.

Click here to download the a complimentary Facilitator’s Guide.