Leadership, Legacy & Giving with Intention | Deborah Goldstein’s Uncommon Philanthropy Journey

What does it really mean to give with intention—and how can generosity become a conscious practice that shapes your legacy?

In this episode of (un)conversations®, Dr. Alison Schmidt sits down with Deborah Goldstein, Founder of Enlightened Philanthropy, to unpack the mindset, meaning, and magic behind purpose-driven giving. With more than 25 years in the nonprofit sector, Deborah has guided individuals, families, and next-generation leaders to build clarity around their values, deepen connection, and create impact that lasts.

Through the lens of the (UN)word Effect, Deborah shares how being (un)deterred, (un)prepared, and (un)common helped shape her path as a leader, philanthropist, and entrepreneur. This conversation challenges the myth that philanthropy is only for the wealthy—and shows how intentional generosity can transform lives at any level.

Whether you’re navigating family philanthropy, building a foundation, exploring nonprofit leadership, or seeking more meaningful ways to give, this episode offers a fresh, grounded, and inspiring perspective on legacy and leadership.

✨ Episode Takeaways

• 🌱 Giving with intention creates meaningful, lasting legacy

• 🧩 The (UN)word Effect as a tool for personal insight and self-leadership

• 💎 Philanthropy is for everyone—not just those with excess wealth

• 🚀 Being (un)deterred fuels purpose, resilience, and entrepreneurial courage

• 🤝 Vulnerability is the gateway to authentic (un)conversations

Timestamps:

(00:00) Introduction to Disruptive Leadership
(01:10) The (UN)word Effect: A Journey of Self-Discovery
(07:22) Uncommon Paths: Embracing Uniqueness in Career
(16:37) Undeterred: Pursuing Dreams Against the Odds
(21:54) Navigating Internal Conversations & Leaping into Entrepreneurship
(32:31) Resilience in the Face of Doubt
(33:27) The Journey of Enlightened Philanthropy
(35:38) Embracing Unpreparedness in Business
(42:35) The Power of Understated Excellence
(46:10) Unwavering Commitment to Philanthropy
(55:11) Creating Meaningful Philanthropic Experiences
(1:03:05) The (UN)wrap up & Outro

About the Host & Guest:

Dr. Alison L. Schmidt, CEO of Unconvention and host of (un)conversations®, Alison empowers leaders and organizations to unlearn what no longer serves them—and lead with authenticity, courage, and purpose.
Website: www. unconventionllc.com
Deborah Goldstein, Founder of Enlightened Philanthropy, Deborah helps individuals and families bring clarity, intention, and heartfelt purpose to their giving—strengthening legacy, values, and connection across generations.
Website: www.enlightenedphilanthropy.com

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