Douglas Tsoi on Finding Financial Freedom, Meaning, and Community

Highly Sensitive Money with Diana Gisel Yañez

Douglas Tsoi on Finding Financial Freedom, Meaning, and Community

In this episode, our guest Douglas Tsoi and I dive into the intersection of financial freedom, personal values, and social impact. Douglas, founder of the School of Financial Freedom, shares his journey from lawyer to educator, achieving financial independence by living simply and intentionally. Together, we unpack how his minimalist philosophy allowed him to pursue a path focused on meaning and community. As he shares stories of his family’s immigrant history and insights from his own life transformations, Douglas invites listeners to rethink the roles of money, work, and community in their own lives.
Finding peace and purpose beyond financial independence can be elusive, but in this conversation, Douglas Tsoi offers a fresh perspective on how financial freedom opens the door to more meaningful pursuits. Rather than seeing wealth as an end goal, Douglas invites us to explore our motivations and embrace a simpler, more intentional life.

Meet Our Guest

Douglas Tsoi is the founder of School of Financial Freedom. This is his short financial freedom story: After college, he had careers as an intellectual property lawyer, Quaker school teacher, government sustainability officer, and nonprofit training manager, making an average of $36,000 a year. During all that time, he lived on $20,000 a year for 20 years and invested the rest. At age 42, he “retired.”
After FI, Douglas spends most of his time playing soccer, writing, traveling, and hanging with his dog Wu Wei. He also started a Portland Underground Grad School, a place for affordable lifelong community and education. He became a Franciscan Spiritual Director, trained as a hospital chaplain, and does financial-spiritual coaching. He created The Appreciation Effect, the Gratitude Dojo, and a reparative justice fund. His principle values are voluntary simplicity, integrity, gratitude, lifelong learning, and community.
Beyond his financial achievements, Douglas is a multifaceted thinker and leader, committed to building connections and inspiring personal growth. He founded the Portland Underground Grad School to foster lifelong learning in his community and offers financial-spiritual coaching through his roles as a Franciscan Spiritual Director and sustainability advocate. In line with his principles, Douglas has created community-based initiatives such as The Appreciation Effect, the Gratitude Dojo, and the Jubilee Fund, aiming to address systemic financial challenges and bring awareness to the ethics of consumption. Through these projects, Douglas embodies a life of purpose, balance, and meaningful contribution.

Highlights

[00:00:30] Why Douglas founded the School of Financial Freedom
[00:02:10] The role of inner longing in financial decisions
[00:06:50] Douglas’s family’s immigrant history and money trauma
[00:08:20] Learning to live on “enough”
[00:09:50] Money vigilance and scarcity in immigrant families
[00:13:20] Ethics of consumption vs. investing
[00:15:30] How capitalism affects our identity
[00:19:50] Supporting family without losing oneself in “workism”
[00:24:50] Balancing giving with self-care
[00:27:50] From corporate lawyer to Quaker teacher
[00:33:20] Social justice through spiritual interconnectedness
[00:34:50] Applying spiritual principles to financial education
[00:36:50] The challenge of finding purpose after financial independence
[00:39:20] The value of analog leisure and true rest
[00:47:00] Building community through the Jubilee Fund
From his work at the School of Financial Freedom to the creation of the Jubilee Fund, Douglas’s approach is not about financial shortcuts but about building a life rooted in values of community, gratitude, and enoughness. This episode challenges conventional ideas of success, exploring the emotional aspects of capitalism and the liberating power of “doing nothing.” Tune in for an insightful discussion on rethinking our relationships with money, work, and each other to live fuller, more purposeful lives.

Resources

Douglas Tsoi
Substack
School of Financial Freedom
Scarcity: Why Having Too Little Means So Much by Sendhil Mullainathan and Eldar Shafir

Diana Gisel Yañez is an Investment Advisor Representative of Natural Investments PBLLC. Natural Investments is an independent Registered Investment Advisor. All the Colors is not a registered entity and is not an affiliate or subsidiary of Natural Investments. See our Disclosures and Disclaimers and read our Form CRS.