Welcome back to Don’t Retire… Graduate! In today’s episode, we dive into the intersection of estate planning, philanthropy, and building legacies—especially within underrepresented communities. I’m joined by the remarkable Shari Fleming, an estate planning attorney and philanthropic advisor whose passion for service, education, and bridging community gaps is truly inspiring.

Shari’s credentials are impressive: Magna Cum Laude graduate of Lincoln University with degrees in History and Black Studies, J.D. from the University of Maryland School of Law, Accredited Estate Planner, and Chartered Advisor in Philanthropy. In addition to her own thriving law practice, she serves as the Planned Giving Officer at Bowie State University and founded the “Our Legacy Matters” community to advance ownership and generational wealth in communities of color.

In our conversation, Shari and I explored her unconventional path to law, sparked not by an early passion but by process of elimination and an urge to help others. We discussed how her two worlds—the professional estate planning sphere and her home community—often felt disconnected, leading her to create “Our Legacy Matters” as a bridge built on accurate, accessible information.

Shari described how her practice begins with clients’ intentions and dreams, not just the technical “tools” of estate law. We addressed the deeply personal side of philanthropy and why time, talent, and treasure all play crucial roles in building legacies, especially when generational conversations about giving may look different across cultures. She also touched on the challenges of building a solo practice, the critical influence of true mentors, and her commitment to mentoring the next generation of diverse professionals.

We also talked honestly about work-life balance, the importance of joy, and her decision to hit “pause” and reflect after years of hard work—while keeping her eyes on new dreams, including the possibility of a book!

5 Key Takeaways:

1. Philanthropy Is Personal: Shari emphasized that charitable planning always begins with the client’s unique intent and dreams—never just the technical tools. Professionals must listen deeply to turn intentions into meaningful strategies.
2. Bridging Community Gaps: Recognizing the disconnect between the professional estate planning world and communities of color, Shari founded “Our Legacy Matters” to provide a safe, educational space and bridge miscommunication with accurate, accessible information.
3. Mentorship Matters: A pivotal relationship with her mentor, Aquanetta Betts, shaped Shari’s career and underscored the value of seeking (and becoming) lasting mentors, especially for those without inherited networks or practices.
4. Redefining Generational Philanthropy: Philanthropy in underrepresented communities often centers more on service, time, and talent than on financial gifts—yet these are powerful forms of legacy that deserve recognition and strategic support.
5. The Power of Joyful Reflection: Success isn’t just about relentless achievement. Shari’s decision to pause and intentionally reflect—to “let the sun shine” and dream anew—shows how purposeful rest and pursuit of joy are essential for continued growth.

Join us to discover how intention, compassion, and strategic planning can help you not only secure your family’s future, but also uplift your community and find fulfillment along the way. Don’t forget to subscribe, rate, and share this episode with those on a journey to transform their legacy—financially and beyond!

1. Diverse Career Paths in Finance: Lena emphasized that the financial services industry offers far more than just becoming an advisor. Roles in client relations, marketing, operations, and research are all vital, making it a great field for a wide variety of skill sets and interests.
2. Mentorship and Representation Matter: As someone who experienced firsthand the lack of female role models early on, Lena is committed to mentoring young women and creating pathways for them to succeed in finance. She encourages firms to offer shadowing and internship opportunities to expose students to the real-world variety of financial careers.
3. Collaboration Drives Better Decisions: One of BFG’s guiding principles is collaboration—not just among leaders but across all levels of the organization. Lena explains how inviting input from every team member, including interns, leads to richer discussions, stronger decisions, and a healthy workplace culture.
4. The Value of Study Groups and Advisory Boards: Peer study groups, especially those focused on elevating G2 (second-generation) women leaders, are becoming important spaces for learning and growth within finance. Lena acknowledges that both male and female advocates are needed to accelerate industry-wide change.
5. Progress Toward Inclusion: While change is happening, Lena notes that the industry still has a long way to go to achieve true diversity. She urges firms to look beyond appearances and seek diversity in experiences, perspectives, and education as well as backgrounds, ultimately enabling better connections with a diverse client base.

1. Start Early, Start Small: Don’t wait for a crisis to begin decluttering and downsizing. Tackle one room or even one pile at a time, and if you’ve lived in a home for decades, plan for at least a month per decade to manage the process without unnecessary stress.
2. Professional Organizers as Allies: Hiring a reputable, experienced organizer (often through the National Association of Productivity and Organizing Professionals) gives you access to trusted resources, emotional support, and systems for uncovering and preserving valuables as well as clearing out everything else effectively.
3. Treasures Among the Chaos: It’s common for teams like Tara’s to discover valuable items such as forgotten life insurance policies, coins, stock certificates, or important documents—sometimes totaling tens of thousands of dollars or more. Properly sorting and investigating paperwork can truly pay off.
4. Involve the Family and Give Back: Downsizing isn’t just about “stuff”—it’s also a chance to talk about memories, philanthropy, and family storytelling. Regular purges, creating donation bins, and thoughtfully redistributing goods keeps giving at the center of the process.
5. The Power of Three Friends: For peace of mind, identify three trusted people: one who knows your finances, one who knows your passwords, and one who knows about any “secret stuff.” This trio can help ensure your legacy and information are handled as you wish in any emergency.