Welcome back to Don’t Retire… Graduate! On today’s episode, we’re excited to bring you another entry in our “Diary of a Financial Advisor” segment, where we spotlight the unique voices, journeys, and motivations of financial professionals passionate about their clients’ success. I had the pleasure of sitting down with Jillian Howell, a rising star at BFG Financial Advisors and one of the dedicated Client Service Associates who keeps everything running smoothly for nearly 800 families nationwide.

Jillian joined BFG in March 2025, bringing with her a Bachelor of Arts in Communication Studies (with a minor in general business) from the University of Maryland, College Park. Her background sets her apart, blending strong communication skills with a desire to help others achieve financial well-being. Throughout our conversation, Jillian shared her journey from a family full of pharmacists (and her conscious decision to blaze her own path), her early experience engaging clients in the T. Rowe Price call center, and the drive to bring accuracy, care, and continual learning to her current advisory role.

We dove into what it’s like to enter the nuanced world of insurance, the importance of always being a “sponge” for new knowledge, and the unique challenges of juggling countless client needs under pressure. Jillian also opened up about her “why”—drawing inspiration from a late high school mentor who guided her into the business world—and how she channels that legacy in her work every day. Outside the office, we got a glimpse of her adventurous spirit, love for skiing, and her golden retriever, Beau.

If you’re curious about the people working behind the scenes to deliver exceptional service and guidance, you won’t want to miss Jillian’s perspective on finding purpose in financial planning, building client relationships, and balancing detail-oriented work with meaning.

5 Key Takeaways:

1. Charting Your Own Path: Jillian illustrates the courage and clarity needed to pursue a career that aligns with your natural strengths and interests, even when it departs from family tradition.
2. The Power of Being a Sponge: Whether starting out or pivoting to new areas—in Jillian’s case, insurance and annuities—success comes from humility, curiosity, and a commitment to learning from seasoned professionals.
3. Client Service at Its Core: Jillian’s journey underscores how detail-oriented, empathetic support can make a real difference in clients’ lives—whether helping with urgent distributions or navigating the intricacies of insurance.
4. Finding Your ‘Why’: A personal “why”—rooted in relationships, legacy, and the desire to make others proud—fuels growth and resilience, especially in a demanding service environment.
5. Building Relationships Beyond the Screen: Even in today’s world of digital forms and remote service, Jillian demonstrates that taking time to get to know clients personally, whenever possible, adds an invaluable human touch to financial advice.

Join us for an inspiring look behind the curtain, and meet the people who help families graduate into retirement with confidence and care. Don’t forget to subscribe, rate, and share this episode with anyone who values the dedicated professionals guiding their financial futures!

Welcome back to Don’t Retire… Graduate! In today’s episode, we’re deep diving into the power of money conversations—why talking about your finances is crucial, and how it can serve as the foundation for a life of financial independence and fulfillment. Joining me is Skyler Fleming, financial coach and host of the “Money Talk with Skyler Fleming” podcast. With over 150 episodes under his belt and firsthand experience working his way up in a credit union, Skyler has become an enthusiastic advocate for breaking the taboo around discussing money and making finance approachable for everyone.

During our conversation, Skyler and I explored how simple, honest conversations can be the gateway to better financial habits, awareness, and ultimately, confidence. Skyler shared his journey, from fielding frustrated calls at a credit union to helping everyday people master their money both one-on-one and through podcasting. We unpacked his signature “seven money talking points,” covering everything from emergency funds and tracking your cash flow to the big philosophical questions about debt and financial goals. We compared coaching versus planning, debated the age-old question of whether or not to pay off debt early, and dove into how technology and automation can make managing your finances easier and less intimidating.

We also discussed mindset shifts through each life stage—why younger folks might want to maximize cash flow and debt leverage, while those closer to retirement may crave the security of being debt-free. Skyler and I both underscored the importance of not just focusing on retirement, but also on all the fun and meaningful goals that happen along the way: dream vacations, supporting your community, or funding your kids’ education. Ultimately, whether you’re in a partnership or on your own, we talked about building your own “money buddy” system for accountability and growth.

5 Key Takeaways:

1. Start Money Conversations Early and Often: Breaking the taboo and having simple, honest money talks—whether with a partner, friend, or coach—can demystify finances and set you up for success, no matter your starting point.
2. Master the Seven Money Talking Points: Skyler’s framework covers crucial questions: your emergency strategy, how you make, spend, and save money, your approach to debt, what you want your retirement to look like, and your big, aspirational financial goals.
3. Automation and Tracking Are Allies: Whether you love spreadsheets or apps, regularly tracking income and expenses—and leveraging automation—can take the pain out of budgeting and ensure your money goals stay on track.
4. Debt Decisions Are Personal: The question of paying off debt isn’t just about numbers; psychology and life stage play huge roles. Make debt payoff decisions based on your comfort, goals, and current opportunity costs, not just the math.
5. Design the Life You Want—Not Just a Retirement: Planning isn’t limited to the finish line of retirement. Identify and segregate funds for your “big money goals,” and build systems (and buddies!) to stay accountable and intentional every step of the way.

Join us as we explore how a little financial transparency and proactive planning can empower you to live with passion and purpose—today, in retirement, and every step in between. Don’t forget to subscribe, rate, and share this episode with anyone eager to have their own “money talks” and transform their financial future!

1. Representation Matters in Finance: Manny highlights the visible lack of diversity in financial planning, and how seeing few role models in the industry can limit a young person’s belief in the possibilities for their own career.
2. The Power of Exposure and Mentorship: Manny’s journey was shaped by mentors and chance encounters—emphasizing that if you don’t know a career exists, you can’t prepare or aspire to it. Intentional outreach and speaking at schools can create these vital opportunities.
3. Apprenticeship Over “Sink or Swim”: Rather than the traditional approach of pushing new advisors to sell right out of the gate, BFG’s apprenticeship model focuses on gradual learning, client exposure, and holistic development—leading to better advisors and better client outcomes.
4. Excellence Over Perfection: Manny distinguishes himself by expecting perfect effort, not perfect performance, from himself and those around him. He believes in holding high standards while understanding that learning and growth are ongoing processes.
5. Paying It Forward: Manny is committed to giving back—returning to his alma mater, educating others about financial literacy, and striving to be a first-call advocate and steward for his clients and community. He believes true luck and success come at the intersection of preparation and opportunity.

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.

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.

1. Redefining Retirement as Graduation: I shared my belief that retirement shouldn’t be a retreat, but a “graduation” into something even better—another chapter of purpose, relevance, and contribution, no matter your age or stage.
2. A Legacy Built to Last: One of my greatest professional aspirations is to build a legacy at BFG that not only endures but thrives beyond my own career and lifetime, continuing to serve clients and foster great talent.
3. The Power of Mentorship and Collaboration: Modeled after a teaching hospital, BFG offers advisors a place to learn and thrive without pressure to “sell”—demonstrating that collaboration and ethical mentorship are the cornerstones of a meaningful career.
4. The Critical Need for Financial Literacy: Navigating the financial world requires knowledge and vigilance. I highlighted accessible resources like our free online financial literacy course at BFG University and recommended involvement in programs like Junior Achievement to help bridge the gap.
5. Choosing the Right Financial Advisor: When seeking an advisor, trust and transparency are paramount. I cautioned listeners to seek professionals who are honest, open, and clear about their offerings—making the advisor-client relationship as authentic and supportive as possible.

1. Money Is a Mirror, Not a Monster: Chelsea drives home that financial problems often reflect deeper issues like boundaries, communication, or beliefs—money simply brings these patterns to the surface.
2. Women Are Reshaping Financial Power: Despite only recently entering the world of independent finance (about 1% of the time financial institutions have existed!), women now control a growing share of wealth and are learning to own their money narratives.
3. Pay Yourself First—Every Time: Whether personally or in business, prioritizing savings before spending allows you to break the common “net zero” habit and set yourself up for long-term success—even if you’re only saving “50 cents at a time.”
4. The “B Word” Isn’t About Restriction: Creating a budget—whether for a business or household—is about establishing boundaries and protecting your future self, not about deprivation. Think of it as building freedom within guardrails you create for yourself.
5. Financial Planning Is an Ongoing Art: No plan can predict the future perfectly—what matters is having a clear “shot to call,” monitoring and adjusting regularly (even quarterly check-ins can make a big difference), and being comfortable with pivoting as life happens.