On this episode of Financial Behavior Thought Leaders, host Dr. Mary Bell Carlson welcomes Jonathan Ainsley, a renowned keynote speaker with over 40 years of experience in the financial services industry. Jonathan is known for his transformative approach to financial planning, inviting both advisors and their clients to reimagine what it means to age, connect with technology, and deepen our relationships with ourselves and others. This episode goes behind the scenes of Jonathan’s unique perspective, unpacking his signature framework—the “three revolutions”: flourishing longevity, technology’s disruptive power, and the shifting landscape of relationships.

Mary and Jonathan begin with his personal journey, tracing his fascinating career path from bond broking and day trading featured in the Wall Street Journal to deep expertise in practice management at top firms like SunTrust, Schwab, and Merrill Lynch. Jonathan shares how his own discomfort with public speaking transformed into a passion for inspiring audiences, particularly around the profound societal shift from traditional retirement models to longevity planning. Mary and Jonathan delve deeply into how longevity, in both mindset and practical terms, is changing financial services—and why financial advisors must evolve to meaningfully guide clients across decades, not just dollars.

They discuss the growing need for financial professionals to go beyond numbers and embrace a holistic, human-centered approach. By weaving together stories from his workshops and keynotes, Jonathan illustrates how both advisors and clients have been profoundly changed when encouraged to think expansively about their futures. The conversation also explores the challenges—and opportunities—presented by AI and rapidly advancing technology, as well as the essential inner work advisors must undertake to serve clients fully.

Five Key Takeaways:

1. Longevity Planning is the New Frontier - Jonathan urges advisors to transcend the outdated retirement model and embrace “longevity planning.” With people living longer, more vibrant lives, he believes the industry must shift from simply ensuring clients don’t outlive their money to helping them thrive for up to four additional decades. This means encouraging clients to envision what living well across a 40-year “bonus round” could truly look like—and aligning financial, health, and personal goals accordingly.
2. The Power and Disruption of Technology - AI and technology are not just tools—they’re revolutionizing the advisor role. Jonathan emphasizes that while AI can take over knowledge and analytical tasks, the irreplaceable value advisors bring is wisdom, empathy, and the human touch. Advisors must focus on building trust, facilitating change, and supporting clients through emotional and psychological transitions, not just monetary ones.
3. Flourishing Longevity is Holistic - True flourishing in later life is about much more than financial metrics. Jonathan’s work recognizes the critical importance of metabolic health, mindset, purpose, community, and financial fitness—what he calls the six pillars of flourishing longevity. Programs and tools like his Flourishing Longevity Scorecard and the “InvestinU” platform help clients and advisors holistically assess where they are and create actionable strategies for growth in all areas of life.
4. Relationships and Inner Work Drive Fulfillment - One of Jonathan’s most powerful insights is that the third “revolution” is relational—both our connections with others and with ourselves. As the nature of career and life stages evolves, fulfillment becomes a central goal. Advisors must address not just client portfolios, but also purpose, resilience, community, and helping clients navigate personal transitions. Importantly, this requires advisors to do inner work themselves: addressing their own fears, beliefs, and aspirations so they can authentically support others.
5. Real Transformation Requires Action and Sustained Engagement - Jonathan goes far beyond inspiring keynotes—he’s committed to creating ongoing, measurable change for both advisors and clients. He offers training programs, workshops, and experiential journeys (such as the NASA-approved 12-module CE program), along with practical self-assessment tools. The feedback is resounding: advisors report newfound purpose, engage clients in deeper ways, and see business impact through increased referrals and client satisfaction.

This episode is a must-listen for financial professionals, event planners, and anyone seeking to understand—and leverage—the profound shifts shaping the future of aging, technology, and financial advice. Jonathan Ainsley’s story, expertise, and generously shared frameworks offer inspiration and tangible next steps for creating a truly human—and impactful—financial services experience.

If you’re seeking a speaker who brings not just expertise, but genuine transformation to your organization or clients, Jonathan Ainsley is helping folks unlock new possibilities—at work and in life.