Building a Lasting Legacy: Succession & Mentorship in Financial Services with Shane Westhoelter

Amber Stitt
Nov 4
3 min read

Leaving a Legacy: Lessons from Shane Westhoelter on Pathways with Amber Stitt

There are conversations that make you stop in your tracks and rethink the way you view your career, the concept of legacy, and the impact you have on others. This episode of Pathways e3, a special edition of the Pathways with Amber Stitt podcast recorded live at the NAIFA e3 conference in Newport Beach, California, is one such conversation. Host Amber Stitt sits down with Shane Westhoelter—an industry veteran, leader, and speaker—to explore what it means to leave a legacy, the evolution of financial services, and the purpose-driven heart of the insurance profession.

The Dignity of Service

The episode opens with Shane recounting a life-changing experience early in his insurance career. He shares the story of delivering a $10,000 death claim check to a grief-stricken mother who’d lost her seven-year-old son to a drive-by shooting. Through tears, she thanked Shane—not just for the money, but for helping her keep her dignity in a devastating moment. As Shane puts it, “that was something that changed my life.” This story hammers home a powerful truth: insurance is much more than products and policies. It’s about providing dignity, security, and hope at people’s darkest hour.

Shane’s approach is grounded in service—“when everyone else is asking for money, we're bringing people checks.” He urges listeners, especially newcomers to the field, to recognize the profound importance of their work. It’s not just a job; it’s a profession that changes lives in small and big ways.

Shifting Legacy Planning

Amber and Shane discuss how legacy planning has evolved. Shane draws on three and a half decades in the field, noting that the industry is broader and more complex than ever. Legacy planning isn't just about succession or transferring wealth—it’s about shaping a meaningful, intentional narrative of your life and career.

He points out several key trends:

Longevity: With people living longer, the notion of retirement and succession has shifted. Many advisors stay engaged well past traditional retirement ages, enjoying the community and intellectual stimulation of the profession.
Identity: For so many, their career in insurance is deeply tied to their identity. The challenge is finding meaning and passions outside of work, so the transition out of business is fulfilling, not empty.
Giving Up to Go Up: Shane advocates for delegating responsibilities—to “give up, so that you can go up.” Building a team and empowering others is crucial for enjoying life and scaling impact, without losing the essence of what drives you.

Building for the Future

One of the most timely threads in the episode is the urgent need to recruit and mentor new talent in financial services and insurance. Shane calls on seasoned professionals to “reach down and pull someone else up”—to mentor, inspire, and give back so the profession remains vibrant and impactful for future generations. Amber echoes this, remarking on the reciprocal nature of mentorship and collaboration within the NAIFA community.

Shane’s advice to newcomers? Take pride in joining a profession that truly makes a difference. “We can change people's lives with a stroke of an ink pen. We can bring them money when it matters most. There are so many ways we can impactfully change people’s lives.”

Legacy Versus Wealth

When Amber asks Shane the classic question—would you rather build wealth or build a legacy?—he doesn't hesitate: “Building a legacy.” He shares his framework of four “ifs” everyone should consider: What if you live, linger, leave, or seek legacy? The lesson: wealth and possessions won’t follow you. What matters most is the legacy you design and leave behind.

Final Thoughts

This episode of Pathways e3 leaves listeners with clear action items:

For new entrants: Embrace the profession with excitement and pride; think of your work as service.
For veterans: Put operational plans in place, delegate, and focus on mentorship and philanthropy.

Shane closes with a story about Colonel Custer, who encouraged his troops to secure life insurance—a testament to early understanding of legacy. As Amber wraps up, she reminds listeners to keep taking action on their unique path.

If you’re looking for a podcast episode that will inspire you to think more deeply about career, impact, and legacy, this special edition of Pathways with Amber Stitt is a must-listen.