The transition to retirement is one of the most emotionally charged and complex periods of life. In a recent episode of March to a Million, Greg DuPont welcomes Lindsay Troxell, founder of Our Coaching Initiative, to explore how financial advisors and attorneys can add a coaching lens to their practices. Together, they discuss the critical importance of guiding clients through not just financial readiness but also the emotional and identity shifts that accompany this phase.
This conversation unveils the transformative power of coaching, the need for human connection, and how professionals can adopt practices that lead to deeper, more meaningful client relationships.
From Technical Expertise to Human Connection
The legal and financial professions often default to technical problem-solving. As Lindsay shares, the focus on numbers or legal expertise can miss an essential opportunity: addressing clients' emotional and identity needs.
Lindsay’s work began with a pivotal moment—a client who told her advisor, “You helped me confirm I can retire financially, but you missed helping me figure out what’s next emotionally.” This feedback sparked her mission to blend financial advising with coaching, enabling clients to navigate their fears, dreams, and purpose beyond the workplace.
As Greg pointed out, most advisors—and attorneys—are hesitant to “go into the soft spaces.” Yet these conversations unlock unparalleled value, transforming the client relationship into a partnership built on trust, curiosity, and emotional support.
Helping Clients Dream Beyond Exhaustion
One of the most common emotions Lindsay encounters is exhaustion. For many nearing retirement, decades of hard work leave them depleted. In such a state, dreaming about the future feels impossible.
Lindsay describes how addressing this emotional fatigue allows clients to reimagine their “second act.” For instance, one retiree discovered her exhaustion wasn’t physical—it stemmed from a belief that retirement had to resemble her working life. Once she let go of that assumption, she began envisioning a future of travel, writing, and family time.
Financial professionals can guide these breakthroughs by starting with simple but profound questions:
What are your thoughts about retirement?
When you think about retirement, how does it make you feel?
What core emotions or fears come to mind?
By meeting clients where they are emotionally, advisors and attorneys can help them rediscover their capacity to dream.
Energy Management: A Framework for Long-Term Fulfillment
Lindsay introduces a framework of energy management that resonates not only with clients but also with professionals looking to sustain their own careers:
Physical Energy: Building the foundation through proper sleep, nutrition, and movement.
Emotional Energy: Understanding and regulating emotional reactions to maintain high-quality energy throughout the day.
Mental Energy: Staying focused and mentally fit to tackle priorities effectively.
Spiritual Energy: Connecting with a deeper purpose to align actions with personal values.
For clients, this framework creates a pathway to thrive in retirement, not just survive. For professionals, it offers a roadmap to avoid burnout while delivering higher-quality service.
Coaching Questions: A Gateway to Connection
The role of an advisor or attorney is evolving. Lindsay highlights the shift from being a subject-matter expert to adopting a coaching mindset—asking open-ended questions that allow clients to explore their values and aspirations.
However, stepping into this role can bring imposter syndrome. Professionals may wonder, Who am I to ask these personal questions? Lindsay suggests reframing this discomfort:
Recognize that your role isn’t to provide all the answers but to empower the client as the expert on their own life.
Understand that these conversations are often missing in your client’s life and are invaluable to them.
As Greg notes, clients crave connection and rarely have someone who asks the deep questions about their dreams, fears, and identity.
The Role of Identity and Purpose in Retirement
Lindsay emphasizes the importance of helping clients redefine their identity post-retirement. Many struggle because their sense of self is tied to their careers. Through coaching, Lindsay helps clients identify their “core four” identities—values or roles that transcend their professional life, such as being a parent, spiritual person, or community leader.
When clients see that their identity is more than their job title, they can start to build a fulfilling purpose for their next chapter.
Practical Takeaways for Advisors and Clients
For Advisors and Attorneys:
Develop a coaching skillset to enhance your client relationships.
Start with simple, curiosity-driven questions like, What does your ideal future look like?
Practice holding space for clients, allowing them to explore their emotions and values without judgment.
For Clients:
Reflect on your own “core four” identities to understand what truly defines you beyond work.
Consider energy management as a tool for a healthier and more fulfilling life.
Explore resources like Lindsay’s 30-day Retirement Readiness Workbook to jumpstart your planning process.
The future of financial and legal advising lies in human connection. By incorporating coaching principles, professionals can not only differentiate themselves in a competitive market but also make a lasting impact on their clients’ lives.
Whether you’re an attorney exploring this new role or a client seeking clarity for the next phase of life, the key takeaway is clear: meaningful conversations about identity, purpose, and energy create a foundation for lasting success and fulfillment.
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