Leading with Purpose: Sherwin Sargeant on Serving Florida’s State and Education Employees

Sherwin Sargeant is a seasoned retirement planning professional and the visionary founder of Sherwin and Associates, a firm respected for its tailored services to education and state employees in Florida. With a mission to empower clients enrolled in the Florida Retirement System, Sargeant leverages his expertise to craft personalized strategies that help them achieve their financial goals. 

He is a Diamond Club Member recognized by National Life Group, and his exceptional work in the field has solidified his reputation as a trusted authority. Sargeant is an alum of the University of Central Florida and has a CFP in Finance. His professional endeavors extend to ownership of Zingara Souls, a boho glam boutique in Winter Park, Florida. His versatility and dedication to clients is reflected in his commitment to making a lasting impact on all he serves.

How did you get into the business of retirement planning and working with Florida school districts?

Twenty years ago, I embarked on a journey into retirement planning with a specific focus on serving Florida school districts. The inspiration came from the realization that Florida’s educators – those shaping the future generation – were largely underserved when it came to financial literacy and retirement preparedness. 

Despite their dedication to teaching and nurturing students, many teachers lacked access to the resources and guidance necessary to secure their financial futures. At the time, I observed a critical gap in the financial services industry. Teachers were under-informed about the options available to them but were also often overlooked by mainstream financial advisors. They faced unique challenges, including understanding the complexities of pension systems, navigating supplemental retirement savings plans, and balancing these with the demands of their modest incomes. 

Recognizing this underserved need, I saw an opportunity to make a meaningful difference by providing the tools, knowledge, and support these educators needed to build a secure financial foundation. My journey began with a commitment to bridge this gap. I dedicated myself to understanding the Florida Retirement System (FRS) and the specific financial challenges faced by educators. 

Over the years, I developed a tailored approach to retirement planning, focusing on educating teachers about their benefits, helping them optimize their savings strategies, and empowering them to make informed financial decisions. Working closely with school districts, I established partnerships that allowed me to deliver.

What is something you do regularly in your retirement planning practice that you would recommend to others in your field?

Staying motivated in my field requires setting clear, actionable goals that align with long-term vision. Focus on personal growth by seeking out challenges that keep you engaged and inspired. It’s also important to Celebrate small wins to maintain momentum and reinforce your achievements. When you surround yourself with positive influences and peers who encourage you to strive for excellence, you can more clearly see and regularly reflect on your “why” – the purpose and passion that fuel your commitment to providing the best services to FRS employees.

Being a requested advisor requires developing deep expertise by staying current with industry trends and continuously improving your knowledge. You must build credibility with strong partners to deliver consistent results, integrity, and professionalism. Foster strong relationships by listening actively, empathizing, and offering tailored advice. Demonstrate reliability by following through on promises and delivering high-quality work. By focusing on each – whether it’s a school bus driver, teacher, paraprofessional, principal, or superintendent – you create lasting value. Balancing motivation with trust-building allows you to excel while earning respect and loyalty from those you work with.

What do you consider to be the most common challenges Florida’s education professionals face when planning for retirement, and how does your firm address these challenges?

One of the significant challenges facing the education profession today is the lack of financial security among teachers, particularly due to insufficient retirement savings. Many educators, despite their dedication to shaping future generations, often do not prioritize saving for their own futures. This issue stems from limited financial literacy, competing financial obligations, and the absence of accessible savings mechanisms tailored to their unique needs.

To address this issue, I am actively working to implement an auto-enrollment retirement plan specifically designed for the educational community. This initiative would ensure that every teacher has access to a structured and manageable way to save for retirement.

Teachers would be automatically enrolled in a retirement savings plan upon employment, ensuring they start saving without requiring proactive action. Participants can adjust their contribution levels based on their financial situation, providing flexibility while promoting consistency. The plan includes resources to improve financial literacy among educators, empowering them to make informed decisions about their financial future. I am collaborating with school administrations and financial institutions to establish these plans at minimal cost, ensuring accessibility and sustainability.

This solution addresses the root of the problem by removing barriers to saving and embedding a culture of financial responsibility within the profession. By helping teachers secure their financial future, we also contribute to a more focused and less financially stressed workforce, which ultimately benefits the educational system as a whole.

Looking back on the last five years of your career, what has been the highlight?

Over the last five years, the highlight of my career has been helping over 500 educators retire successfully. This experience has been about much more than numbers as it’s centered on fostering meaningful relationships, providing peace of mind, and ensuring financial security. By guiding educators to build a reliable stream of income in retirement, I’ve been able to help them transition confidently into this new chapter of life, knowing they are set up for long-term success and stability.

What does a typical day look like for you as a retirement planning expert and financial advisor?

A typical day for a Retirement Representative revolves around assisting clients with their retirement planning needs, managing a busy schedule, and staying on top of various tasks. The day often begins by meeting with clients – either in person, over the phone, or virtually – to discuss their retirement goals. This involves actively listening to their concerns, gathering financial details, and assessing their current retirement plans to identify gaps or opportunities. 

With numerous appointments and follow-ups to handle, maintaining an organized calendar has proved essential. A typical day includes scheduling consultations, preparing for upcoming meetings, and ensuring all commitments are met on time. Managing and prioritizing referrals is a key aspect of the role, and reaching out to potential clients, setting up introductory meetings, and ensuring a consistent flow of new leads into the pipeline are ongoing tasks. 

Between meetings, my time is spent analyzing client data to tailor personalized retirement strategies. This includes reviewing investment options, insurance plans, and other financial products. A portion of the day involves collaborating with team members or other professionals, such as financial advisors or estate planners. Additionally, documenting interactions and maintaining accurate records in CRM systems is a crucial part of the job. In essence, a Retirement Representative juggles client interactions among other important tasks that help clients meet their goals and find retirement planning success.