For Westport Lifestyle's Investment Issue, we are spotlighting individuals who help our community make, serve, and protect their investments. As there's no greater investment than a healthy life and livelihood, we spoke to Jeff Boley, an independent insurance advisor affiliated with HealthMarkets, to learn more about how he advises his clients on their insurance needs. Jeff's specialty is protecting family finances against events that are difficult to unwind later, such as death, disability, and extended care needs.
Westport Lifestyle: How did you get into the health insurance field?
Jeff Boley: Before focusing exclusively on insurance, I spent years in financial advisory and other consultative roles serving affluent clients. As an independent agent, I can objectively evaluate existing coverage for fit and ongoing value as circumstances evolve.
WL: When and why would someone want to work with an insurance agent?
JB: Most people contact a health insurance agent because they need health coverage—often due to a job change, retirement, self-employment, or a family transition. Health insurance is usually the immediate concern. In those moments, an experienced agent can help evaluate plan designs, provider networks, and formularies. What is often overlooked is that health insurance addresses only one category of health-related financial risk. While health coverage can typically be revisited each year, life insurance, long-term care, and disability coverage are far more permanent. They are also constrained by health and age. That makes structure, timing, and periodic review especially important. An agent who can address this full continuum helps families make informed decisions while flexibility still exists and coordinates those decisions with their broader financial, tax, and estate planning.
WL: What are some of the biggest decisions you help guide people on?
JB : The most consequential decisions involve long-duration risks, such as extended long-term care needs, permanent disability during peak earning years, premature death of a primary income earner, increasing longevity with rising healthcare costs, or cognitive decline requiring oversight and care. Clients seek guidance on structuring life insurance, evaluating disability income protection, and using long-term care coverage to preserve assets and flexibility. These decisions are easier to address in advance and far more costly to correct later. Because goals and circumstances change, these decisions benefit from periodic reassessment. My role is to help ensure coverage continues to reflect original intent and remains aligned with a client’s broader financial and estate planning.
WL: What are some services people may not realize they can work with an agent on?
JB: Many people associate health insurance agents primarily with health plans or Medicare enrollment—areas that can often be adjusted year to year. In practice, much of the most meaningful work involves reviewing and aligning life insurance, long-term care, and disability coverage, or identifying gaps where coverage is missing. These policies are often put in place at one point in time and left unchanged, even as assets, responsibilities, and lifestyles evolve. Health and Medicare decisions tend to be adjustable infrastructure. Life, long-term care, and disability planning benefit from thoughtful review to ensure coverage remains appropriate and sustainable.
WL: You work with both individuals and businesses. How is the process different?
JB: For individuals and families, the work focuses on protecting income, preserving assets, and planning for longevity—particularly the impact of disability, premature death, or extended care needs. For business owners and executives, life and disability coverage often intersect with succession planning, continuity risk, buy-sell arrangements, and key-person exposure, while long-term care planning influences retirement timing and capital preservation. In both cases, the process involves reviewing existing arrangements and coordinating with a client’s CPA, financial advisor, and attorney so insurance decisions support—not disrupt—the broader plan.
WL: What does “insurance as an investment” mean to you?
JB: I view insurance as infrastructure for protecting and deploying capital efficiently, not as a return-generating asset in the traditional sense. Life insurance, disability coverage, and long-term care planning exist first to absorb low-probability, high-impact events. In certain contexts, insurance can also be used effectively to meet planning objectives—such as education funding—where flexibility, tax treatment, and risk management matter. The return is not growth alone. The return is resilience and preserved options.
WL: What is the best question someone can ask when starting to work with you?
JB: A productive starting question is: “Do the insurance decisions we’ve already made still protect what matters most to us—and would they hold up if something changed?” That opens the door to a constructive review of existing coverage and coordination with the advisors already involved in the client’s planning.
WL: What are the biggest myths about your field?
JB: “If I have health insurance, I’m protected.” Health insurance covers medical costs, not income loss, long-term care needs, or the financial impact of death. “Cheapest premium equals best decision.” Focusing narrowly on premium often increases long-term exposure through higher out-of-pocket costs or coverage gaps that only appear under stress. “Insurance decisions are easy to change later.” Health insurance often is. Life insurance, disability coverage, and long-term care planning usually are not.
WL: Have you noticed shifts in what clients are looking for over the last five years?
JB: Yes. There is increased attention on long-term care risk, particularly among households that once assumed self-funding would be sufficient. There is also greater interest in confirming that existing life and disability coverage still reflects current priorities. Clients are more focused on value, sustainability, and alignment—and they appreciate guidance that fits alongside the financial and legal advice they already trust.
WL: What is your favorite part of your career?
JB: Hearing from clients after a consequential health-related event and learning that their planning prevented severe financial disruption. Those moments often follow serious illness, disability, extended care needs, or death. Much of this value is invisible when done well. It shows up later, when families realize they had more options and fewer forced trade-offs because they planned ahead and revisited those plans over time. When clients share that earlier decisions—and subsequent reviews—helped them preserve independence or maintain their lifestyle, that is the most meaningful part of my work.
For more about Jeff and his work, visit healthmarkets.com/jboley
"I view insurance as infrastructure for protecting and deploying capital efficiently. The return is not growth alone. The return is resilience and preserved options."