Steering Your Financial Future: Demystifying Life Settlements with Christopher Conway

Amber Stitt
Jul 1
3 min read

Navigating Life Settlements: Myths, Real-Life Stories, and the Course-Correcting Approach to Financial Planning

On the latest episode of "Pathways with Amber Stitt," Amber sits down with Chris Conway, a seasoned expert in the life settlements industry, for a candid and insightful look at what life settlements really are, who they serve, and why understanding them could be a game changer in your financial or advisory toolkit.

If you’ve ever felt like insurance is a dry, confusing necessity—or questioned its actual value—this episode is for you. Chris’s own story of stumbling into the life insurance world in the early 1980s, and then questioning the status quo until he found his niche, sets the stage for an open-minded look at what too often is an overlooked financial asset: your life insurance policy.

Understanding Life Settlements: The Big Myth

A key message from Chris is the persistent myth that life insurance is a liability—a bill to pay, a product you only need for as long as you have dependents, and then it’s "done." Chris flips this narrative entirely: "Life insurance is an asset," he says. The opportunity to sell a policy you no longer want or need—a regulated process called a life settlement—can turn that supposed liability into a real asset with tangible value, oftentimes much more than a policy’s cash surrender value.

In fact, Chris points out, on average, a life settlement pays out six times more than a policy’s surrender value. The transaction is straightforward: an investor takes over the policy’s premiums and, in return, receives the death benefit eventually, while the seller (the policyholder) gets a lump sum payment now, putting otherwise dormant value into action.

Why Investors Buy—and Why Policyholders Sell

Some listeners might wonder, "Why would anyone buy my life insurance policy?" That’s where Chris’s watchmaker mind shines; he explains it’s all about portfolio balance for investors. Life settlements offer yield and diversify risk—they don’t correlate with the stock or bond markets, making them attractive to institutional investors looking for alternative assets.

On the other side, the typical sellers are often older individuals who find that their financial needs or goals have shifted. They may be looking to cover healthcare or long-term care costs, pay off debts, or simply want to make the most of their golden years—yes, sometimes even taking the family on that once-in-a-lifetime cruise with the proceeds.

Breaking Down Barriers: Who Should Know About Life Settlements?

Amber and Chris both emphasize that understanding life settlements isn’t just for the wealthy. While the market began with large policies from affluent individuals, more and more ordinary people are benefiting as awareness grows and minimum policy sizes drop. Direct-to-consumer models have made this financial tool more accessible than ever.

For financial advisors, not knowing about life settlements is a missed opportunity—not just for revenue, but for real service to their clients. Chris encourages advisors to add this knowledge to their toolbox, and even use life expectancy assessments to provide more personalized, strategic planning as longevity grows and retirement becomes more complex.

The Importance of Course-Correcting

Chris draws a vivid analogy near the end of the episode—navigating finances and life is like steering a boat on the ocean. Forces are always shifting; you can’t set your strategy and walk away, or you risk drifting off course. Periodic course corrections are essential. This is where having access to tools like life settlements and customized life expectancy assessments can make all the difference. It’s about knowing where you are and choosing the best path forward at every turn, rather than relying on outdated plans or standardized advice.

Take Action: Be Proactive, Not Reactive

Amber and Chris’s conversation is a call to action—whether you’re a consumer or an advisor—to be proactive about planning. Get comfortable discussing not just the "what do I need?" but "what do I want?" Plan for your healthspan as well as your lifespan, know your assets, and don't be afraid to ask questions or seek out specialists when you meet new crossroads.

Stay tuned to "Pathways" for more empowering conversations on navigating life’s complex choices.

Remember, your financial journey isn’t about set-it-and-forget-it. It’s about steering, questioning, and optimizing as you go—making sure you, not the currents, chart your course.