This program is offered as a Members ONLY benefit to Florida Diamond and Sapphire Members!
HealthCare Coverage – Understanding your Options at Every Stage of Life
September 15, 2026 | 6:00 pm – 8:00 pm EDT
Healthcare can be complicated, particularly when we experience a life or career transition. You may have excellent coverage through your employer today, but what happens if you change jobs? What if you become self-employed? What if you retire before you’re eligible for Medicare? And once you reach Medicare eligibility, how do you decide among the different options?
Rather than talking about healthcare insurance strictly in terms of products and policies, we’re going to look at four common situations:
- I’m employed and choosing my benefits.
I’ve left my job and need healthcare coverage.
I’m self-employed or don’t have employer-sponsored coverage.
I have parents trying to navigate Medicare or I am approaching retirement age and need to understand Medicare options
We’ll also talk about Health Savings Accounts—or HSAs—and how they can play a role not only in paying today’s healthcare expenses but also in longer-term financial planning
And, importantly, this event is an opportunity to ask questions. Our hope is that everyone leaves with a better understanding of what questions to ask and where to go for help when making these decisions.