5 key health care strategies for clients who want to retire early
5 key health care strategies for clients who want to retire early
Retiring early is a dream for many — and an unexpected reality for some. According to the Employee Benefit Research Institute (EBRI), half of retirees say they retired earlier than expected. Regardless of intent, the median age at which Americans retire is 62.1 Retiring early can leave a potentially significant gap in health care coverage before Medicare eligibility begins at age 65.

COBRA, or the Consolidated Omnibus Budget Reconciliation Act, allows individuals to temporarily continue their employer-sponsored health insurance after they retire. This coverage is available for up to 18 months (and can be extended to 36 months in some cases). While it covers the same health services your client had access to while working, it also comes with higher costs. Typically, retirees pay the entire premium themselves, plus a small administrative fee (whereas while they were working, their employer probably paid the majority of the premium).
Though COBRA is often more expensive than what people pay as employees, it can still be a convenient way to bridge the gap until Medicare coverage begins. Retirees don’t have to change doctors or deal with a new insurance plan, which simplifies things during the transition into retirement.
That said, it’s important to compare the cost of COBRA with other coverage options, such as plans through the Health Insurance Marketplace, to ensure the most cost-effective choice.

For clients who contributed to an HSA during their working years, that account could be a valuable resource to help them cover health care expenses before Medicare. HSAs offer a triple tax advantage — contributions are tax-deductible, earnings grow tax-free and withdrawals for qualified medical expenses are also tax-free. This makes them one of the most efficient tools for managing health care costs in retirement.
HSA funds can be used for a wide range of qualified expenses, including doctor visits, prescription medications and even long-term care premiums. Unlike flexible spending accounts (FSAs), HSAs have no “use-it-or-lose-it” rule, meaning any unspent funds roll over each year and remain available even after retirement.
One way to bridge the gap in health care coverage before Medicare is to take a part-time job that offers health insurance benefits. Many employers offer health coverage to part-time employees. This option not only helps retirees manage health care costs but also gives them an opportunity to stay active and supplement their retirement income.
Additionally, as of 2026, individuals can earn up to $24,480 per year during retirement without impacting their Social Security benefits. If retirement earnings exceed this limit, benefits may be reduced — but your clients can recoup those amounts once they reach full retirement age.

If COBRA or a part-time job with benefits isn’t available, purchasing private health insurance is another option to cover health care expenses until Medicare kicks in. The Health Insurance Marketplace, created under the Affordable Care Act (ACA), offers a variety of plans that cater to different budgets and health needs. Depending on each client’s income level, they might even qualify for a subsidy to help lower their monthly premium.
One key advantage of purchasing private insurance is the flexibility to choose a plan that best fits each person’s medical needs. Coverage can be chosen based on factors like deductibles, co-pays and provider networks. However, private insurance can be expensive, so it’s important to shop around and compare costs carefully, especially for those who have ongoing medical needs.


Annuities can be a useful tool for generating income to help cover health care expenses before Medicare. With certain annuities, clients can ensure a steady stream of income that can help them bridge the gap during their retirement years. There are several types of annuities that can meet different needs:
Retiring early is a complex decision that requires careful planning and consideration. You can provide the expertise and personalized guidance necessary to address your clients’ concerns and help ensure a smooth transition into retirement.
Having a strategy to cover health care costs before Medicare is crucial. Without one, you might feel pressured to file for Social Security benefits early just to pay for medical expenses. However, filing for Social Security benefits early reduces your monthly benefit. The longer you can delay filing, the higher your Social Security payments may be over time.
[1] "2025 EBRI/Greenwald Retirement Confidence Survey Summary Report," EBRI and Greenwald Research (April 24, 2025)