09/02/2026
A lot of clients we help have the financial means to retire early, sometimes in their late 50s or early 60s.
Executives. Doctors. Professors. Business owners.
They’ve saved and planned and are ready for their next chapter.
But one decision can still keep them up at night: health insurance.
If you retire before age 65, you may have several years to bridge before Medicare begins. And how you cover that gap can have impact on your retirement income and tax strategy.
There are three common ways to bridge the gap:
- COBRA coverage through your former employer
- Health insurance through the ACA Marketplace
- Coverage through a spouse’s employer-sponsored plan
The right option depends on more than the monthly premium. Your income, taxable withdrawals, potential ACA subsidies, healthcare needs, and retirement timeline can all factor into the decision.
Can you stop working? Yes. But you also need to assess how health insurance fits into your overall retirement plan.Wondering how the Medicare gap fits into your plan?
Book a free 15-minute call and we'll walk through it together: https://go.sjboylewealthplanning.com/consult-schedule