Journey/Pre-Retirement/Bridging the Healthcare Gap
Pre-Retirement · Ages 50–64 · 6 min

Bridging the Healthcare Gap

Medicare starts at 65. If you retire before that, healthcare is your largest expense — and your largest risk. One serious illness before Medicare can devastate a retirement plan.

Key Decisions at This Stage
Plan for healthcare costs from retirement date to 65 (if retiring early).
Decide between marketplace insurance, COBRA, or spouse coverage for the gap.
Maximize HSA contributions while eligible — it's the best retirement health fund.
HSA triple advantage
Health Savings Accounts offer: (1) tax deduction on contributions, (2) tax-free growth, (3) tax-free withdrawals for healthcare. After 65, withdrawals for any purpose are taxed but not penalized — functionally a second IRA.
Medicare gap
The period between early retirement and Medicare eligibility at 65. Average cost: $700–$1,500/month per person in marketplace insurance. A critical gap in most retirement projections.
Medigap / Medicare Supplement
Private insurance that covers costs Medicare doesn't (copays, deductibles, foreign travel). Premiums vary by plan and age. Buying during initial enrollment avoids health underwriting.
1
Maximize HSA contributions every year you're eligible.
2
Get a marketplace insurance quote to understand the real cost of early retirement.
3
Research Medicare supplement options 2 years before turning 65.

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