Episode Overview

Podcast: Ready For Retirement
Episode: “The Biggest Retirement Lie: ‘I Can’t Retire Until Medicare’”
Host: James Conole, CFP®
Date: February 15, 2026

In this episode, James Conole tackles a deeply entrenched belief among pre-retirees: the notion that you “can’t retire until Medicare” at 65 due to employer-sponsored health insurance concerns. James aims to debunk this myth by breaking down real-life examples, sharing actionable strategies to manage healthcare expenses pre-Medicare, and encouraging listeners to consider early retirement if they’re otherwise financially ready. His central message is clear—waiting for Medicare could be costing you the most vibrant years of your retirement, and it doesn’t have to be that way.

Key Discussion Points & Insights

1. The "Medicare Lock" Myth

• Common Belief: Many people, even with adequate assets, stay in jobs longer than necessary because they fear losing employer health insurance before Medicare eligibility.
• James’s Take: “On the surface, it sounds responsible, but here's the uncomfortable truth. That is the single biggest lie keeping you at a job that you no longer need.” (00:13)
• Clarification: Health insurance is crucial, but it does not need to tie you to employment until 65.

2. Real-Life Case Study: Carl and Sally

James presents a detailed case study to illustrate his argument.

• Profile:

  • Ages: Carl (58), Sally (59)
  • Net Worth: Substantial ($875k in IRAs, $1.4m joint account, $625k property, HSA)
  • Recent Downsizing: Led to more liquid assets
  • Goals: $7,000/month living expenses + $30k/year travel

• The Dilemma: “They want to retire now. But much like you, their concern is, what are we going to do for health insurance?” (02:52)

• Scenario 1: Work until 65, accumulate ~$5m, retire with assets still growing.

• Scenario 2: Retire now; concern is health insurance pre-Medicare.

3. Modeling Early Retirement

• Financial Projections: Even if Carl and Sally retire 6-7 years early, their probability of financial success remains extremely high (99% before factoring in health insurance, 98% after incorporating an assumed $40,000/year for insurance premiums).
• Key Insight: “I have seen people with millions...who are still working because of health insurance…Treat health insurance properly. Treat it like an expense.” (08:04)
• Real Cost: Delaying retirement for insurance can mean giving up “six to seven years of freedom…when they're at their youngest, the most vital, the most energized ages.” (10:06)

4. Practical Options for Pre-65 Health Coverage

James outlines four primary ways to bridge the gap between workplace health coverage and Medicare:

1. COBRA

   • Allows continued coverage of employer plan (at full cost to employee).
   • Useful for those who want consistency.
   • (11:01)

2. ACA (Affordable Care Act) Marketplace Plans

   • Dependent on state, providers, and coverage needs.
   • Health insurance experts can help navigate choices, considering income and tax implications.
   • (11:45)

3. Private Plans & Cost-Sharing Networks

   • Alternative solutions, not technically insurance in all cases (e.g., health sharing ministries).
   • Can work for some situations.
   • (12:23)

4. Part-Time Work with Benefits

   • Consider reducing to part-time or transitioning to a different, lower stress job that provides coverage.
   • “Maybe it pays a whole heck of a lot less money, but you maintain your coverage.” (13:03)
   • Flexibility to “fully do what you want to do.”

5. The Real Cost of Waiting

• Core Message: The cost of waiting for Medicare isn't about the insurance premiums—it's about missing out on health, energy, and freedom in the pre-65 years.
• “If you have a plan. If you have a strategy, health insurance simply becomes another line item in that plan that allows you to live the life you want to live.” (14:12)

Notable Quotes & Memorable Moments

• “Fire your employer, meaning you need to understand what benefits do you get from your employer and how do you shift those to getting them on your own…” – James Conole (07:49)
• “Treat health insurance properly. Treat it like an expense, like you would a vacation, like you would groceries, like you would gas and fuel. Don't treat it as this thing that you have to get until Medicare age to start using.” – James (08:32)
• “The real cost, based upon the way they're planning for it, probably based upon the way you are planning for it, is six to seven years of freedom.” – James (10:01)
• “Don't let health insurance be the blocker between you and living the life you want to live.” – James (13:45)

Timestamps for Key Segments

• 00:13 – Introduction to the “Biggest Retirement Lie”
• 01:35 – Setup of Carl and Sally case study
• 05:03 – Difference between working to 65 vs. retiring early; potential growth of assets
• 07:49 – The true “cost” of insurance: time, not just money
• 09:43 – Health insurance as an expense, not a gatekeeper
• 11:01 – Health coverage options: COBRA, ACA, private plans
• 13:03 – Consideration of part-time work with benefits
• 14:12 – Summarizing the real cost of waiting: missed energy and freedom

Conclusion

James Conole’s episode disrupts the conventional wisdom that employer-sponsored health insurance is an immovable barrier to early retirement. Through real-life examples, practical solutions, and motivational coaching, he reframes health insurance as a manageable, albeit significant, expense—and not a retirement dealbreaker. For listeners feeling “locked in,” this episode provides both reassurance and a roadmap for reclaiming valuable years before 65.

Summary prepared for Ready For Retirement podcast listeners.