Brian Dress, CFADirector of Research, Investment Advisor, Left Brain Wealth Management, LLC · Wealth Strategy for Corporate Executives & High-Net-Worth Investors | Concentrated Stock & Equity Compensation Planning | Director of Research | CFA | Left Brain Wealth Management

The Healthcare Bill Nobody Budgets For in Early Retirement

6 Oct 2026 · 1 min

Watch on YouTube

1:15

In this segment of the YouTube video, Brian Dress (Speaker A) and a co‑host (Speaker B) discuss the often‑overlooked "Medicare gap" that early retirees face when they leave the workforce before age 65. They explain that retirees who stop working at 50 must fund 15 years of private health insurance, which can cost roughly $20,000–$30,000 per year. The conversation highlights recent 20% annual premium hikes, showing how these increases can compound to a total outlay of about $500,000 over the 15‑year period. They also note that the exact cost varies widely based on geography, family size, income, and coverage choices. The key takeaway is that failing to explicitly model this healthcare expense can create a substantial shortfall in an early‑retirement financial plan.

If you retire at 50, you've got one expense staring you right in the face that someone retiring at 65 largely doesn't. You've got 15 years until Medicare. Nolan, as a rough planning baseline, if we're thinking $20,000 to $30,000 a year for healthcare, how should someone actually model that in their plans?
You definitely want to model it in there, and you want to increase whatever your income needs are by that healthcare number. But it gets scary, Brian, as well. Think about this year. We had, on average, 20% increase in healthcare premiums. I mean, that's a scary increase to put into a retirement income model for healthcare costs. So the numbers are high, and I'm gonna imagine over a course of 15 years before Medicaid kicks in or Medicare kicks in, you might be looking at $500,000 of cost with potentially substantial annual increases.
And that number can move quite a bit depending on your geography, your family size, your income, and your coverage options as well, right?
Absolutely. It all matters. So you really want Look at this number carefully.
So that exact medical expense number is personal, but pretending that healthcare gap isn't there can blow a pretty huge hole in an early retirement plan.