In this episode of Retire With Style, Wade Pfau and Alex Murguia walk through what actually happens when you enroll in Medicare and where people tend to make costly mistakes. They break down the enrollment timeline, clarify how Medicare interacts with Social Security, and explain why failing to enroll can leave you unexpectedly exposed to major healthcare costs. The conversation also explores how Medicare decisions fit into broader retirement planning, including healthcare cost estimates, risk preferences, and the role of Health Savings Accounts (HSAs) in preparing for future expenses. Takeaways Medicare enrollment is not automatic if you delay Social Security, you must sign up yourself. At age 65, Medicare typically becomes your primary insurance, and other coverage may not be paid without it. Not enrolling in Medicare can leave you exposed to major out-of-pocket healthcare costs. Many types of coverage (COBRA, ACA plans, retiree insurance) do not count as primary after 65. A typical couple may need around $375,000 for healthcare in retirement (excluding long-term care). Medicare choices reflect your risk preference: pay more upfront for predictability or less with more uncertainty. Chapters 00:00 Introduction to Medicare and Health Insurance 09:39 Understanding the Medicare Enrollment Process 18:50 Financial Planning for Healthcare Costs Links 📣 Want a heads up for the next Retirement Income Challenge? Join the waitlist and be the first to know when registration opens for this FREE 4-day event hosted by Retirement Researcher. Visit retirewithstyle.com/RIC to learn more and save your spot. 📘 New Release: The Retirement Planning Guidebook (3rd Edition) Wade Pfau’s must-read Retirement Planning Guidebook just got even better. The 3rd Edition is now available and packed with the latest updates to help you design your retirement strategy with confidence. Grab your copy on Amazon or your favorite book retailer: https://books2read.com/Retirement This episode is sponsored by Retirement Researcher https://retirementresearcher.com/. Download their free eBook, 8 Tips to Becoming A Retirement Income Investor at retirementresearcher.com/8tips