6 Essential Steps to Take Before Your 65th Birthday: Your Medicare Preparation Checklist

As your 65th birthday approaches, preparing for Medicare enrollment is one of the most important steps to ensure continuous healthcare coverage. Here’s your actionable checklist to make the transition smooth and stress-free.

1. Mark Your Medicare Initial Enrollment Period (IEP)

Your Medicare Initial Enrollment Period spans seven months – beginning three months before your birth month, including your birth month, and extending three months after. For example, if you turn 65 in July, your IEP runs from April through October. Mark these dates on your calendar and set reminders to avoid missing this crucial window.

2. Review Your Current Healthcare Needs

Take inventory of your current healthcare situation:

  • List all your prescription medications
  • Document your preferred doctors and specialists
  • Consider your typical annual healthcare expenses
  • Think about additional services you might need, like dental or vision care
  • Review any upcoming planned procedures or treatments

3. Understand Your Working Status and Current Coverage

Your employment status affects your Medicare decisions:

  • If you’re still working and covered by your employer’s plan, talk to your HR department about how your coverage works with Medicare
  • If you’re retiring, confirm your coverage end date and any retiree benefits
  • If you’re on COBRA or a marketplace plan, understand how these transition with Medicare

4. Evaluate Your Medicare Coverage Options

Research your options to make an informed decision:

  • Original Medicare (Parts A and B) with optional Medigap and Part D
  • Medicare Advantage plans (Part C) that combine all benefits – everything Original Medicare Offers plus extras like prescription drugs, dental, vision, hearing, and more.
  • Consider factors like travel plans, preferred providers, and prescription drug needs

5. Gather Required Documentation

Have these important documents ready:

  • Birth certificate or passport
  • Social Security card
  • Proof of citizenship or legal residency
  • Current health insurance information

6. Schedule a Medicare Consultation

Meet with a licensed Medicare specialist to:

  • Review your specific situation and needs
  • Understand costs and coverage options
  • Get help with enrollment paperwork
  • Learn about available resources and support

The Bottom Line

Starting your Medicare journey prepared can help you avoid costly penalties, coverage gaps, and unnecessary stress. Taking these steps before your 65th birthday will position you to make informed decisions about your healthcare coverage.

Remember, Medicare can seem complex, but you don’t have to navigate it alone. eternalHealth licensed agents are available to help you understand your options and find the right coverage for your needs.

Want to learn more about your Medicare options?

Download our comprehensive Medicare 101 Guide or schedule a free consultation with one of our licensed agents at 1 (833) 810-5377 (TTY: 711).

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eternalHealth is an HMO plan with a Medicare Contract for HMO, HMO-POS and PPO offerings. Enrollment in eternalHealth depends on contract renewal. To enroll in an eternalHealth plan you must meet certain eligibility requirements and reside in the plan’s CMS-approved service area. Benefits and cost sharing may vary by plan.


Page Last Updated On: January 20, 2025
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Tom Cunniffe

Tom Cunniffe

Director of Operations 

Tom Cunniffe comes to eternalHealth with over 20 years of healthcare operations’ experience, having held leadership positions in Call Center, Enrollment, Credentialing, UAT and Reimbursement teams. Tom has worked with Medicaid, Commercial and Medicare lines of business and has consistently built teams who are metrics driven with proven successful outcomes. Making sure our business strives for an efficient, best-in-class customer experience is at the center of Tom’s philosophy.

Tom has a bachelor’s degree from Fordham University and a master’s in business administration from University of Massachusetts at Amherst.

Tom Lawless

Tom Lawless

Chief Financial Officer

Tom Lawless has spent the past 20+ years building, sustaining, and growing new healthcare-related programs that balance fiscal responsibility & prudence with creativity & innovation, focusing on models of care that are novel, person-centered, and improve the social welfare of those who are served. He is very excited to continue doing so in his role as the Chief Financial Officer of eternalHealth.

Tom comes to eternalHealth from a not-for-profit, member-centric, health insurance cooperative. He helped the company continuously strive toward its dual goals of thriving financially, while keeping members at the very epicenter of its mission and service model. While there, Tom also spearheaded the creation of a brand new private, charitable foundation, which will be meaningfully giving back to those in need in the surrounding communities for years to come. Previously, Tom worked in the finance department of a successful hospice that provided high-quality care to persons experiencing their unique and poignant end-of-life journeys, assuring that the appropriate financing was always available. Tom’s career began as a civil servant in the Wisconsin Medicaid program, where he helped to create a program that expanded the institutional entitlement to care into home and community-based settings. Starting with only a blueprint in hand, the program now serves more than 57,000 frail elders and disabled adults and is considered a national model. Growing into a senior leadership role, Tom was a key architect of an innovative financing model, through which the public and private sectors successfully collaborated to better the lives of persons in great need.

Tom holds undergraduate and graduate degrees from the University of Chicago, with additional graduate work in economics completed at the University Wisconsin-Madison.

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