Retire Today

Master Medicare with These 6 Simple Steps


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Learn how to master Medicare and get the coverage you need at the best rate available.

Too many people are guilty of making Medicare either too complicated or too simple. How do you find that middle ground? Last week’s episode of “Retirement Revealed” with Melinda Caughill was an extensive deep-dive into Medicare that provided impactful information related to making your Medicare decision. This week I’m breaking down the simple 6 step process to mastering Medicare based on Diane Omdahl’s book “Medicare for You”.

1. Timing Your Medicare Enrollment

One common misconception is that you must enroll in Medicare at age 65. While many people do, it’s not a one-size-fits-all rule. If you’re already receiving Social Security benefits, your enrollment is automatic. However, if you’re not, you’ll need to sign up manually. Consider your employment status and current health coverage. Many people are unaware that if you’ve got coverage through a group health plan from a current employer (either yours or your spouse’s), you might be able to delay your Medicare enrollment without penalty.

2. Choosing Your Medicare Path

Deciding between Original Medicare and Medicare Advantage is a crucial step. Original Medicare includes Part A (hospital insurance) and Part B (medical insurance) and gives you the option to add Part D for prescription drugs and Medigap policies for additional coverage. Medicare Advantage, on the other hand, bundles these services and often includes additional benefits. Consider your healthcare needs, budget, and flexibility preferences when making this choice. Remember, transitioning between these options down the line can be challenging, so weigh your long-term needs carefully.

3. Selecting the Right Plan

Once you’ve chosen your path, it’s time to select a plan. This often involves sifting through numerous brochures or consulting with an insurance agent. I suggest finding an independent brokerage insurance agent, preferably one who represents multiple companies to get a comprehensive view. In some regions, you might find both Medigap and Advantage plans offered by various companies. Your choice should align with your healthcare providers, drug prescriptions, and budget. Be cautious of biases; sometimes, agents might suggest plans with higher commissions.

4. Enrolling in Medicare

Enroll in Medicare well ahead of your birthday month to ensure you’re covered when you turn 65. The enrollment process is straightforward and can be done quickly online at ssa.gov. Registering early avoids gaps in coverage and ensures you’re ready to select your preferred plan when needed. Remember, enrolling in Medicare is the first step before selecting any specific Medigap, Advantage, or Part D plan, as you’ll need your Medicare number to proceed with these.

5. Enroll in a Plan

Take advantage of tools available like the Medicare.gov Plan Finder to assess your options. This resource helps you compare plans based on coverage, cost, and your healthcare needs. If this feels overwhelming, Melinda Caughill’s platform, HeyMOE.com, offers personalized assistance in finding the most cost-effective drug coverage plans. Keep an open mind and explore all available resources to make informed decisions about your Medicare options.

6. Annual Coverage Review

Medicare isn’t a one-time decision—it requires an annual review. Plans change, as do your health needs, so reassess your Medicare coverage every year. Changes in network providers, drug formulary updates, or shifts in your medical needs necessitate a yearly evaluation to ensure you’re still on the best plan. Use tools like the Medicare.gov Plan Finder for yearly assessments, or consult services like HeyMOE.com to avoid missing critical updates or cost-effectiveness opportunities.

By following these six steps, you can manage your Medicare choices with confidence, ensuring that your healthcare in retirement aligns with your personal needs and financial strategies. 

Don’t forget to leave a rating for the “Retirement Revealed” podcast if you’ve been enjoying these episodes!

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Apple Podcasts: https://podcasts.apple.com/us/podcast/retirement-revealed/id1488769337

Spotify Podcasts: https://bit.ly/RetirementRevealedSpotify 

Additional Links:

  • www.medicare.gov – Medicare Open Enrollment
  • https://www.medicare.gov/plan-compare/ – Medicare Plan Finder
  • www.heymoe.com – Annual Open Enrollment Plan Reminder & Evaluator, Melinda Caughill
  • “Medicare for You” by Diane Omdahl: https://www.i65.com/store/medicare-for-you-book 
  • Connect With Jeremy Keil:

    • Keil Financial Partners
    • LinkedIn: Jeremy Keil
    • Facebook: Jeremy Keil
    • LinkedIn: Keil Financial Partners
    • YouTube: Retirement Revealed
    • Book an Intro Call with Jeremy’s Team
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      Videos/Podcasts/Blogs (media) published prior to June 30, 2025, were recorded and approved while the advisor was affiliated with Thrivent Advisor Network. These media reflect the advisor’s views and interpretations at that time. The information and disclosures contained in those media were believed to be accurate and complete as of the date of recording, but may not reflect current market conditions or Alongside, LLC, policies.

      All content is provided for educational purposes only and does not constitute personalized investment advice. Read below for current disclosures and potential conflicts of interest.

      This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.

      The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past Performance is no guarantee of future results.

      Legal & Tax Disclosure

      Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.

      Advisor Disclosures

      Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.

      Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.

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