What Creatives Need to Know About Signing Up for Medicare at 65

Mark Stern |

Turning 65 is a milestone for anyone, but for creatives—artists, writers, designers, and other self-employed professionals—it brings unique questions about health insurance. Medicare, the federal health insurance program for people 65 and older, can seem confusing, especially if your career path hasn’t followed a traditional employer-based route. Here’s what you need to know to make the transition smooth and avoid costly mistakes.

1. Eligibility and Timing: Don’t Miss Your Window

  • Eligibility: Most U.S. citizens and legal residents who have lived in the country for at least five years can sign up for Medicare at 65.
  • Initial Enrollment Period (IEP): This is a 7-month window—starting 3 months before your 65th birthday, the month you turn 65, and ending 3 months afterMissing this period can lead to penalties and gaps in coverage. [2]

Key point

If you miss your 7-month Initial Enrollment Period, you may have to wait to sign up and pay a monthly late enrollment penalty for as long as you have Part B coverage. The penalty goes up the longer you wait. [2]

2. How to Sign Up: Automatic vs. Manual Enrollment

  • Automatic Enrollment: If you’re already receiving Social Security or Railroad Retirement Board benefits before turning 65, you’ll be enrolled automatically in Medicare Part A and Part B [3][4].
  • Manual Enrollment: If you’re not yet receiving Social Security, you must actively sign up for Medicare. You can do this online, by phone, or at your local Social Security office[3][4].

3. What Does Medicare Cover?

 

Part A

Hospital stays, skilled nursing, hospice, home health care [1][4]

Part B

Doctor visits, outpatient care, preventive services [1][4]

Part C

Medicare Advantage -private plans combining A & B, marketed heavily as having extra benefits but see my note below [4][7]

Part D

Prescription drug coverage[4]

  • Original Medicare (Parts A & B) covers most hospital and medical services, but not everything. Many creatives choose to add Part D for prescriptions or a Medigap policy for extra coverage [1][4].
  • Medicare Advantage (Part C) should be avoided in my opinion based on all reliable reports that I have read. Some say that the law that created it was a massive giveaway to the for-profit health insurance industry. Medicare Advantage increasingly appears to be a colossal failure and after generating mega-profits for the health insurance industry, the losses are piling up while seniors are encountering scandalous levels of denial of service. [7]

4. Special Considerations for Creatives and Self-Employed

  • No Employer Plan? If you’re self-employed or freelance, you likely don’t have employer health insurance. Medicare will become your primary coverage at 65.
  • Still Working? If you have coverage through a spouse’s employer or a group plan, you may be able to delay Part B without penalty. However, COBRA or retiree coverage does not count as active employer coverage, so you must enroll in Medicare on time to avoid penalties [5]
  • Tax Implications: Self-employed creatives may have deducted health insurance premiums in the past. With Medicare, premium deductions can still apply, but consult a tax professional for specifics [6].

5. What Happens If You Miss the Deadline?

  • Late Enrollment Penalties: If you don’t sign up during your IEP and don’t have qualifying coverage, you’ll pay higher premiums for Part B (and possibly Part D) for life [2].
  • Special Enrollment Periods: If you’re covered by an employer plan (yours or your spouse’s), you can enroll in Medicare later without penalty, but you must do so within 8 months of losing that coverage [5].

6. How Much Will It Cost?

  • Part A: Usually free if you or your spouse paid Medicare taxes for at least 10 years.
  • Part B: Has a monthly premium, which can vary based on your income [4].
  • Part D and Medigap: Additional premiums apply.

7. Getting Help

  • Official Resources: Visit Medicare.gov or call 1-800-MEDICARE for guidance.
  • Local Assistance: State Health Insurance Assistance Programs (SHIPs) offer free counseling.

Final Thoughts:


Creatives turning 65 should mark their calendars for their Initial Enrollment Period, understand their coverage options, and seek advice if they’re still working or have unique circumstances. Missing deadlines can be costly, but with a little planning, Medicare can provide a solid health insurance foundation for your next creative chapter


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References:

  1. https://www.medicare.org/articles/what-medicare-benefits-can-i-get-at-65/
  2. https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start
  3. https://www.medicare.gov/basics/get-started-with-medicare
  4. https://www.usa.gov/medicare
  5. https://www.fidelity.com/learning-center/personal-finance/retirement/medicare-and-working-past-65
  6. https://www.coveringcfl.net/the-ultimate-guide-to-health-insurance-for-artists/
  7. https://cepr.net/publications/medicare-advantage-myth-busting/