Medicare Enrollment Problems

Yikes, readers of this Substack know that retiring around the time of your 65th birthday can lead to strange outcomes.

  • You don’t want a lapse in coverage, you may have a health situation that requires immediate / constant attention.

  • You don’t want to be double-covered, especially if you would face IRMAA. We are talking about $170.10 + possible Part B and Part D IRMAA. For some this may seem ‘worth it,’ but not for others.

  • You don’t want to face late enrollment penalties

There is the BENES Act, which takes effect in 2023, but for now, this problem continues to baffle applicants (you) and the SSA, which is inconsistently applying the rules.

Not The First Time, Won’t Be The Last

Most of the time, I am not sympathetic to those that start their protests with the sentence “It’s not fair that…” Don’t get me started. These rules are in writing, they are known, there is a book (ahem, available for pre-order on, YouTube Channel to explain financial concepts, this free newsletter, subscription service for sensitive information, professional services, all set up to explain why my definition of “fair” doesn’t matter, it is a question of correctly understanding the rules.

However, when you follow the rules correctly, and then a government employee wrongly informs you, or there are undue delays at the government? That is entirely different. The idea that you can do these by yourself?

  • Detect the error

  • Know how to address the error

  • Avoid the error by pre-emptively acting early and correctly

Nah. It’s just a sample of over 100 videos. Don’t forget to subscribe.