Mistake 1: Missing your enrollment window
Your Initial Enrollment Period is seven months built around your 65th birthday, and it does not send reminders. People assume someone will tell them when to act. Nobody does. Miss the window without qualifying coverage and you face gaps in coverage and penalties that can follow you for life.
The fix: Put your window on the calendar the day you turn 64. Better yet, have a licensed agent map your exact dates in a ten minute call, free, a year ahead.
Mistake 2: Assuming COBRA or retiree coverage protects you
COBRA looks like employer coverage and feels like employer coverage, but Medicare does not treat it as employer coverage. People ride COBRA past 65, skip enrolling, and discover the clock on their penalty free window started the day they left work, not the day COBRA ends.
The fix: The moment retirement enters the conversation, before you sign anything, confirm how your situation interacts with Medicare's timing rules. Ten minutes now beats a lifelong penalty later.
Mistake 3: Choosing a plan without checking your doctors
Plan advertisements show benefits. They do not show whether your cardiologist is in the network. Every January we meet people who enrolled from a TV ad or a phone call and learned in the exam room that their doctor of fifteen years is now out of network.
The fix: Never enroll in any plan until your actual doctor list and your actual medication list have been checked against it. We do this check for every client, before enrollment, every time.
Mistake 4: Skipping drug coverage because you take no medications
It feels logical: no prescriptions, no drug plan. But Medicare penalizes going without drug coverage, and the penalty grows for every month you wait and then stays with you permanently once you do enroll. Health can change faster than enrollment windows open.
The fix: Even if you take nothing today, understand what going without creditable drug coverage costs you long term before you decide. Often a modest plan now is the cheaper lifetime decision.
Mistake 5: Buying from a stranger on the phone with no local person to call afterward
Enrollment season floods every mailbox and phone in Los Angeles with offers. Many are legitimate. But when February arrives and a bill looks wrong or a claim gets denied, the call center that enrolled you is gone, and you are alone with a phone tree.
The fix: Enroll through someone local and licensed who will still answer in February, in May, and next year. The plan costs the same either way. The difference is who stands behind it.