Turning 65
Turning 65 in California: your Medicare checklist
Medicare has a handful of deadlines that are easy to miss and expensive to miss. This is the order I walk my own clients through, starting about six months before their 65th birthday.
Six months before your birthday
- If you contribute to a health savings account, stop now. This is the single most common expensive mistake I see. When you enroll in Medicare Part A, coverage can be backdated up to six months, and you are not allowed to contribute to an HSA for any month you have Medicare. Contributions made during a backdated period can trigger tax penalties. If you plan to enroll at 65, stop HSA contributions six months before.
- Find out what happens to your current coverage. If you're working, ask your HR department in writing whether your plan is considered creditable coverage and whether it becomes secondary to Medicare at 65. Small employers in particular often have rules that surprise people.
- Write down your doctors and prescriptions. Every name, every medication, every dosage. These two lists drive the entire decision, and gathering them early makes everything after this easier.
Three months before your birthday
- Your Initial Enrollment Period opens. It runs seven months total: the three months before your birthday month, your birthday month, and the three months after. Enrolling in these first three months means coverage starts the first day of your birthday month, with no gap.
- Enroll in Part A and Part B through Social Security at ssa.gov, unless you're staying on employer coverage. If you already receive Social Security benefits, you're typically enrolled automatically and your card arrives in the mail.
- Decide which path you're taking — a Medicare Advantage plan, or Original Medicare plus a Medicare Supplement and a drug plan. This is the fork in the road, and it's the conversation worth having with someone who will explain both honestly.
Your birthday month
- Your six-month Medigap window opens the month your Part B starts. During this one-time window, Medicare Supplement companies must accept you regardless of your health history. Outside it, they can ask health questions and decline you. This is the most important deadline in Medicare that almost nobody tells you about.
- Enroll in drug coverage, either built into a Medicare Advantage plan or as a stand-alone Part D plan. Skipping it when you take no medications is a common and costly decision — see why the Part D penalty matters.
Every year after
- Review your coverage each fall. The Annual Enrollment Period runs October 15 through December 7 for coverage starting January 1. Plans change their networks, drug lists, and costs every year, and so does your health.
- If you have a Medicare Supplement, watch your birthday. California gives Medigap policyholders an annual window to switch plans without health questions. See the California birthday rule.
The one deadline to circle: your six-month Medigap open enrollment window, which starts when your Part B begins. Miss it and a Medicare Supplement can require you to pass health underwriting for the rest of your life.
New to Medicare generally? Start with the plain-English guide to how Medicare works. Want to talk about your own situation? A consultation is free and there's no obligation.
Let's talk
Questions about your own situation?
Call or text Justin
(916) 343-8517Monday – Friday, 9am – 6pm
Evenings and weekends by appointment
When we talk, have handy:
- Your red, white, and blue Medicare card (if you have one)
- A list of your doctors and any specialists you see
- A list of your prescription medications and dosages
- Your current plan information, if you're already enrolled
Serving Placer, Sacramento, Nevada & Yuba counties