Medicare is complicated.
I make it simple.

Your Initial Enrollment Period is a 7-month window: the three months before the month you turn 65, your birthday month, and the three months after. Enrolling on time matters — delaying Part B or drug coverage without other qualifying coverage can mean permanent late-enrollment penalties. If you're still working and covered by an employer plan, you may be able to delay without penalty, but the rules depend on your situation.

They are two very different approaches. Medicare Advantage (Part C) replaces how you receive Original Medicare: plans are offered by private carriers, usually have networks of doctors and hospitals, often include drug coverage and extras like dental or vision, and typically have low monthly premiums with pay-as-you-go costs. A Medicare Supplement (Medigap) works alongside Original Medicare: you can see any doctor in the country who accepts Medicare, your out-of-pocket costs are more predictable, and premiums are higher — plus you add a separate Part D drug plan. Neither is universally better; the right fit depends on your doctors, prescriptions, budget, and how you like to manage risk.

Usually, yes — and here's why: if you go without creditable drug coverage for 63 or more days after your enrollment window, Medicare adds a permanent late-enrollment penalty to your premium when you do eventually enroll. Many of my clients who take no medications enroll in the lowest-premium Part D plan available simply to avoid that lifelong penalty and to be covered if a prescription need appears suddenly.

You'll never receive a bill from me. Like nearly all Medicare agents, I'm compensated by the insurance carriers when I help someone enroll, and those rates are set so that your premium is exactly the same whether you enroll through me, directly with the carrier, or through Medicare.gov. The difference is that you get an advisor who works with multiple top-rated carriers, explains the trade-offs in plain English, and picks up the phone after you've enrolled.