Turning 65: a checklist that starts six months out

Turning 65 arrives with a pile of mail and a deadline you did not set. Most of the mail is advertising. A small number of decisions genuinely matter, and two of them are difficult to undo. This is the order to take them in.

Six months out: work out whether you even enroll yet

The first question is not which plan. It is whether you should enroll in Part B now at all. If you are still working and covered by an employer plan, the answer depends on the size of the employer and whether the coverage counts as creditable.

Get this wrong in one direction and you pay for coverage you do not need. Get it wrong in the other and you take a permanent Part B penalty. It is a five-minute conversation that is worth having with someone who has had it a few hundred times.

• Confirm whether you are automatically enrolled — if you already draw Social Security, you generally are
• Ask your HR or benefits administrator, in writing, whether your drug coverage is creditable
• Find your Medicare number, or start the enrollment application through Social Security
• Write down your doctors, your specialists and your prescriptions with dosages — this list drives every later decision

Three months out: the decision that is hardest to reverse

This is where you choose between Medicare Advantage and a Medicare Supplement. Both are legitimate. They suit different people, and the honest comparison depends on your doctors, your prescriptions and how much unpredictability you want to carry.

What makes the timing matter is that your six-month Medigap Open Enrollment window is running. During it you can buy any Medigap plan in Utah regardless of your health. Afterwards, in most situations, a carrier can ask health questions and decline you. So this is the moment when both doors are genuinely open.

Three months out: sort out prescriptions properly

Whichever route you choose, drug coverage is its own decision, and it is the one most often made badly. Do not pick a Part D plan on its premium.

List each medication with dosage, check which tier each plan puts it on, and price it at the pharmacies you would actually use. Compare total expected yearly cost — premium plus deductible plus what you pay at the counter. Two plans with the same premium can differ by a four-figure amount for the same person.

One month out: confirm the details before anything starts

• Confirm your coverage start date and that your Medicare card has arrived
• Re-check every doctor against the plan network — networks change, and you want the version that applies on day one
• Confirm your pharmacy is in the plan's preferred network, which is where the better pricing usually sits
• Decide whether you want a standalone dental, vision and hearing policy alongside your Medicare coverage
• Save your agent's direct number somewhere you will find it in a hurry

Your first year: the part people are not warned about

Something will not go the way you expect. A claim will process oddly, a pharmacy will quote a price that does not match what you were told, or a specialist's office will say something contradictory about your coverage. This is normal and usually fixable.

What matters is having someone to call who knows your plan and will actually deal with it. If your enrollment came through a call center, you will be explaining your situation from scratch to whoever answers. That difference is most of why people work with a local independent agent.

Every year after: do not let it roll over unexamined

Your plan sends an Annual Notice of Change each September describing exactly what will be different in January — network, formulary, copays, other benefits. Read it, or have someone read it with you.

Then, during the Annual Enrollment Period from 15 October to 7 December, review whether the plan still fits. Most years nothing needs to change. The years when something does are exactly the years you would not have noticed on your own.

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The bottom line

Start six months out, get the Part B timing right, and treat the Advantage-versus-supplement decision as the consequential one it is. If you would rather not do it alone, that is what Sarah is for — and the conversation costs you nothing.