Medicare
Medicare Basics
The whole system on one page, in the order the decisions actually happen.

Medicare is not one decision. It is a sequence of them, and they arrive on a calendar set by your birthday rather than by when you feel ready.
The mail starts arriving about six months before your birthday. Almost none of it explains the order these decisions have to be made in.
This page walks the sequence in order: when your window opens, which of the two coverage paths you are choosing between, how prescriptions are handled, and what the whole thing costs. Each step links to a page that goes deeper.
How the pieces stack
Everyone starts with the same two parts. The choice comes after.
Read top to bottom. The prescription decision depends on the one above it, which is why taking them in the wrong order causes most of the trouble.
This is probably you if…
- You are turning 65 within the next year
- You are past 65 and about to leave employer coverage
- You are helping a parent who is already enrolled and unhappy
- You have a plan already and have not had it reviewed since you chose it
What this includes
The scope of work, in plain terms.
First, the calendar
Which window you are in decides what you are allowed to do. Some of them carry penalties that never come off.
Then, the fork
Original Medicare with a supplement, or Medicare Advantage. Two different philosophies, and the first choice is stickier than it looks.
Then, prescriptions
Part D is its own decision with its own penalty, and it works differently depending on which path you took at the fork.
Last, the cost
Premiums, deductibles, and an income-tested surcharge that keys off a tax return you filed two years ago.
Turning 65, or leaving employer coverage? Start with a conversation.
Alan Trotsky
Alan Trotsky has been a financial professional for over 40 years. Prior to entering the insurance industry, Alan worked as a CPA serving clients with tax and financial planning. He also has experience providing consulting services to numerous businesses in various industries.
What to expect
- 01 A conversation What coverage you have now, whether you are still working, and when your window opens. Nothing to prepare and nothing to sign.
- 02 Your doctors and your prescriptions We check your prescriptions and your doctors against the plans available where you live. This is the step most people skip and most regret skipping.
- 03 Options side by side You see the real trade-offs between the paths open to you, including the ones that are hard to reverse later. Then you decide.
- 04 Every fall, we look again Plans change their formularies and networks each year. We review yours before the December deadline, whether or not anything changes.
Talk it through with Alan
True wealth is more than money.
Start with a conversation. No cost, no pressure, no obligation to continue.
