Do not wake up one morning, pour yourself a cup of coffee, crack your knuckles, and announce, “Today I’m going to fill out my Medicare application.” This is the kind of statement made by people who have not yet attempted to fill out a Medicare application. You might as well wake up and announce that before lunch you intend to learn Mandarin, replace your transmission, and negotiate peace in the Middle East. Medicare is not something you knock off between breakfast and your trip to Costco. You will not finish it in one sitting. You may not finish it in three. Accept this now and spare yourself the humiliation of watching your cheerful morning agenda disintegrate by 10:17.
Think of yourself as stepping into the batter’s box against Mariano Rivera.
For nearly two decades, major-league hitters faced Rivera knowing what was coming. He was going to throw the cutter. There was no elaborate mystery, no carnival assortment of twelve pitches requiring Sherlock Holmes to decipher the clues. Rivera stood on the mound, stared toward home plate, and essentially announced: Here comes the cutter.
Then he threw it.
And some of the finest hitters on earth swung at the thing as it darted away from the sweet spot of the bat, leaving them jammed, bewildered, or trudging back toward the dugout carrying the splintered remains of their dignity.
This brings us to The Rivera Principle: no major retirement bureaucracy can be defeated in a single sitting, even when you know approximately what is coming.
Medicare is Mariano Rivera standing sixty feet, six inches away.
You know there will be questions about health insurance. You know there will be dates. You know Social Security will somehow be involved. You know there will be usernames, passwords, authentication codes, employment records, Group Health Plans, and mysterious terminology. You have studied the scouting report. You have stretched. You have brought your reading glasses.
None of this means you are going to make contact.
The first pitch asks for a password you thought you had. Swing and miss.
The second asks for the precise date your Group Health Plan began, forcing you to wonder whether that means the year you started your job, the year your health benefits began, or the year you switched insurance carriers. Swing and miss.
The third sends you from Medicare to Social Security, causing you to wonder why you are applying for Medicare somewhere other than Medicare. Strike two.
Then Medicaid appears on a Medicare checklist, and for several bewildering seconds you wonder whether you have Medicaid, whether you were supposed to have Medicaid, or whether Medicaid has been quietly following you for years like a government surveillance van.
Foul ball.
Now HR must be contacted.
Step out of the box.
The rookie retiree interprets these interruptions as failure. He becomes agitated. He pounds the desk. He begins attacking dropdown menus with the desperate aggression of a hitter protecting the plate with two strikes. This is precisely how Mariano gets you. You become impatient. You expand the strike zone. You swing at pitches you should never have touched.
The experienced retiree develops Administrative Plate Discipline. He understands that surviving the bureaucracy requires knowing when not to swing. If you don’t know the Group Health Plan start date, don’t guess. Step out of the box. Call Benefits. If you don’t understand whether a question refers to your employment or your insurance coverage, don’t click whatever answer seems approximately correct because you would like to be finished before lunch. Put down the bat. Save the application. Walk back to the dugout.
Have lunch.
Take a nap.
Come back tomorrow.
Rivera will still be there.
This is the deeper meaning of The Rivera Principle. Your objective is not to conquer Medicare in one glorious at-bat. Your objective is to remain in the game. Foul off the difficult pitches. Take the ones you don’t understand. Get the information you need. Step out of the box when your nerves begin to fray. Return the next morning with your documents, your passwords, your HR representative’s email, and whatever remains of your self-respect.
Then dig your heels into the dirt and look toward the mound.
Rivera looks very tall from sixty feet, six inches away.
If you’re intimidated, good. You’re alive.
If you’re not intimidated, you haven’t seen the cutter yet.
Cinemorphosis 
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