Hole 01You're up
Understanding Medicare
Learn the basics — how Medicare is built and who runs it.
Caddie's tip: "A clean line beats a heroic shot."
6 min readWarm-up
The Front Nine
Learn the coursebefore you choose your shot.
Every great round starts with a calm walk up the fairway. Medicare works the same way.
We'll take you through nine clear learning holes first, then into a Back Nine built for calculators, comparisons, and confident decisions.
Round in progress
0/9 holes · ~70 min total
The Front Nine
Walk the course, hole by hole.
Read the fairway.
Take the next shot.
Take the next shot.
Hole 02
Parts A, B, C & D
Understand how each part works and what it pays for.
Caddie's tip: "Four routes, one system."
8 min readFoundational
Hole 03
Turning 65
Know your enrollment timeline and the moments that matter most.
Caddie's tip: "Timing matters more than distance."
7 min readEasy
Hole 04
Enrollment Periods
IEP, AEP, MA-OEP and SEPs — the windows you can't miss.
Caddie's tip: "Choose the right path before the course narrows."
9 min readCore
Hole 05
Medicare Costs
Premiums, deductibles, coinsurance, IRMAA and MOOP.
Caddie's tip: "Respect the hazard before you attack the pin."
10 min readCore
Hole 06
Original Medicare vs Advantage
Two valid routes — both can be the right play.
Caddie's tip: "Protection changes the shot."
9 min readCore
Hole 07
Doctors, Pharmacies & Networks
Learn what to check before you commit to a plan.
Caddie's tip: "Start from the tee box that fits your position."
7 min readApplied
Hole 08
Comparing Advantage Plans
Benefits, costs and tradeoffs — read the entire hole.
Caddie's tip: "The safe route is still a smart route."
8 min readApplied
Hole 09
Choosing Your Plan
Bring it together and enroll with confidence.
Caddie's tip: "See the clubhouse. Finish with conviction."
6 min readApplied
The Turn
Welcome to the Back Nine.You've finished the Front Nine.
You've built the foundation most people never get. The Back Nine is where learning becomes decision — calculators, comparisons, and the final green.
The Back Nine
Apply what you've learned.
Nine more holes — calculators, comparisons and conversations — all the way to the 18th green.
Hole 10
Calculators
Run the numbers on IRMAA, penalties and enrollment.
"Distance matters. Measure first."
Play this hole →
Hole 11
Glossary
Every Medicare term, in plain English.
"Know the language of the course."
Play this hole →
Hole 12
Questions
The questions people actually ask, answered directly.
"Work the practice green before the round."
Play this hole →
Hole 13
Compare Plans
Side-by-side plan comparisons for your zip.
"Read both fairways before choosing one."
Play this hole →
Hole 14
Search the Encyclopedia
Search every Medicare term in the plain-English encyclopedia.
"Sometimes the right club comes from asking the right question."
Play this hole →
Hole 15
Personas
See how people like you approached the same decision.
"Every golfer sees a different opening."
Play this hole →
Hole 16
News
What's changing in Medicare — and what it means.
"Course conditions change every season."
Play this hole →
Hole 17
Meet Your Caddies
The people behind Medicare Caddies.
"A great round starts with trusted guidance."
Play this hole →
Hole 18 · The Final Green
Compare Medicare Advantage plans.
Bring everything you've learned to the final green. Compare real plans in your zip and enroll with confidence when you're ready.
Caddie: "You've walked the whole course. Time to finish the round well."
Sink the putt →Your Caddie for the Long Game
We're here for more than enrollment.We're here for the entire round.
Most Medicare websites help you choose a plan. Medicare Caddies stays with you after you've enrolled.
Whether you enroll online or with one of our licensed insurance agents, you'll always know who to reach out to when Medicare questions come up. When possible, you'll work with the same Medicare Caddie who already knows your situation — no call center, no starting over, no explaining your story to someone new every time.
- Understanding your plan
- Annual Election Period reviews
- Moving to another state
- Doctor network questions