When I first dipped my toes into the Medicare waters, I half expected a lifeguard to blow the whistle and shout, “Too confusing—get out!” I mean, who knew that turning 65 came with an avalanche of paperwork, choices, deadlines, and acronyms? But I promise, choosing a Medicare plan doesn’t have to feel like learning a second language—or solving a Rubik’s cube while blindfolded. If I can figure out how to choose a Medicare Plan, so can you. So let me walk you through how I tackled it, step by step, with a little bit of sanity and a lot of coffee.

First off, let me say this: Medicare is not one-size-fits-all. And that’s actually a good thing. Just like retirement itself, your health care needs are personal. Maybe you’ve got a clean bill of health and only visit the doctor for your yearly checkup—or maybe your calendar looks like a medical road trip, complete with specialists, prescriptions, and follow-ups. Whatever your situation, there’s a Medicare plan combination out there that can work for you.

I started by figuring out the basics—what each part of Medicare actually does. Medicare Part A is hospital insurance. It generally covers inpatient stays, hospice, and some home health care. Most folks get it for free, assuming they or their spouse paid into Medicare for at least 10 years. Part B is medical insurance. That covers doctor visits, preventive services, outpatient care—basically, the stuff you use more often. It comes with a monthly premium, and yes, it goes up a bit if your income is higher.

Now, once I had my Part A and B lined up, I had to choose: Do I want to keep Original Medicare and add a Medigap supplement and a Part D plan for prescriptions, or do I want to go the all-in-one route with a Medicare Advantage Plan (Part C)? Cue dramatic music.

Original Medicare is like à la carte dining, you pick what you want, and you pay for it individually. If you go this route, you can see almost any doctor who takes Medicare, anywhere in the country. That flexibility was tempting. But without a Medigap plan, you’re responsible for 20% of medical costs, and there’s no out-of-pocket limit. That made me nervous. I’ve seen enough hospital bills in my day to know that 20% of “a lot” is still “a whole lot.”

On the other hand, Medicare Advantage is more like a buffet. These plans are offered by private insurers approved by Medicare, and they bundle hospital, doctor, and often drug coverage into one tidy package. Some even throw in extras like dental, vision, hearing aids, or gym memberships. (That last one almost swayed me until I realized I’d be more likely to use a membership to a pie-of-the-month club.)

But—and this is a big “but”—Medicare Advantage plans often come with networks. That means you might be limited to certain doctors or hospitals, depending on whether you pick an HMO or PPO plan. Since I split my time between two states, the idea of having a plan that only worked in one area didn’t sit right with me. I like my freedom too much, it just seems like too many caveats that might make Medicare Advantage plans more expensive and unnecessarily complicated.

The next thing I had to consider was prescriptions. If you go with Original Medicare, you’ll need a standalone Part D plan to cover your medications. These plans vary widely, so it’s worth checking which one covers your drugs at the best price. Medicare’s Drug Plan Finder tool online was a lifesaver here. I typed in my medications, and it showed me how each plan stacked up—cost, pharmacy options, and estimated annual out-of-pocket expenses. It felt like online shopping, only less fun.

With Medicare Advantage, most plans include drug coverage already, so it’s one less thing to add—but make sure your prescriptions are on their formulary (the fancy word for “approved drug list”) before you sign on the dotted line. Nothing’s worse than thinking you’ve got coverage, only to find out your medication isn’t part of the deal. Ask me how I know.

Another thing I had to think about was my overall health. If you have chronic conditions, need regular care, or anticipate a big procedure (like a joint replacement or cataract surgery), you’ll want a plan that doesn’t surprise you with big copays or restrictive networks. I looked at my past two years of medical use and asked myself, “If this pattern continues, which plan gives me peace of mind—and doesn’t eat into my travel budget?”

Total cost was the last big piece of the puzzle. Some Advantage plans have $0 premiums, which sounds amazing—until you realize they can still come with high out-of-pocket costs. On the flip side, a good Medigap plan may cost more each month, but it can virtually eliminate those surprise bills. It’s really about what kind of spender you are: the “low premium, high risk” type, or the “pay more up front, sleep better at night” type. I fall into the second category. I’d rather budget now than panic later. It just depends on your situation I guess.

One final piece of advice: don’t go it alone. I talked to a Medicare counselor from my state’s SHIP (State Health Insurance Assistance Program), and it was completely free. They helped me compare plans based on my actual needs—not what some slick ad said I should want. Also, I steered clear of plans that felt too salesy. If someone’s pushing a plan like a used car, I say “thank you, next.”

Choosing a Medicare plan takes some time and thought, but it’s time well spent. Don’t let the sea of options drown you, just take it step by step. Start with what you know (your doctors, your meds, your travel habits), and build up from there. And don’t be afraid to change your plan during Open Enrollment if your needs change. Medicare isn’t a life sentence—it’s more like a buffet where you get to go back for seconds once a year.

In the end, I chose a Medigap plan with Part D. It fits my lifestyle, lets me travel without stressing, and covers the care I need with very few surprises. It took a few evenings of comparison shopping, a lot of coffee, and a little swearing under my breath—but I got there. And you will too.