One Medicare Decision Can Affect You For Years.

Making Medicare decisions shouldn’t be confusing. My job is to help you understand every option before you decide.

The good news? Most costly Medicare mistakes are completely avoidable—if you understand your options before you enroll. Whether you’re turning 65, still working, retiring, losing employer coverage, or choosing between Medicare Advantage and a Medicare Supplement, I’ll walk you through it.

Choose Your Situation Schedule My Free Medicare Consultation

Independent Medicare Advisor • Education First • No Cost to You

Cindy Kowalski, independent Medicare advisor and founder of Eligry
Cindy Kowalski Founder & Licensed Medicare Advisor

Start Here

Which Situation Best Describes You?

Pick the path that fits where you are today. Each one leads to plain-English guidance built around your decision—not a sales pitch.

Turning 65

I’m new to Medicare. Help me understand where to start.

Where to Start

Working Past 65

Should I keep my employer insurance, or enroll now?

Compare Employer vs. Medicare

Retiring or Losing Coverage

My coverage is ending. What should I do first?

Plan My Transition

Advantage vs. Supplement

Help me compare my two main Medicare paths.

Compare My Options

Why It Matters

The Medicare decision you make today may determine the options you have years from now.

Some Medicare decisions are easy to make. Others are difficult—or even impossible—to undo later. That’s why understanding every option available to you before you enroll matters so much.

The Big Picture

There Are Three Medicare Decisions That Matter Most.

I help people make Medicare’s biggest decisions before they become Medicare’s biggest mistakes. Get these three right, and you avoid the ones that are hardest to undo.

01

Should I enroll now?

Working Past 65

See how to decide
02

When should my Medicare begin?

Leaving Employer Coverage

Plan the timing
03

Which type of Medicare should I choose?

Advantage vs. Supplement

Compare the two paths
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If the best Medicare option for you is one I can’t enroll you in, I’ll tell you anyway.”

Why Eligry Is Different

I don’t start by recommending a plan.
I start by understanding your situation.

Independent Advice

Carrier-agnostic guidance, not one company’s script.

Education First

You’ll understand the “why” before any decision is made.

No Sales Pressure

Take the time you need. Enroll only when you’re ready.

Personal Guidance

You work directly with me—from first question to enrollment.

No Email Wall to Start

Free Medicare Resources

Use these on your own time. They’re built to help you think clearly—whether or not we ever talk.

2-Minute Quiz

Employer vs. Medicare Quiz

Still working at 65? See whether to enroll now or keep your employer plan.

Take the Quiz
2-Minute Quiz

Advantage vs. Supplement Quiz

The first Medicare decision is Supplement vs. Advantage. See which fits you.

Take the Quiz
Free Checklist

Retirement Checklist

A step-by-step list of what to handle—and when—as you approach retirement.

Get the Checklist
Free Download

The A-to-Z Guide to Medicare

My plain-English 2026 guide walks you through every part of Medicare.

Download the Guide

In Their Words

What People Say After We Talk

★★★★★

Cindy explained the difference between Advantage and a Supplement in a way that finally made sense. I never felt rushed, and I understood exactly what I was choosing.

BM
Barbara M. Florida
★★★★★

I was still working at 65 and had no idea what to do about Part B. She walked me through my employer plan and saved me from a penalty I didn’t know existed.

RK
Raymond K. Indiana
★★★★★

What stood out was that she told me about options she couldn’t even sell me. That’s when I knew I was getting honest advice.

DP
Denise P. Florida
Cindy Kowalski, founder of Eligry

Meet Cindy

I started Eligry because I almost got it wrong myself.

I nearly enrolled in a Medicare Advantage plan without knowing Supplements even existed—until my sister stopped me and asked if I’d compared them. That one question changed everything.

So I became an independent advisor, licensed in 22 states, to do the opposite of what almost happened to me: show people every option available to them—not just the plans that are easiest to sell.

Making Medicare decisions shouldn’t be confusing. My job is to help you understand every option before you decide.

— Cindy Kowalski, Founder of Eligry

Read My Story

Learn Before You Decide

Short Videos on the Big Decisions

A few minutes each, in plain English. No jargon, no pressure.

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Working Past 65
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Retiring Soon
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Advantage vs. Supplement

Common Questions

Medicare Questions I Hear Most

I’m turning 65. Should I enroll in Medicare now?
It depends on whether you have other qualifying coverage. If you’re not covered by active employer insurance, you’ll usually want to enroll during your Initial Enrollment Period to avoid lifelong late penalties. If you’re still working, you may be able to delay. I’ll help you confirm which applies to you.
Should I delay Part B if I’m still working?
Sometimes. If you have active coverage through a large employer, you may be able to delay Part B without penalty and enroll later through a Special Enrollment Period. But the rules depend on your employer’s size and plan type, so it’s worth confirming before you decide—an incorrect assumption here can be costly.
What’s the difference between Medicare Advantage and a Medicare Supplement?
They’re two different ways to receive your Medicare coverage, and choosing between them is the first real decision. A Supplement pairs with Original Medicare and works with almost any doctor who accepts Medicare; an Advantage plan bundles your coverage through one insurer, usually with a network and extra benefits. I’ll explain the trade-offs for your situation.
Can I keep my employer insurance and Medicare together?
Often, yes. Many people keep employer coverage and add Medicare Part A, or coordinate both together. Which one pays first depends on your employer’s size. The first thing to check is whether delaying or enrolling makes more sense for your specific plan, and I can walk you through that comparison.
Does Medicare cover prescription drugs?
Not automatically. Prescription coverage comes through Part D—either a standalone plan alongside Original Medicare and a Supplement, or built into most Medicare Advantage plans. Skipping Part D when you’re first eligible can trigger a lifelong late penalty, so it’s worth setting up even if you take few medications today.
Can I switch from Medicare Advantage to a Supplement later?
You can request to switch, but it isn’t guaranteed. Outside of specific windows, moving from Advantage to a Supplement can require medical underwriting, which means you could be denied or charged more based on your health. That’s why the first decision—Supplement versus Advantage—deserves careful thought up front.
Do I need Medicare if I’m still working at 65?
Not always. If you have qualifying coverage through a current employer, you may be able to delay parts of Medicare without penalty. Some people benefit from enrolling in Part A right away, while others shouldn’t if they contribute to an HSA. I’ll help you sort out which situation is yours.
How much does it cost to work with you?
Nothing. My services are free to you. Like most independent advisors, I’m compensated by the insurance carriers when you enroll, and that compensation is the same whether you enroll on your own or with my help. You get guidance now—and someone to call later—at no added cost.
When can I enroll in or change my Medicare plan?
It depends on the change. Your first window is the seven-month period around your 65th birthday. After that, the Annual Enrollment Period runs October 15 to December 7 for coverage starting January 1. Certain life events, like losing employer coverage, open a Special Enrollment Period. I’ll help you find yours.
I already have a plan but I’m not sure it’s right. Can you review it?
Yes, and it’s worth doing. Plans change every year, and so do your needs. I can review what you have, explain how it compares to your other options, and tell you honestly whether it still fits or whether it’s worth adjusting at your next enrollment window. There’s no pressure to switch.
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Making Medicare decisions shouldn’t be confusing. My job is to help you understand every option before you decide.

Whatever Medicare decision you’re facing…

Let’s make sure you understand every option available to you before you decide.

Schedule My Free Medicare Consultation

A note on how I work: I’m appointed with most major Medicare carriers, but my priority is helping you make the right decision. I’ll explain every Medicare option available to you—even those I can’t enroll you in—so you understand the complete picture before choosing a plan. My role is education first, sales second.

Not affiliated with or endorsed by the government or federal Medicare program.