One Medicare Decision Can Affect You For Years.

Making Medicare decisions shouldn’t be confusing. My job is to help you understand your options 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 Consultation Call 352-464-4400

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 can become much more difficult to change later. That’s why understanding your Medicare options before you enroll matters so much.

Working Past 65, Retiring, or Choosing Medicare?

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?

Supplement vs. Advantage

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

On Your Side

Why Choose an Independent Medicare Advisor?

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 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 Kowalski was extremely helpful in helping me decider the confusing business of Medicare and all the choices. She spent an enormous amount of time educating me on the different choices that fit my particular needs. I would recommend her highly.

RG
Robbie G. St. Petersburg, FL
Cindy Kowalski, founder of Eligry
  • Independent Medicare Advisor
  • Licensed in 22 States
  • AHIP Certified
  • No-Cost Medicare Reviews

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 their Medicare choices—not just the plans that are easiest to sell.

I spent decades helping people make complex business decisions before becoming a Medicare advisor. I bring that same clarity to what may be the most important decision of your retirement.

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

— Cindy Kowalski, Founder of Eligry

Read My Story

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 late enrollment 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—generally one with 20 or more employees—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. One key difference: Medicare Supplements generally don’t include prescription drug coverage, while most Medicare Advantage plans do. I’ll explain the trade-offs for your situation.
Can I keep my employer insurance and Medicare together?
Often, yes—while you’re in active employment. Many people keep active employer coverage and add Medicare Part A, or coordinate both together. Which one pays first depends on your employer’s size. (This changes once employment ends, which is where people often get tripped up.) 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 late enrollment penalty that may continue for as long as you have Part D coverage, 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. Some states also provide additional consumer protections, so it’s worth checking the rules where you live.
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—and people often confuse two windows. Your Medigap Open Enrollment is a one-time six-month window tied to your 65th birthday and Part B start. The Annual Enrollment Period is the yearly October 15–December 7 window, for changes effective January 1. Life events like losing employer coverage can also open a Special Enrollment Period. I’ll help you find the one that applies to you.
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 your options before you decide.

Whatever Medicare decision you’re facing…

Let’s make sure you understand your Medicare choices before you decide.

Schedule My Medicare Review Call 352-464-4400

We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.

How I work: I’m appointed with a limited number of carriers, so there are plans I can’t enroll you in. That doesn’t mean I won’t talk about them. When I review your situation, I look at the options that actually fit you—including the ones I can’t sell—and I’ll tell you what I find either way. If the better fit is somewhere I can’t take you, I’ll say so and point you to Medicare.gov or 1-800-MEDICARE.

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