Lisa Schaad, Medicare Insurance Agent

Answer: When someone is brand-new to Medicare, I start by keeping it simple. There’s so much information out there that it can feel overwhelming, so I focus first on the basics—what Parts A, B, C, and D are, and how they work together. From there, we walk through their personal situation—do they take medications, do they have doctors they want to keep, what’s most important to them in coverage.

I use plain language, no jargon, and I pause often to check if it’s making sense. I always tell people: “There are no silly questions—if you’re wondering about it, it matters.” My goal is that by the end of the conversation, they not only have the right plan but also feel confident they understand why it’s the right plan.

Answer: Your first chance to enroll is your Initial Enrollment Period—that’s 3 months before, the month of, and 3 months after your 65th birthday. If you’re already on Social Security, you’ll be enrolled automatically; if not, you’ll apply through Social Security.

Answer: What I enjoy most is the conversations. Medicare can feel so overwhelming, and I love being able to slow it down, explain things in plain language, and watch that look of relief when someone realizes, “Okay, I get this now.”

For me, it’s not just about the plans—it’s about the people. Every client has a story, a family, and real concerns, and being able to guide them to something that gives both protection and peace of mind is truly rewarding.

Answer: Since Medicare Supplement benefits are standardized, the main way to save money is by comparing prices between companies. Just keep in mind—if you’re outside your open enrollment window, switching may involve health questions, so it’s smart to check first.

Answer: Life insurance is really about protecting the people you love and making sure money is there when it’s needed most. In financial planning, it can cover final expenses so your family isn’t left scrambling to come up with money for a funeral, replace lost income if someone passes away, or even help leave a legacy for children and grandchildren.

For some people, certain policies can also build cash value over time that can be used while you’re still living. But at its core, life insurance gives peace of mind—it’s a safety net in your plan so that no matter what happens, your family is financially supported.

Answer: Medicare Advantage plans can have some really nice extras, but sometimes the way they’re advertised makes them sound bigger than they really are. For example, the “$0 premium” plans can still come with copays, deductibles, and a maximum out-of-pocket cost that you’ll want to pay attention to.

Another one is the extra perks like gym memberships, dental, or vision. They can be helpful, but they’re usually limited—like only covering cleanings, a set dollar amount for glasses, or a network of dentists that may not include the one you like.

The real value of a plan is in how it covers your doctors, hospitals, and prescriptions—not the freebies. I always tell people: enjoy the extras if they fit your needs, but don’t pick a plan based on those alone.

Answer: It can definitely feel random when you compare what you’re paying to a friend’s plan, but there’s a reason for it. Medicare Advantage and Part D drug plans are approved by Medicare but run by private companies, and each company sets their premiums, copays, and extras based on your ZIP code and county. That’s why your friend in one area might pay $0 while in your area the same type of plan costs more.

On top of that, your income can affect what you pay for Part B and Part D through something called IRMAA (Income-Related Monthly Adjustment Amount). It’s basically an extra charge added by Medicare if your income is above certain levels, and it makes your monthly cost higher than someone else’s.

So, it’s not random—but it does depend a lot on where you live and your income situation.

Answer: If you’re already retired and collecting Social Security when you turn 65, you don’t have to do much—Medicare usually signs you up automatically. Your Part A (hospital coverage) and Part B (medical coverage) will start the month you turn 65, and you’ll get your red, white, and blue Medicare card in the mail a few months before.

The part you still need to decide is whether you want to add a Medicare Advantage plan, a Part D drug plan, or a Medicare Supplement. Social Security gets you into Original Medicare, but you still have choices on how to set up the rest of your coverage.

Answer: When you’re first getting on Medicare, you have your Initial Enrollment Period—that’s your 7-month window around turning 65 to choose your coverage. After that, the times you can make changes are:

Annual Enrollment (Oct 15–Dec 7): This is when anyone on Medicare can join, drop, or switch plans for the next year.

Open Enrollment (Jan 1–Mar 31): This one’s only for people already in a Medicare Advantage plan, and it gives you one chance to switch to another Advantage plan or back to Original Medicare.

Special Enrollment Periods: These pop up if your life changes—like you move, lose coverage, or qualify for Extra Help.

So if you’re new, you’ll use your Initial Enrollment first—but once you’re settled in, these other windows are the ones to remember going forward.

Answer: One of the most important questions people don’t think to ask is, “How will this plan work for me if my health changes down the road?” It’s easy to focus on what you need right now, but the real value of a plan shows up when life takes a turn. Asking that helps you see past just today’s costs and think about how well the plan will protect you in the future.

Answer: A good Medicare agent makes the whole process less overwhelming. Instead of you trying to sort through dozens of plans and rules on your own, an agent can explain your options in plain language, compare plans side by side, and point out things you might not know to look for.

The biggest reason, though, is support. Life changes, health needs change, and plans change every year—having an agent means you have someone in your corner who can review things with you and make sure you’re still in the right spot.

Answer: This comes up a lot, and I know it can feel overwhelming when even Part D doesn’t make the meds affordable. The main programs I’d look at are Extra Help through Social Security, your state’s Medicare Savings Programs, and sometimes State Prescription Assistance if your state offers it. Many drug companies also have Patient Assistance Programs for folks who qualify.

If it were me, I’d start with Extra Help because it’s usually the quickest relief. Then check with your state Medicaid office about the Medicare Savings Programs. And don’t forget—your agent can walk you through applying so you don’t feel like you have to figure it all out on your own.