Interview with Jessalyn Pito, Licensed Insurance Agent on Medicare Annual Enrollment
Medicare annual enrollment begins October 15, and the best time to prepare is before the calendar fills up and deadlines create unnecessary pressure. Medicare can feel like a maze, but awareness, a careful review, and a conversation with a trusted professional can make the process far less stressful.
Key Takeaways
Schedule a Medicare plan review before October 15 rather than making last-minute decisions.
Review your Annual Notice of Change for premiums, copays, deductibles, and prescription coverage changes.
Consult a licensed agent before turning 65 if you have employer coverage or contribute to an HSA.
Do not rely on unsolicited calls or casual advice for important Medicare enrollment decisions.
Table of Contents
Why Medicare Guidance Matters
What motivated you to help people navigate Medicare?
I came into this industry because of my family. My mother was diagnosed with pancreatic cancer, and after she passed away, I knew I wanted to be a person who could help others find their way through the Medicare maze.
I treat my clients like family. Medicare is confusing and complicated, and that confusion can make people vulnerable to misleading information and scams. Many people receive a constant stream of phone calls, pitches, and promises that are not always clear or accurate.
You have paid into the Medicare system throughout your working life. This is not the time to put your health care needs into the hands of a stranger who calls out of the blue. Whenever possible, work with someone local and meet face to face. Find someone who can help you understand your choices and remain available after enrollment, not simply place you into a plan and disappear.
At JP Maven Insurance Benefits, we do not just put people in a plan. We become part of the plan, providing service throughout the year.
What to Do Before Medicare Annual Enrollment Begins
What is the first thing someone should do to prepare for annual enrollment?
Pick up the phone and get on your agent’s calendar now. Whether you work with my team, another licensed agent, or someone you have used in the past, do not wait until the last minute.
Think about holiday shopping. Decisions made in a frenzy are not always the best decisions. The same is true for Medicare coverage. October 15 arrives quickly, and a review takes time when you want to consider all your options carefully.
Even if you feel perfectly happy with your current plan, do not assume it will look the same next year. Coverage, premiums, copays, deductibles, and prescription benefits can change. A yearly review is about making sure the plan that worked this year still fits your health care needs next year.
Why should I review my plan if I am satisfied with it?
Because your plan may not stay the same. A plan can change in several meaningful ways, including:
Monthly premiums
Copays for medical services
Deductibles
Prescription drug coverage
Whether the plan remains available for the following year
The last thing anyone wants is to set it and forget it, then arrive at the pharmacy in January and discover a prescription is no longer covered or costs more than expected. Awareness is the key word. Know what your options are before a surprise becomes a problem.
How to Review Your Medicare Annual Notice of Change
What is the Medicare Annual Notice of Change, and why is it important?
The Medicare Annual Notice of Change explains how your current insurance plan is changing for the following year. It is an important document because it shows you exactly what may be different before you make your annual enrollment decisions.
Your insurance company is required to have it in your mailbox by September 30. First, make sure you actually received it. Mail can be misplaced or delivered to the wrong address, so do not assume it never came simply because you have not seen it.
What should I do if my Annual Notice of Change never arrives?
Call Member Services using the phone number on the back of your insurance card and request another copy. It is worth taking the extra step, because this document gives you a direct look at the coming year’s coverage changes.
What should I look for in the notice?
Pay particular attention to changes in premiums, copays, deductibles, and the status of the plan itself. Then look closely at how those changes could affect your own care and prescriptions.
There are significant changes ahead for 2027, which makes reviewing this information especially important. Do not wait until after coverage takes effect to learn that your plan has changed in a way that affects your budget or treatment.
For additional official Medicare resources, visit Medicare.gov.
Turning 65 While Still Working
Should someone speak with a licensed insurance agent before turning 65 if they still have employer coverage?
Absolutely. Reach out a few months before you turn 65. More people are working past 65 as they move toward their full retirement age, and that can make Medicare decisions more complicated.
Medicare and Social Security have completely different rules. Just because someone at the water cooler or a family gathering says you must enroll in Medicare at 65 does not mean that advice applies to your situation.
You may or may not need to enroll in Medicare while you have employer coverage. The right answer depends on your work situation and benefits, which is why a personal conversation matters.
What is the risk of relying on casual advice about Medicare enrollment?
It can lead to expensive mistakes. For example, someone may enroll in Medicare because they were told they had to, while also contributing to a health savings account, or HSA. That can create a penalty situation.
There are also important timing rules when employment ends. Someone who receives a retirement package or a golden handshake with a year of employer benefits should not assume those benefits eliminate every Medicare enrollment consideration.
I have seen people miss their eight-month enrollment window and then find they cannot enroll in Medicare until January. That is precisely why it helps to have a conversation early. It costs nothing to check your situation, even if the answer is simply that you are fine where you are.
Getting Help Without Added Cost
Does it cost money to work with a Medicare advisor?
My services are complimentary. The only thing you have to pay is attention.
I serve clients in Connecticut and beyond, including people who have moved away but wanted ongoing help with their insurance needs. The goal is not to make Medicare more complicated. The goal is to make sure you understand your options and can make decisions with confidence.
What is your final advice for anyone approaching Medicare enrollment?
Do not wait. Get on the calendar, review your Annual Notice of Change, and talk through your individual work, retirement, prescription, and coverage situation.
Medicare is not something to handle on autopilot. A little preparation now can protect you from unpleasant surprises later. When clients work with Jess, they do not stress.
Medicare Annual Enrollment FAQ
When does Medicare annual enrollment begin?
Medicare annual enrollment begins October 15.
When should I receive my Annual Notice of Change?
Your insurance company is required to have the notice in your mailbox by September 30. If it does not arrive, call the Member Services number on the back of your insurance card to request a copy.
Should I review Medicare coverage every year?
Yes. Even if you are happy with your current coverage, premiums, copays, deductibles, prescription coverage, and plan availability can change for the following year.
Do I have to enroll in Medicare at 65 if I am still working?
Not necessarily. Medicare and Social Security follow different rules, and the right choice depends on your employer coverage, retirement situation, and other factors. A licensed agent can help you review your specific circumstances.
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