Medicare Advice: Mistakes to Avoid When Enrolling in Medicare

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Medicare is the federal health insurance for people 65 and older and younger people who meet certain criteria. It can help enrollees pay for essential health care and major medical expenses. However, choosing a Medicare plan that best meets your needs can often be confusing. You must navigate multiple plan options and enrollment periods and understand Medicare’s various parts. Further, mistakes made during Medicare enrollment can significantly impact your finances and health care coverage. This blog is intended to provide an overview of common Medicare enrollment mistakes and advice on how to avoid them.

Our Medicare Enrollment Advice: Avoid These Common Blunders

Missing Enrollment Periods

You can only join, switch, or drop a plan during certain times. Failing to enroll, adjust, or add health insurance during the correct enrollment period could be a costly mistake. There are multiple enrollment windows you should be aware of, including the following:

  • Initial enrollment period—If you’re new to Medicare, you can enroll in a health care plan when you turn 65. Generally, this seven-month period begins three months before your 65th birthday and ends three months after the month you turn 65.
  • General enrollment period—The annual Medicare open enrollment period runs from Oct. 15 to Dec. 7 every year. During this time, individuals with Medicare can make coverage changes that will go into effect on Jan. 1 the following year.
  • Medicare Advantage enrollment period—If you’re already enrolled in a Medicare Advantage plan, you can switch or drop your plan in the first three months after you get Medicare or during the enrollment period, which runs from Jan. 1 to March 31 each year.
  • Special enrollment period—You may be able to adjust your health care plan outside of the initial and general enrollment periods without incurring a penalty if you experience certain life changes during the year. You may be eligible for this enrollment period if you lose your other health care or move to a new address.

Failing to Review Your Plan Options

Medicare offers various coverage options, including Original Medicare (Part A and Part B), Medicare Advantage (Part C), and Medicare prescription drug plans (Part D). The type of coverage you need will vary depending on your health care needs, location, the insurance your doctors accept, and your financial situation, among other factors. Not taking the time to understand which health care plan best suits your needs can result in inadequate coverage or unexpected expenses. For example, signing up for a health care plan that works for your spouse, neighbor, or friend without evaluating your unique situation and health care needs can have costly ramifications.

Not Understanding the Differences Between Medicare and Medicare Advantage

If you’re eligible for Medicare, you can choose between original Medicare and Medicare Advantage. Original Medicare offers comprehensive coverage for most medically necessary services and supplies. Medicare Advantage plans provide coverage for all the same services and supplies with extra benefits, such as vision, hearing, and dental services. Your choice of plan will also impact the cost of your health care and your doctor and hospital choice.

Not Understanding Medicare Penalties

If you don’t enroll in Medicare Part A and Part B during your initial enrollment period, you may have to wait to sign up. This could result in a gap in your coverage, leading to costly out-of-pocket medical expenses if you require health care during this period. Furthermore, you may have to pay a lifetime late enrollment penalty that increases the longer you wait to sign up. In some instances, your Medicare Part B premium may increase by 10% for every 12 months you were eligible for Medicare Part B but did not have Medicare Part B. Additionally, for every 12 months you delay signing up for a Medicare Part D plan, your monthly premium may increase by 1%. These penalties typically last for as long as you have Medicare. Therefore, it’s crucial that you understand these penalties when deciding to enroll in a health care plan.

Choosing the Wrong Coverage

Not understanding your coverage needs can result in costly and unexpected out-of-pocket expenses. Medicare Part A is usually free, but Medicare Parts B, C, and D all require a monthly premium. Although it may be tempting to select the cheapest health care option, inadequate coverage could cost you more in the long run. When selecting your health care plan, it’s also important to consider your future needs, such as potential surgeries and chronic conditions that could require more coverage than you currently require.

Overlooking Prescription Drug Coverage

Medicare prescription drug plans (Part D) help pay for prescription drugs you need. These plans are optional and are provided through private insurers approved by the federal government. If you don’t have other creditable prescription coverage and you don’t sign up for Medicare prescription drug coverage when you first enroll, you may have to pay a late penalty if you enroll in Medicare Part D coverage later. As such, you may want to consider getting prescription drug coverage even if you aren’t on any prescription drugs at the time of your Medicare enrollment.

Prescription drug coverage and costs may vary every year. Therefore, it’s crucial that you review and compare plans annually so that you can make the best decision for yourself during open enrollment. If you’re not sure where to begin, you can enter your prescription drugs into and see what plans it suggests.

Ignoring Medigap Policy Options

Medigaps—also known as Medicare Supplement Insurance—are supplemental health insurance policies that can help pay some of the out-of-pocket medical expenses that Medicare doesn’t cover. For example, it may help pay for your Medicare Part A hospital deductible or your Medicare Part B coinsurance. You may be able to choose from as many as 10 different Medigap policies, depending on your location. The best time to buy a Medigap policy is during your Medigap open enrollment period, which is a six-month window that begins when you turn 65 years old and have enrolled in Medicare Part B. During this period, you cannot be denied coverage if you have an existing health condition, and Medigap insurers are required to sell you a plan at the best available rate. If you try to buy Medigap outside of this window, insurance companies may deny you coverage for existing health problems.

Assuming You Can’t Afford Medicare

If you have a limited budget, you may believe you can’t afford Medicare. Fortunately, there are several programs that may be able to assist you with your health care costs. Before open enrollment passes, you should review your financial assistance options, including the following:

  • Medicare Savings Programs (MSPs) help pay your monthly Part B premium. They may also help with Medicare cost sharing. Contact your state health insurance program (SHIP) at to learn if you’re eligible for an MSP.
  • Extra Help can help pay for the costs of Medicare Part D prescription drug coverage. Contact the Social Security Administration (SSA) at 800-772-1213 or visit the SSA website to learn if you are eligible for Extra Help.
  • State Pharmaceutical Assistance Programs (SPAPs) exist in some states to help eligible individuals pay for prescriptions. Contact your SHIP at to learn if there is an SPAP in your state.

Interested in More Medicare Advice?

Choosing your health care plan is one of the most important decisions you’ll make all year. Making mistakes when enrolling in Medicare can result in costly and avoidable health care expenses, potentially leading to significant financial hardship.

For more Medicare enrollment advice, visit the Medicare website or contact our dedicated Acentria Team today.


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Rob Wagner

Executive Vice President | Director of Sales, Southeast Region

With over 15 years of insurance industry experience, Rob focuses on growing organic growth throughout the entire Southeast region for both Acentria Insurance and Foundation Risk Partners. Working alongside both executive leadership and territory sales leaders, Rob is instrumental in producer training, increasing retention and expanding our organizational footprint.

As a self-proclaimed Army Brat, he was born in Fort Benning, GA, but has moved 27 times and resided in 40 different houses… all before college! His father proudly served our country for 28 years! As a graduate of Florida State University with a degree in Business Management, Rob also holds an MBA from Stetson University. A producer at heart, he specializes in large property, senior living, management liability and workers’ compensation. He enjoys meeting new team members and finds his personal success in seeing producers succeed.

In his free time, he enjoys spending time with his wife of 22 years and their two daughters. Together they enjoy boating, offshore fishing and exercising.

Mike Freeman

Mergers & Acquisitions

Leading the Acentria Mergers & Acquisitions team, Mike works with those agency principals and leaders who are interested in furthering a potential partnership with Acentria Insurance.  With over 35 years of finance and insurance experience, Mike and his team showcase the various benefits of partnering with Acentria. He works with principals through the initial phases to evaluate agency operations, books of business as well as planning and implementing fully comprehensive migration and implementation plans. He served 25 years in the banking industry in various executive-level positions transitioning to insurance in 2011 as Chief Financial Officer for Acentria Insurance. In 2017, Acentria Insurance partnered with Foundation Risk Partners where his major focus became leading Acentria Insurance’s mergers and acquisitions team.  

Mike is a graduate of Auburn University. He is dedicated to serving his community having held numerous leadership positions including Chairman for the American Heart Association; Chairman Mental Health Association; Chairman Destin Chamber of Commerce and Board Member for United Way Okaloosa-Walton Counties. Mike is a 27-year resident of Destin, FL and enjoys spending time with his wife of 35 years, Yvonne and their two adult children and their families.

Jenny Cirioni

Vice President, Operations
Northeast, Florida

Todd Lawrence

Executive Vice President
Southeast Florida

Rob Wagner

Executive Vice President
Southwest Florida Region

Alan Florez

Executive Vice President, National Sales

Alan leads new business growth strategies and expansion, guides the development of resources and training for Sales Producers and their partnerships with Carriers. With over 15 years of industry experience, Alan also leads the Acentria Public Risk divisions working with municipalities and government entities for their coverage needs. He was appointed to the Halifax Health Board of Commissioners December 2020 and also serves as an Executive Committee member for our parent company, Foundation Risk Partners.

Previously, Alan served as Governor Jeb Bush’s Deputy Director of Legislative Affairs and Special Assistant. He is a former member of the University of Central Florida Board of Trustees and currently volunteers his time with the Florida Council of 100, Futures Foundation of Volusia County Schools and the Community Foundation of Flagler and Volusia. Alan holds a bachelor’s degree in Political Science from the University of Central Florida.

Anne Kraus

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Commercial Lines Operations

Teresa Fillmon

Vice President
Small Business Unit

Alex Doberstein

Vice President
Benefits Resource Leader

Eric Austin

Operations Lead
Port St. Lucie & West Palm Beach

Luke Wolkers

Executive Vice President
Employee Benefits

Chris Tolland

Executive Vice President
Northeast Florida Sales

Brian Stanton

Executive Vice President
Southeast Florida

Nathan Marks

Executive Vice President
Northwest Florida

Jason Cruse

Executive Vice President
Central Florida Sales

Jackie Shaw

Senior Vice President
Agency Operations

Jessica Parkhurst

Senior Vice President
Marketing & Branding

Doreen Castro

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Kendall McEachern


Kendall was a fundamental part of Acentria Insurance. As a co-founder, he brought more than 30 years of industry expertise to Acentria, helping transform the organization into a leading insurance provider. Beloved by team members, carrier partners and clients, he oversaw more than 400,000 insured multi-family units with property values greater than $22 billion, and over four million square feet of commercial office space and real estate buildings. Kendall has received numerous industry awards to include being recognized as a National Top Producer and Agent of the Year by both Insurance Business America and Insurance Journal. Away from the office, he served as chairman for the American Heart Association, actively participated in his church and golfing, watching sports and spending time with his family. Kendall passed away in January of 2021, leaving a lasting legacy on Acentria’s culture, success, industry-wide reputation – and on all of us fortunate to have worked alongside him.

Mary Lawless

President & Chief Operating Officer

As President and Chief Operating Officer, Mary brings over three decades of industry expertise to Acentria Insurance. With a strong focus on Mergers & Acquisitions, Mary is passionate about partnering with new agencies and leaders to continue the overall upward growth of Acentria. She works in conjunction with the CEO to lead and deliver specialized sales products, services and industry leading capabilities while implementing business and sales strategies to the Acentria sales team and carrier partners. Mary has direct oversight of all operational leaders throughout the entire organizational footprint and is responsible for operational financials and budgets.

She empowers her team members and because of it, is well respected by her peers and those she leads. Since her time with Acentria, Mary’s leadership has contributed to the agency’s exponential growth from 15 to well over 50 locations, increasing employment to over 700 team members, across the southeastern United States. Due to her leadership and contributions to the insurance industry, she has been nationally recognized as one of Insurance Business America magazine’s Elite Women and serves as a valuable member on the Executive Committee for Foundation Risk Partners, Acentria’s parent company. Prior to joining Acentria Insurance, Mary led operations for another national broker. Throughout her tenure, she has held a variety of management positions in Personal Lines, Select Business and Employee Benefits. Mary specializes in agency operations, partnerships and acquisitions and is truly passionate about developing team members to become great leaders.

When not shaping the future industry leaders at Acentria Insurance, Mary enjoys traveling and spending time with her husband, Pat and their family and friends.

Mitch Weinstein

Partner & Co-Founder

As partner of Acentria Insurance, Mitch plays an integral role in mergers & acquisitions. He focuses on seeking out strategic like-minded partners and agencies, across the southeastern United States, to partner and join the Acentria family.

Mitch has over 42 years of business leadership experience that ranges from law enforcement to the finance, healthcare and insurance industries. He was instrumental in developing the nation’s first “at-risk” managed care network for physical and occupational therapy serving the worker’s compensation industry. This network paved the way for a new managed care system, based on incentives.

Mitch is passionate about giving back to the youth of his community. He is an active supporter of the Boys & Girls Clubs of Polk County and believes in helping all young people reach their full potential. He is also the founder of Fallen First Reserve which is a non-profit organization dedicated to financially assisting those family members of First Responders killed in the line of duty and military members killed in action. Mitch also serves on the board for Fund the First.

Kevin Mason

Chief Executive Officer & Co-Founder

As Chief Executive Office of Acentria Insurance, Kevin focuses on developing insurance solutions that strengthen Acentria’s presence in the market and its commitment to client-relationships and exceptional service. With over 35 years of industry experience, he specializes in the overall growth of Acentria is passionate about bringing new talent to the organization both organically and through mergers and acquisitions. Through his leadership and the support of the Executive Leadership team, Acentria Insurance instills a positive corporate culture which has led the agency in being recognized as a leader within our industry as a Top 100 Workplace, Employer of Choice, Best Agency to Work For and several other national and regional accolades.

Before co-founding Acentria Insurance, Kevin served as Branch Manager for another national broker. Kevin holds the prestigious title as an Agent of the Year and five-time National Top Producer. He is also a key member of the Foundation Risk Partners Executive Committee, which is the parent company of Acentria Insurance, while also serving as the National Director for Carrier Relations. In addition, Kevin oversees the Sales Leadership Council, which encompasses sales leaders across the entire FRP footprint in an effort to develop and refine shared resources while offering producer training and development programs.

Kevin received a Bachelor’s Degree in Management from the University of West Florida. He is very active in his community and served over a decade on the Board of Directors of Destin Charity Wine Auction Foundation and remains as a trustee, which funds over 14 children’s charities along the Florida Panhandle. He is also a member of the Destin Chamber of Commerce, Community Association Institute and Florida Association of Insurance Agents. In his spare time, Kevin enjoys golfing, tennis, boating and spending time with his wife Laura, and their children.