Ask Yourself These 6 Questions Before You Get Medicare
Written by
Kerra Bolton
Edited by
Rebekah Evans
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Medicare comes with deadlines, options and fine print that can confuse even the most organized retiree.
One wrong assumption about timing, coverage or cost can leave retirees paying more than expected. Before signing up, it’s worth taking a moment to understand how the pieces fit together and what decisions can’t be undone. Ask yourself the six questions below before you get Medicare.
Also here’s how to plan for Medicare in 2026.
Am I Enrolling On Time?
Timing matters more than most people realize. Missing your initial enrollment window can mean higher premiums that last for life and coverage gaps that are difficult to fix later.
“You will be penalized and locked out permanently if you miss your Initial Enrollment Period (IEP) and are ineligible for a Special Enrollment Period (SEP),” said Kiara DeWitt, head of clinical operations at Medical Director Co, a medical staffing platform.
DeWitt said premiums increase 10% for every 12-month period a person delays enrollment, even if the delay is only a month. Over time, that can add up to thousands of dollars and leave beneficiaries without access to care or prescriptions for weeks or months.
Do I Understand What Medicare Covers — and What It Doesn’t?
Stephanie Jones, founder and CEO of iTAV, a software platform that helps simplify Medicare, said consumers should start by learning what each part of Medicare covers and what it leaves out.
“What are the different parts of Medicare (Parts A, B, C and D) and what do they cover?” Jones said. “Have I budgeted for premiums, deductibles and copayments over the next 30 years?”
After assessing their budget, Jones said consumers should ask whether they need additional coverage and whether they can afford to cover what Medicare doesn’t.
What Were My Medical Expenses in 2025?
Before reviewing Medicare options, consumers should look back at their recent healthcare spending to see where their money actually went.
Whitney Stidom, vice president of consumer enablement at eHealth, said consumers can prepare for the Medicare Annual Enrollment Period by reviewing what they spent on monthly premiums and out-of-pocket costs over the past year.
They should decide whether those monthly payments are still affordable and how an increase might affect their budget.
“Understanding expenses like these is an important step when reviewing your coverage options for 2026,” Stidom said.
Have I Compared My Medicare Options?
Choosing between Original Medicare, Medicare Advantage (MAPD) and Medigap coverage starts with understanding costs and fit.
Jack Glasker, health insurance broker and advisor at Affordable Healthcare Solutions, said consumers should calculate the cost of Part A and B and whether income-related surcharges (IRMAA) apply.
They should also evaluate whether to combine Original Medicare with a Medigap policy or switch to an Advantage plan, depending on current coverage and employment status.
Glasker said retirees should ask practical questions, such as: “What providers do I see, how often and what prescriptions do I take?”
Comparing premiums, cost-sharing and prescription expenses across plans can reveal which option truly meets long-term needs.
Do I Need Supplemental Coverage?
Even with Medicare, consumers are responsible for costs like coinsurance, deductibles and services such as dental, vision and hearing care.
Jeff Ganow, senior vice president of Medicare Supplemental Solutions at Mutual of Omaha said many people focus on premiums but overlook these expenses.
“Thinking about whether you prefer predictable costs and nationwide provider access or lower premiums with network restrictions, can help you choose between Medigap and Medicare Advantage,” he added.
Timing also matters. Ganow said most states offer only one guaranteed chance to enroll in a Medigap plan without medical underwriting. Waiting could mean higher premiums or denial later.
Am I Thinking Long-Term?
DeWitt said that too many people rush through Medicare enrollment as if it were just paperwork.
“They treat it more like a sign-up form than a plan,” she said. “‘What plan looks good?’ is not the right question. But ‘What will my total healthcare spending be if I stay on this for 25 years?’ That’s a $200,000 decision. It also deserves more homework than a ten-minute phone call with a stranger broker.”
Taking time to research options, compare long-term costs and seek reliable guidance can turn a quick decision into a sustainable plan for the future.
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