The Medicare Decisions You Only Make Once: A Plain-Language Guide for People Approaching 65

About This Blog

Danielle has spent nearly two decades guiding people through the Medicare transition, and she has seen the same avoidable mistakes cost people thousands of dollars in penalties or lock them out of the coverage they actually need.

On this week's episode of Safe Money Radio, host Brett A. Blake sits down with Danielle Roberts, co-founder of Boomer Benefits, to talk about Medicare. Brett went into the conversation assuming Medicare was something a reasonable person could figure out on their own. He came out of it saying, out loud, that he would have gotten it wrong.

If the host of a retirement income show was ready to delay Medicare and save the government some money, the rest of us should probably stop assuming we're going to intuit our way through this.

The Assumption That Costs You  

The story most people carry into their 60s is that Medicare is like every other insurance decision they've ever made. Read the packet, pick the plan with the lowest premium, and if it doesn't work out, fix it during open enrollment. That story is wrong in a few important ways, and the ways it's wrong are the ones that stack up over the next twenty years.

Medicare has premiums, deductibles, and cost sharing, just like every other kind of health insurance. Even during working years when an employer paid the bill, someone was paying a premium. Assuming Medicare is free is the first mistake in Danielle's book. She has had people call her office on their 65th birthday genuinely surprised to learn there's a monthly premium at all.

The Windows That Don't Reopen  

Your initial enrollment period is a seven-month window: the three months before you turn 65, your birthday month, and the three months after. Miss it and the Part B late-enrollment penalty adds 10% to your premium for every 12 months you delayed. Danielle told the story of a man who called her office with a 70% Part B penalty because he'd been in good health his whole life and kept putting it off. The Part D penalty accrues similarly and lasts for as long as you have Part D. Delay five years and you might pay a 60% penalty on top of your Part D premium every month, forever.

Those are the penalty windows. The bigger one is the coverage window.

When you first enroll in Part B, you have a one-time six-month window to buy a Medicare supplement, also called a Medigap plan, with no health questions asked. In most states, once that window closes, insurers can underwrite you. If you have an ongoing cancer diagnosis or another serious condition at that point, they can decline you. Danielle calls this the big mistake in her book for a reason. The annual fall election period does not reopen it. Every October, people call Boomer Benefits asking to get a Medigap plan because they got sick during the year, and Danielle's team has to tell them the fall window is not for that.

Coverage Bought for the Wrong Reason  

Medigap plans supplement Original Medicare. They cost more up front and cover more on the back end, and you can see any provider in the country that accepts Medicare.

Medicare Advantage plans cost much less up front. Many carry a zero-dollar premium and some throw in perks like a gym membership. In exchange you agree to play by the plan's network rules. Your doctor might not be in the network. Your prescription might not be covered. In an urban area, zero-premium plans are common and attractive, but the question is whether the plan covers the specialist you actually need and whether your maximum out-of-pocket makes sense if something serious happens.

Danielle's caution is direct. Do not buy for the perks. Do not buy for the cheapest premium. You are buying coverage for when your kidneys fail, when you get diabetes, when you get cancer. That is what the coverage is for.

What Medicare Doesn't Cover  

Medicare covers your hospital and outpatient care no matter where you live. Medicare does not cover long-term care. It will not pay the rent for assisted living or memory care. Those facilities can run $3,000 to $10,000 a month depending on where you are, and some memory-care rooms run higher than that. Long-term care is a separate plan that needs its own answer, whether that's a long-term care insurance policy, a Medicaid spend-down worked out with an estate planning attorney, or a private-pay plan built with a financial professional.

Still Working at 65  

If you work for an employer with 20 or more employees and you have creditable group coverage, Medicare is secondary and you can delay Part B without penalty. If the employer has fewer than 20 employees, Medicare is primary, and you should sign up at 65 or risk large surprise medical bills. When employer coverage ends, you have eight months to add Part B and 63 days to add Part D drug coverage without triggering a penalty.

Why the Free Help Is Actually Free  

The reason most people try to do Medicare alone is that they assume asking for help means paying for help. It doesn't. Independent Medicare brokers work the same way an auto or homeowner's insurance broker works. You don't write them a check. They get paid by whichever carrier you eventually choose. The choice you make is the same one you would have made on your own, made with someone who has watched thousands of people make the same decision and knows what the mail is going to look like two years in.

What matters more than the enrollment itself is who you can call two years later when a bill shows up in the mail, a specialist leaves the network, or a prescription needs a prior authorization. Danielle's advice: choose a broker who's been doing this for a decade or more, with a team that can support you on the back end.

Boomer Benefits also runs a free Medicare 101 webinar and a Medicare Q&A Facebook group where the team answers questions all year long. Danielle wrote 10 Costly Medicare Mistakes You Can't Afford to Make ($2.99 on Kindle, $10 in paperback) because her team kept seeing the same errors from people coming into Medicare.

FAQ  

When should someone start learning about Medicare? Danielle recommends starting at 60 if you can, and no later than a year before your 65th birthday. Waiting until a few weeks before your birthday is often too late for the decisions that need to be made well.

Can Medicare be delayed if you're still working? Yes, if you have creditable coverage through a large employer (20 or more employees). No, if the employer has fewer than 20 employees.

What happens if you miss the six-month Medigap window? In most states, you'll have to answer health questions and can be declined for pre-existing conditions.

Does Medicare cover long-term care? No. That includes assisted living, nursing homes, and memory care. Plan for it separately.

Does using a Medicare broker cost anything? No. Brokers are paid by the carrier you eventually choose, the same way auto and homeowner's insurance brokers get paid.

Where to Start  

The single most useful hour you can spend before you turn 65 is with someone who has walked hundreds of people through Medicare and can tell you what the choices actually cost on the back end. Reading Danielle's book, watching the free Medicare 101 webinar at boomerbenefits.com, or calling an independent broker are all no-cost places to begin. Do it before your birthday, not after.

Want to take the next step on the retirement income side? Run your own numbers with the free WIYN calculator at brettblake.annuity.com, which takes about three minutes. Ready to talk it through? Book a Retirement Clarity Session with Brett. Not a sales call. Not a slide deck. Your numbers, not ours.

Worry Less. Live Longer.

About the host  

Brett A. Blake is the CEO of Annuity.com, Inc., based in Gilbert, Arizona, and host of Safe Money Radio. Before Annuity.com, he scaled a business from roughly $50 million to nearly $1 billion. He is not a financial advisor or a product specialist. He asks the questions listeners would ask if they had access to the right rooms.

About the guest  

Danielle Roberts is co-founder of Boomer Benefits, a national Medicare brokerage licensed in 49 states with a team of nearly 200 employees. She and her team have helped more than 100,000 people through their Medicare enrollment. She is a Forbes Finance Council member, a best-selling author, a National Social Security Advisor, and a frequent source for CNBC, Fox, CBS, Kiplinger, and MarketWatch. Her book, 10 Costly Medicare Mistakes You Can't Afford to Make, is available on Kindle for $2.99 and in paperback for $10.

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DISCLAIMER: Safe Money Radio is for educational purposes only and does not constitute investment, tax, legal, or Medicare-plan advice. Products discussed may not be appropriate for everyone. Medicare information shared in this episode is educational and is not connected with or endorsed by the U.S. government or the federal Medicare program. Guarantees are not government-backed or provided by Annuity.com, Inc. Annuity.com, Inc. (NPN 21086345) operates as Annuity.com Insurance Marketing (CA License No. 6013124) and Annuity.com Insurance Solutions (NY License No. LA-1860109). Boomer Benefits and Danielle Roberts are guests of the program. Annuity.com, Inc. is not affiliated with Boomer Benefits and does not offer or sell Medicare Advantage plans, Medicare supplement plans, or Medicare Part D drug plans.