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5 Pitfalls to Avoid as You Approach Medicare Age

5 Pitfalls to Avoid as You Approach Medicare Age

September 05, 2026

As you approach age 65, it’s common to be inundated with communication about your Medicare options. It can be difficult to decipher facts from fiction and packages from policies that are right for you.

Take it from someone who’s been where you are, it is possible to sort through the Medicare maze with clarity and confidence. However, there are several common pitfalls of which you should be aware.

  1. Don’t miss your window. Your initial enrollment period starts three months before you turn 65 and lasts three months after. If you miss this seven-month window, you might have to wait to sign up, and penalties increase the longer you wait. It’s important to note that this is not a one-time late fee; it’s charged for as long as you have that type of coverage—for most people that’s a lifetime penalty! Consult medicare.gov for more details on how to avoid late enrollment penalties.
  2. Evaluate your coverage options carefully. The Medicare health and drug plan that’s right for you will depend on your health conditions, prescriptions, and existing private insurance. Be sure to consider all your sources of healthcare coverage before selecting the right policy, and don’t forget to confirm that your preferred healthcare providers and medications are included in the plan network. While evaluating your options, don’t default to the cheapest premium. Look into the plan’s deductible, copay, and out-of-pocket maximums.
  3. Pay attention to income thresholds that increase your premium. Before wading through your Medicare plan options, many people with high incomes can trigger income-related monthly adjustment amount (IRMAA) increases for Medicare Part B and Part D. In 2026, if you make more than $109,000 as a single filer or $218,000 as a joint filer, you may be subject to higher premiums. Income thresholds are based on the modified adjusted gross income on your past two years’ tax returns and include both capital gains and Social Security benefits.
  4. Watch out for scams. Medicare will never unexpectedly contact you to request your Social Security number, bank details, or Medicare number. Medicare will also never pressure you to join a plan on the spot. If these things happen, it is more than likely a scam. Unfortunately, scammers have gotten more sophisticated over the years and can spoof official-looking phone numbers; it’s not safe to merely trust your phone’s caller-ID. If you’re unsure, hang up and call 1-800-MEDICARE independently to confirm.
  5. Don’t take advice from people who don’t know you. Signing up for Medicare can feel overwhelming. The marketing materials you receive and plans your friends and family use share a significant blind spot: they don’t apply to your unique situation. It’s important to consult professionals who are familiar with Medicare, are familiar with your circumstances, and have your best interest at heart.

Although Stewards Planning Group does not sell Medicare, we work closely with partners who do. I’ve personally been through the Medicare enrollment process and have guided many clients through the steps over the years. Healthcare costs are a sizable expense—particularly in your later years of life—and ensuring you have adequate coverage is a critical piece of your financial plan. 

If you’d like guidance from a Stewards Planning advisor or a referral to our Medicare partners, feel free to call our office.