The Biggest Medicare Mistakes to Avoid

After years of helping San Diego County residents navigate Medicare, Ashley Watson has seen the same costly mistakes come up again and again. Most of them are completely avoidable — but only if you know to look out for them. Here are the ones that matter most.

Mistake #1: Missing the Enrollment Deadline

Medicare's Initial Enrollment Period is a 7-month window around your 65th birthday. Miss it — even by a single day — and you may face a permanent late enrollment penalty on your Part B premium (10% for every 12-month period you were eligible but didn't enroll). That penalty follows you for the rest of your life.

The fix: Know your enrollment window and mark it on your calendar. If you're still working with employer coverage at 65, make sure you understand whether you qualify for a Special Enrollment Period before assuming you can wait.

Mistake #2: Thinking Your Current Doctors Are Covered — Without Checking

This is one of the most emotionally painful Medicare mistakes Ashley sees in San Diego. A client enrolls in a Medicare Advantage plan without verifying their doctor is in-network — and then discovers their longtime physician doesn't accept the plan.

The fix: Before enrolling in any Medicare Advantage plan, verify that your specific doctors — primary care, specialists, and any hospitals you prefer — are in the plan's network. Ashley does this as a standard part of every consultation.

Mistake #3: Choosing a Plan Based Only on the Premium

A $0 premium plan sounds great, but it isn't always the most cost-effective choice. If a plan has high copays, a large deductible, or doesn't cover your medications, your actual out-of-pocket costs throughout the year can far exceed what you'd have paid on a slightly higher-premium plan.

The fix: Look at total cost of ownership — premiums, deductibles, copays, and drug costs — based on the healthcare you actually use. Ashley helps clients run these numbers so the comparison is real, not just the sticker price.

Mistake #4: Not Comparing Part D Plans Based on Your Actual Medications

Each Part D prescription drug plan has its own formulary — the list of drugs it covers, and at what tier (cost). Two plans with identical premiums can have wildly different out-of-pocket costs for the same prescription. Choosing the wrong one can cost hundreds of dollars a year.

The fix: Use Medicare's Plan Finder tool at Medicare.gov and enter your exact medications. Or let Ashley do it for you — she compares Part D plans based on your specific drug list every time.

Mistake #5: Ignoring the Annual Enrollment Period

Medicare plans change every year. Premiums go up. Formularies change. Provider networks shift. A plan that was perfect for you last year may not be the best fit this year — but many Medicare enrollees never review their coverage and end up overpaying or underinsured without realizing it.

The fix: Every fall (October 15 – December 7), review your plan for the coming year. Ashley contacts her clients proactively each year to do exactly this — it's part of the service she provides at no extra cost.

Mistake #6: Waiting Too Long to Switch to a Medigap Plan

When you first enroll in Medicare Part B, you have a 6-month Medigap Open Enrollment Period during which insurance companies must accept you for any Medigap plan — regardless of health history. Once that window closes, you may need to pass medical underwriting to get a Supplement plan, and you could be denied or charged more based on pre-existing conditions.

The fix: If a Medicare Supplement plan fits your situation, enroll during your Medigap Open Enrollment Period. If you've already missed it, a broker can still help you explore your options, but your choices may be more limited.

Mistake #7: Using a Broker Who Only Represents One Carrier

A "captive" agent works for a single insurance company and can only sell you that company's plans. An independent broker like Ashley represents dozens of carriers and can compare across all of them. You'll always get a more complete picture — and a more honest recommendation — from an independent broker.

Avoid Every One of These — For Free

Ashley Watson is a licensed, independent Medicare broker serving all of San Diego County. A single free consultation can help you avoid all seven of these mistakes. Book your free consultation or call (619) 947-2325 — seven days a week.