Sam Olson Insurance Services

08/30/2026

08/27/2026

Retiree health coverage isn’t automatically the best option once you’re eligible for Medicare.

Sometimes keeping your retiree group plan makes perfect sense. Other times, you could be paying significantly more than necessary—or giving up benefits and flexibility available through Medicare.

The key is to actually compare the details:

✔️ Monthly premiums
✔️ Deductibles & copays
✔️ Prescription drug coverage
✔️ Provider networks
✔️ Medicare Supplement or Medicare Advantage alternatives
✔️ Coverage for a spouse or dependent

Don’t assume your retiree plan is the best choice just because your former employer offers it. Compare the numbers and understand your options before making a decision.

Retirement HealthInsurance MedicareSupplement MedicareAdvantage

08/26/2026

💊 Want to know what your prescription will actually cost on a Medicare Part D plan?

Medicare.gov makes it pretty easy — if you know where to look.

In this video, I walk through how to:
🔹 Look up your medication
🔹 Compare the cost across different Part D plans
🔹 See what you’ll pay at different pharmacies
🔹 Check your estimated cost throughout the year

And remember: the same medication can cost very different amounts depending on the Part D plan and pharmacy you choose.

Before enrolling in a drug plan, always run your prescriptions through Medicare.gov. The plan with the lowest monthly premium isn’t necessarily the plan with the lowest total cost.

📌 Save this video so you can reference it during your next Medicare plan review.

Medicare101 MedicareEducation

08/24/2026

⚠️ Think COBRA means you can delay Medicare? Think again. Unfortunately, COBRA generally does not protect you from Medicare late-enrollment rules the same way active employer coverage can.

That misunderstanding can potentially result in:

❌ Late enrollment penalties
❌ Gaps in coverage
❌ Delayed access to Medicare
❌ Unexpected medical bills

If you’re approaching 65 and leaving employer coverage, don’t automatically assume COBRA is the best bridge.

Before electing COBRA, make sure you understand how it interacts with Medicare.

📲 Have questions about your Medicare transition? Send me a message.

RetirementPlanning MedicareInsurance MedicareHelp HealthInsurance

06/02/2026

05/08/2026

You may not need to wait to change your Medicare plans