The One Annual Review That Protects Your Retirement Budget

Every year, Medicare health and drug plans can change things like costs, coverage, provider networks, and pharmacies. 

That means a plan that worked great last year may suddenly be:

Medicare Open Enrollment: October 15 to December 7 (changes start January 1). 

And if you’re already in Medicare Advantage, there’s also a limited extra window:

Medicare Advantage Open Enrollment: January 1 to March 31 (for people already enrolled in a Medicare Advantage plan). 

Why this matters: Most people don’t compare plans during open enrollment—KFF reports 69% didn’t compare options in a recent period. 

So they stay on autopilot… and autopilot can get expensive.

Crazy Tip: You don’t need hours. You need 30 minutes once a year to confirm your doctors + your medications still make sense in your plan.

If you own a home, many states and local areas offer senior-focused programs like:

Nearly all states have some form of senior property tax relief program. 

But here’s the catch: many programs require you to apply, and deadlines vary by location. 

Property taxes are a monthly cash flow. If you miss the window, you may be paying more than necessary until the next application cycle.

Crazy Tip: Call your county assessor or use reputable guides like AARP’s property tax resources to find your local homestead exemption / senior exemption rules and deadlines. 

If you’re collecting Social Security before full retirement age and you still work (even part-time), there’s a yearly earnings test limit.

For 2026, the Social Security Administration states:

This isn’t about fear. It’s about timing.

A quick yearly check helps you avoid surprises and plan smarter.

Crazy Tip: If you’re not sure when to claim or how work affects benefits, use the Social Security Quick Calculator as a starting point. 

Many people assume: “Same meds, same plan, same cost.”

But prescription coverage can change because plans can change formularies, pricing, and rules from year to year. 

This is exactly why Medicare open enrollment exists—to review your Part D prescription drug plan or Medicare Advantage plan drug coverage. 

Crazy Tip: Review your meds list once a year in the Medicare Plan Finder and confirm:

After age 50, U.S. retirement rules allow catch-up contributions so older adults can save more in tax-advantaged accounts. That opportunity is use-it-this-year-or-lose-it.

For 2026, the IRS announced:

Crazy Tip: Even if you can’t max it out, set an automatic contribution. Catch-up rules exist because many people don’t get serious about saving until later—and that’s normal.

With care,

Mike Bridges

Founder, The O55 Report