Health Insurance

Medicare open enrollment IRMAA planning starts now—the deadline is December 7th, 2026.It’s that time of year again. Your mailbox is full of Medicare Advantage flyers, and you have until December 7th to pick your Medicare Advantage plan for 2026. But here is the trap most retirees fall into: They think...

top of Tier 1 After 30 years in financial planning, I've seen the difference between clients who understand leverage and those who liquidate at the worst time. Most retirees' instinct is to sell stock when they need cash. But in 2026, that sale could trigger Medicare IRMAA surcharges on top...

You have probably spent years obsessing over Asset Allocation—how much stock vs. bond exposure you have. That is important for growth. But in retirement, there is a silent killer of wealth that allocation doesn't solve: Asset Location. Here is the reality I’ve seen in 25 years of financial planning: You...

You’ve spent decades saving, only to find out that Medicare has a "success penalty." It’s called IRMAA (Income-Related Monthly Adjustment Amount), and it is a cliff. Go one dollar over, and you pay the full surcharge. But there is a defensive move most retirees miss. Tax loss harvesting to...

If you are still working at 65, you do not automatically need Medicare Part B on your 65th birthday. You may be able to delay Part B without a late-enrollment penalty when you have a group health plan based on your current employment—or your spouse's current employment—and you later...

Federal retirees are not required to enroll in Medicare Part B to keep FEHB. Your FEHB coverage can continue without Part B. The harder question is whether paying the extra Part B premium buys enough lower cost-sharing, broader Medicare access, and financial predictability to justify the cost. For 2026, the...

If you are working past 65 and still contributing to a Health Savings Account, Medicare can reach backward and erase months you thought were HSA-eligible. The answer is not to automatically stop contributions seven months before retirement. The controlling date is the month your Medicare coverage actually begins. For premium-free...

You think your Social Security net benefit is statutorily guaranteed to never decrease? You’re wrong. While the "Hold Harmless" rule is designed to prevent Medicare premiums from eating up your cost-of-living raise, there is a statutory exclusion that most retirees don't see until January. If you trigger IRMAA (the Income-Related...

You’ve been generous your whole life. In retirement, you continue to support the charities you care about, writing a check for a few thousand dollars each year. You feel good about it, and you assume your generosity is at least giving you a bit of a break on your...

For retirees who are charitably inclined, there is no single greater tool for tax and Medicare premium savings than the Qualified Charitable Distribution (QCD). Yet, it remains one of the most misunderstood and underutilized strategies in retirement finance. This is what I saw in nearly 3 decades advising people....