Retirement Planning

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...

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...

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 worked for 40 years, paid your FICA taxes, and finally retired. You assumed your Social Security check was yours. Then you get your tax bill. Not only is the IRS taking a cut of your benefits, but Medicare just sent a letter saying your premiums are doubling next year. Welcome...

A Roth conversion ladder can create a rolling source of Roth IRA principal before age 59½. It cannot pay next month's bills. Each taxable conversion has its own five-tax-year period. While you wait, your living expenses, health insurance, and conversion taxes must come from cash, taxable investments, Roth contribution basis,...

The best Roth conversion years before Medicare are not a fixed age range. The safer way to find your Roth conversion “Golden Window” is to count backward from the first calendar year you expect to pay Medicare premiums. Social Security generally uses tax information from two years before the...

A Roth conversion can be worth doing even if it causes higher Medicare IRMAA premiums. The mistake is treating IRMAA as an automatic veto instead of one more marginal cost of the conversion. Add the extra federal and state income tax, add the extra Medicare Part B and Part...

Delaying Social Security can create more room for Roth conversions before benefits begin. But it can also produce a larger taxable benefit later. Claiming at 62 can reduce that conversion room, yet it may lower withdrawals from other accounts. That is why IRMAA should be modeled as one cost...

The Roth IRA 5-year rule is not one universal clock. For most Roth IRA owners, there are two different five-year periods to understand: one determines when Roth IRA earnings can be part of a qualified distribution, and separate five-year periods can apply to each Roth conversion or certain rollover...