Late Fee
James McGlynn | Nov 11, 2019
I’M JUST A FEW YEARS from age 65—and being eligible for Medicare. One of my concerns: making a mistake that could trigger penalties. If you file for Social Security before age 65, you’ll be automatically enrolled in Medicare Part A and B. What if you’re still working at 65? Ask your human resources department for advice. Your coverage at work will dictate whether you should file for Medicare. If you aren’t covered by an employer’s health insurance plan and you aren’t yet collecting Social Security benefits, the best time to file for Medicare is three months before you turn age 65. That’ll allow time for the paperwork to be processed—and coverage should begin on the first day of the month you celebrate your 65th birthday. If you wait until age 65 to file, you might not have coverage for another month or so. What if you wait too long? There’s a penalty period that begins three months after you reach age 65. If it’s been more than three months since the month you turned 65 and you haven’t signed up for Medicare Part B, your monthly Part B premium will increase 10% for each full 12-month period that you could have been enrolled in Medicare Part B, but weren’t. You’ll pay this penalty for the rest of your life. There’s a similar penalty for Medicare’s Part D prescription drug coverage, but that penalty is calculated at 1% per month. It’s also permanent. These penalties are an inducement not to wait until you’re sick to get coverage and start paying Medicare premiums. The other penalty is potentially triggered if you’re stashing money in a health savings account (HSA) before you’re on Medicare Part A. HSAs, which offer unsurpassed tax advantages, are often funded by those with high-deductible health plans. But you aren’t…
Read more » Still Stretching
James McGlynn | Jan 25, 2022
THE SECURE ACT, which took effect Jan. 1, 2020, made inheriting an IRA even more complicated. Before 2020, beneficiaries typically had the option of taking distributions from an inherited IRA over their lifetime, potentially squeezing many more years of tax-favored growth from these accounts. The SECURE Act drew a new line, eliminating some beneficiaries’ ability to make use of the so-called stretch IRA. Beneficiaries now are divided into two groups. Some have to empty an inherited IRA within 10 years of the original owner’s death. Others are permitted to stretch out their withdrawals for longer, often over their estimated lifetimes. I want to focus on this second group—called eligible designated beneficiaries—who can still defer taxable distributions for longer than 10 years. It includes more people than you might think. Under the SECURE Act, eligible designated beneficiaries include: Surviving spouses Disabled individuals Chronically ill individuals Minor children of the IRA owner Individuals who are less than 10 years younger than the IRA owner. Surviving spouses continue to have the most flexibility because they’re allowed either to roll over an inherited IRA into their own IRA account, and potentially delay all withdrawals until age 72, or to leave the money in the inherited IRA. The key advantage: Spouses have the flexibility to either stretch withdrawals over their own life expectancy or over the deceased account holder’s “life expectancy,” as calculated by the IRS, which could be beneficial if that happens to be longer. Disabled and chronically ill individuals can also stretch withdrawals over either their life expectancy or the remaining life expectancy of the deceased. Unlike a spouse, however, they aren’t allowed to roll over the IRA into their own account. Instead, they must use an inherited IRA account to shelter assets until they’re withdrawn. Minor children of the IRA owner—but not…
Read more » The Taxman Cometh
James McGlynn | Oct 23, 2020
LATE LAST YEAR, Congress voted to kill off the so-called stretch IRA, which had allowed those who inherited retirement accounts to draw them down slowly over their lifetime. Many folks were surprised by the stretch IRA’s demise, but they shouldn’t have been. When a tax break or some other government provision benefits only a few folks, Congress often changes the law. Think back to 2015. That year, Congress eliminated the ability to “file and suspend” Social Security—another strategy that tended to be exploited only by a privileged few. I suspect we’ll see similar Congressional action in the years ahead. This election season, there’s been talk of reversing the tax rate reductions in 2017’s Tax Cuts and Jobs Act (TCJA), especially for those who’ve benefited the most from those cuts. In any case, after year-end 2025, many of the TCJA changes sunset. The upshot: If Congress doesn’t act in the next five years, taxes will automatically increase. But it isn’t just the TCJA that’s in the political crosshairs. Here are five other key areas where we might see changes to the tax code: There’s discussion of eliminating the preferential long-term capital gains and qualified dividend tax rates for those with incomes above $1 million. Warren Buffett has often complained that he pays a lower tax rate than his secretary. This change would ease his conscience by boosting the capital gains and dividend tax rate from 20% to potentially 39.6%, but only for those with seven-figure incomes. The TCJA reduced corporate tax rates from 35% to 21%. There are proposals to increase that rate to 28% and to ensure all corporations pay a 15% minimum tax. I predict that, at some point between now and 2034, there’ll be changes to the payroll tax that funds Social Security or, alternatively, that other federal…
Read more » Danger: Cliff Ahead
James McGlynn | Jan 29, 2020
MEET IRMAA. YOU WON'T like her. IRMAA is short for income-related monthly adjustment amount. It’s a premium surcharge levied on those covered by Medicare Part B and Part D—and who have income above certain thresholds. In 2020, the standard premium for Part B, which covers outpatient care, is $144.60 a month. That’s what you pay if you file taxes as a single individual and your modified adjusted gross income is $87,000 or less, or if you’re married filing jointly with annual income of $174,000 and below. What if your income, including tax-free municipal bond interest, exceeds these levels? You may be subject to the IRMAA surcharge. The Part B premium is set so that it pays for 25% of Medicare’s actual cost. The remaining 75% is effectively subsidized by the federal government’s general revenue. The IRMAA surcharge is designed to remove this subsidy for those able to pay—those whose income is above the $87,000 and $174,000 thresholds. The IRMAA surcharge only affects 5% of Medicare recipients, but—depending on what happens with the inflation adjustments to the IRMAA income brackets—this 5% could increase over time. In 2020, there are five different IRMAA income tiers. The Part B surcharge starts at $57.80 per month, equal to $693.60 annually, and gets as high up as $347 per month, or $4,164 annually. Keep in mind that the IRMAA surcharge is per person, so couples pay double these amounts. If your income bumps you into the next income tier, you trigger the new tier’s full surcharge. For instance, income that moves you into the second tier—which starts at $109,000, versus $87,000 for the first tier—will trigger the second tier’s higher rate, even if you exceed the threshold by just $1. This so-called cliff penalty means that $1 of extra income triggers an additional IRMAA surcharge…
Read more » John Oliver does a complete show skewering Medicare Advantage
James McGlynn CFA RICP® | Oct 31, 2025
<iframe width="560" height="315" src="https://www.youtube.com/embed/Ejoi9yfLVCc?si=e_gSARLaTFOHhSZh" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" referrerpolicy="strict-origin-when-cross-origin" allowfullscreen></iframe> Educational and funny
Read more » Your 10-Year Reward
James McGlynn | Jul 7, 2020
IF YOU’RE MARRIED, filing for Social Security can be confusing. But there’s one group who has it even worse—those who are divorced. In recent weeks, I’ve had a number of conversations with women who had no idea that they were even eligible for spousal benefits based on their ex-husband’s earnings record. (I also recently watched the television show Dirty John: The Betty Broderick Story, which gave completely erroneous advice on benefits for ex-spouses.) My hope: Someone reading this may learn that he or she is eligible for spousal or survivor benefits from an ex-spouse. A divorced spouse is eligible for Social Security spousal benefits if he or she was married for 10 years or more. Period. Being married for only nine-and-a-half years doesn’t cut it. Every divorce lawyer in the country should be aware that it’s worth delaying a divorce, so the marriage officially lasts at least 10 years. There are other mistakes and misconceptions among those who are divorced. The ex-spouse isn’t informed that you’re filing. The ex-spouse can’t prevent you from filing. As long as you’ve been divorced for more than two years, you’re aged 62 or older and your ex-spouse is at least age 62, you would be eligible for Social Security spousal benefits, as long as the marriage lasted 10-plus years. There are also misconceptions about when to file for spousal benefits. Unlike filing for Social Security benefits based on your own earnings record, where it often pays to delay to age 70, there’s no advantage to delaying spousal benefits beyond your full retirement age, which is age 66 or 67, depending on the year you were born. If you’re planning to receive only spousal benefits, because the benefit based on your own earnings record is modest, you shouldn’t wait to age 70, but rather file…
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Deeply Rooted
ArticleMark Crothers | May 23, 2026
Mark Crothers is a retired small business owner from the UK with a keen interest in personal finance and simple living. Married to his high school sweetheart, with daughters and grandchildren, he knows the importance of building a secure financial future. With an aversion to social media, he prefers to spend his time on his main passions: reading, scratch cooking, racket sports, and hiking.
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