James McGlynn CFA RICP®

I HAD LUNCH RECENTLY with a longtime friend—a 66-year-old retiree. I asked him how he’s generating income since he hasn’t filed for Social Security and doesn’t have a pension.
He said that, for now, he’s just drawing down his savings. I know his wife is three years older and her lifetime earnings were much lower than his, so I asked him if she’d filed for Social Security. He proudly said that she hadn’t—because she expects to live to age 90,

I’M 64 AND PREPARING to sign up for Medicare next year. I’ve done extensive research, including earning the Retirement Income Certified Professional designation. I’ve also written articles for HumbleDollar on Medicare coverage, Medicare premiums, Medigap and health savings accounts.
In addition, I’ve befriended Medigap salespeople, advised others on which plans to choose, and asked those on Medicare for advice on their experience with the program. I feel as if I’ve been preparing to take the Medicare filing “exam,” and I’m excited to sign up.

RETIREMENT PLANNING is complex because there are so many topics to master. In my chapter for the HumbleDollar book My Money Journey, I organized those topics into four categories: guaranteed income, medical expenses, tax-free accounts and asset allocation. In the book, I went into more depth, but here’s my 10,000-foot view of each one:

Guaranteed income is reliable income that isn’t affected by changes in the stock and bond market,

FOR MOST SENIORS, purchasing Medicare Part D prescription drug insurance is the right move—even if they don’t require any expensive medicines right now. The coverage insures against the risk of someday needing prescription medication that costs thousands of dollars and might be otherwise unaffordable.

The federal government subsidizes Part D, so it’s cheaper than purchasing stand-alone private drug insurance. Another good reason to enroll in Part D at the first opportunity: You avoid the penalty associated with a late sign-up.

MANY COMMENTATORS worry about the stock market in October, a month associated with the crashes of 1929 and 1987. But I now pay more attention to March—especially March 10.
As an observer of the stock market since 1980, I stumbled upon an odd coincidence. Major financial events this century, like stock market peaks and troughs, have centered on the month of March. Here are four examples:
March 10, 2000: The Nasdaq peaked at 5048.

THE FEDERAL RESERVE raised the federal funds rate in 2022 from zero to more than 4% to combat high inflation. While those rate increases severely damaged the stock and bond markets, they made some financial products more attractive. In particular, there are three products that are more appealing now than they were a year ago: income annuities, long-term-care insurance and various interest-paying investments.
Like many people, to take advantage of low loan rates, I refinanced my home mortgage before 2022’s rising interest rates.

I’LL BE ENROLLING IN Medicare in a couple of years. I wish I knew how much my premiums will be, but that’s a mystery worthy of Sherlock Holmes. I’ve researched it thoroughly, as you shall see, and it all starts with something called IRMAA.
IRMAA is not the name of my seventh-grade crush. Instead, it stands for income-related monthly adjustment amount. It’s the premium surcharge that people with higher incomes pay for Medicare.
How much is the surcharge?

I RECENTLY LISTENED to a podcast during which the speakers lamented the death of a colleague who was in his 30s. They mentioned a GoFundMe campaign to assist his family, so I assume the deceased had no life insurance. According to LIMRA, which collects data on the life insurance industry, less than 50% of millennials have individual life insurance.
There are two major types of life insurance: term and whole life. Term insurance is intended to cover a specific period,

YOUR LIFE’S FINAL costly chapter may be paying for long-term care. Indeed, the odds of needing care if you’re age 65 or older are around 50%.
Two key questions: Will you need care for an extended period and how will you pay for it? If the duration is short—which it is for many seniors—paying probably won’t be much of a problem. But if long-term care is needed for many years, financial decisions today might protect the legacy you hope to bequeath decades from now.

I RECENTLY VISITED Eastern Europe, where I volunteered to teach English in Poland through an organization called Angloville. I received free room and board at a resort in exchange for conversing from breakfast through dinner with Polish adults who wanted to improve their English.
In addition to meeting Poles and being immersed in Polish culture, I used my free time to explore nearby countries. Planning a vacation abroad? Based on my recent trips to Poland,

I REMEMBER 40 YEARS ago listening to Salomon Brothers economist Henry Kaufman bemoaning government deficits and predicting higher interest rates as a result. We institutional investors would gather in a room to listen to his declarations through a “squawk box” intercom system—because conference calls weren’t yet a thing.
Federal Reserve Chair Paul Volcker was in the process of wringing inflation out of the financial system by raising the federal funds rate so high that investors would rather hold cash investments than spend money.

ONLINE SPORTS BETTING is currently legal in 30 states but eventually will be legal everywhere—because the tax revenue is simply too attractive. All this was made possible by the Supreme Court, which in 2018 struck down federal legislation prohibiting online sports betting.
The sports leagues spent decades denouncing gambling, saying it threatened the integrity of the game. But my concern isn’t the “integrity” of the game. Rather, I worry about the individual bettor who ends up wagering too much.

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.

AS THEY APPROACH retirement age, workers sometimes get to choose between a monthly pension and a lump-sum payout. It’s a choice I recently made—one I researched carefully. In the end, I made an unusual decision that took a few extra steps.
Let me start at the beginning. In 1984, I began working for American National Insurance Company as an investment analyst. I left the company in 1991, but still qualified for a small pension.

I HAD A NEW HOME built in 2017. I financed it with a 30-year mortgage at a 3.875% interest rate.
Early last year, when interest rates dropped due to the pandemic, I suggested that readers refinance. I took my own advice, replacing my 30-year loan with a 15-year mortgage at 2.99%. The cost of refinancing seemed well worth the reduction in my loan interest rate.
Two months ago, I saw that mortgage rates had continued to decline,

THIS IS THE LAST year that my income won’t affect my Medicare premiums.
At issue is IRMAA, or income-related monthly adjustment amount, which is the premium surcharge for Medicare Part B and Part D if you exceed certain income thresholds. The surcharge is based on your modified adjustment gross income from two years earlier. Like almost all retirees, I’ll begin Medicare at age 65. That means IRMAA will be based on my income for the tax year when I reach age 63,

NEWS OF ENTREPRENEUR Peter Thiel’s $5 billion Roth account, which was funded with PayPal stock, has motivated Congress to look at restricting the growth and size of Roth accounts.
There’s talk of limiting Roth account balances to $5 million or $10 million. There are also proposals to limit both backdoor IRA conversions and so-called mega-backdoor conversions. The latter involves funding a nondeductible 401(k) and then immediately converting the money to a Roth. There’s even discussion of not allowing high-income workers to convert traditional IRAs to Roth accounts.

AIRLINE TRAVEL during the pandemic can be frustrating. There’s mask-wearing on all trips, and COVID test results are required before boarding international flights. Then there’s the spate of last-minute cancellations, leaving passengers unhappily stranded at the gate.
On that score, Spirit Airlines has recently made headlines. I’ve also personally endured last-minute cancellations by British Airways and American Airlines. Even when you finally board a flight, many domestic airlines have suspended serving alcoholic beverages, except to first-class passengers.

IF YOU’RE MARRIED, it’s almost certain that one of you will outlive the other—perhaps by many years. What are the financial implications? Here are 10 issues to keep in mind:
1. Social Security. For a married couple, their Social Security benefits can consist of two workers’ benefits or a worker’s benefit and a spousal benefit. On the death of either spouse, the remaining benefit is the higher of the two benefits. For instance,

I HAD PLANNED a trip to Vietnam for 2020—which coincided with the start of the pandemic and got scratched. I naively rescheduled the trip for this summer. Unfortunately, countries that lack vaccines have been forced to lock down and keep out even vaccinated tourists like me, so that trip also got nixed.
Ever the optimist, I rescheduled for Europe in July. This time, it was the delta variant and changing travel restrictions that ended my third international trip before it even began.

LEAVING BEHIND full-time work leaves a void. How will you fill it? In my semi-retirement, I’ve found four communities.
I grew up in Fort Worth, Texas, but moved throughout my career. Fifteen years ago, I returned to Texas and—as part of my relocation—”pioneered” working from home. I’ve spent the past few years reconnecting with classmates from elementary school through high school, meeting them individually for lunch and using Facebook to arrange annual mini-reunions. I’ve known some of these folks for more than 55 years.

IT’S BEEN CALLED the stealth IRA. We’re talking here about health savings accounts, which offer a triple tax play. First, contributions are tax-deductible. Second, the accounts grow tax-deferred. Third, if the money is used to pay permitted medical expenses, there’s no tax on the sum withdrawn.
That might sound similar to an employer-sponsored flexible spending account for health care costs, but those are more restrictive. If much or all of the money isn’t spent by the end of the year,

MANY FOLKS ARE do-it-yourselfers when it comes to home improvement projects. On that score, I have no skills, so I end up paying others. In fact, in high school, I was so anxious to avoid metal shop and woodshop that I opted for typing and four semesters of bookkeeping.
It’s a different story when it comes to my finances. Yes, I use an accountant to file my taxes. But helped by both a degree in finance and the Chartered Financial Analyst designation,

SPECIAL PURPOSE acquisition companies are hot. But will investors get burned?
Also known as “blank check” companies, special purpose acquisition companies (SPACs) are shell companies with no current business operations that raise investor funds through an initial public offering (IPO). The companies then seek a merger with a private company, allowing its new partner to go public without the delays and demands of a traditional IPO.
An additional advantage: The acquired companies are allowed to make projections about their business prospects,

RETIREMENT RULES seem to get revised almost every year. Whether it’s IRAs, Roth IRAs or Social Security, Congress is constantly rewriting the regulations.
Just think about what’s happened over the past half-a-dozen years. The Bipartisan Budget Act of 2015 eliminated the “file and suspend” option for Social Security recipients. Savvy financial planners would advise clients who had reached their full Social Security retirement age to file for benefits, so their husband or wife could receive spousal benefits.

INSPIRED BY THE TV series The Queen’s Gambit, many people suddenly want to master the game of chess. But I’m more interested in mastering the practical world of retirement gambits—and that means matching wits with Congress and the IRS.
During my working career, I saved money in taxable brokerage accounts, IRAs and 401(k)s, but never focused on Roth accounts. At age 55, having left my last employer, I had two things that compelled me to begin—time and reduced income.

IF YOU DESIGNATE beneficiaries for your retirement accounts, that’s usually a surefire way to pass those assets directly to your desired heirs without going through probate—but not always.
Because those beneficiary designations are so important, you should verify your choices every year in case there’s a change due to, say, marriage, birth, divorce or death. Especially marriage and divorce. Which brings me to a crucial issue: When dealing with IRA and 401(k) beneficiary designations,

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 BEGAN MY CAREER in investments as a junior analyst at a public endowment fund. It was 1980 and I’d just finished my last investment class at college, where I learned about Modern Portfolio Theory. Why, decades later, is it still called “Modern”?
The Dow Jones Industrial Average was below 1000, versus today’s 27000. Men wore suits in 100-degree Texas heat. We had individual offices. We researched companies by reading brokerage reports, talking to brokers and requesting annual reports from companies.

I WORKED IN THE investment department of three different insurance companies. But I never had any interest in buying a whole-life insurance policy. I knew term insurance was the best way to get the maximum death benefit for my premium dollars.
Instead, as a mutual fund manager, I was always more interested in investing in the stock market. (That said, I didn’t invest in the first mutual fund I managed. Why not? I didn’t want to pay the 7% “load”—the upfront sales commission.)
But my attitude toward whole-life insurance changed six years ago.

AS I PLAN MY retirement, I have the advantage of a strong background in finance. I worked for 35 years in the investment field, primarily managing mutual funds. Early on, I obtained the Chartered Financial Analyst designation, which helped immensely.
Six years ago, when I was age 55, I embarked on a journey to comprehend the myriad rules and strategies surrounding retirement. I studied to become an RICP—a Retirement Income Certified Professional. While the CFA was useful for investment management,

DELAYING SOCIAL Security until age 70 will get you the largest possible monthly benefit, and that’s the right strategy for many retirees. But what’s right for many folks won’t necessarily be right for you—and you may want to file at 62, the youngest possible age, so you maximize your total lifetime benefit.
If you’re single with no dependents, you should probably file at age 62 if you’re in poor health or your family doesn’t have great genes,

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.

FORCED TO SHELTER in place, I’ve used the time at home to organize my finances. I’d already read Marie Kondo’s Tidying Up. But I needed her new book, Joy at Work, to motivate me to organize my digital life. Sometimes, it helps to have a step-by-step guide to prod you to deal with such drudgery. Here are four tips I used to get myself organized:
1. Consolidate fixed costs.

REACHING AGE 65 is a financial relief for many folks—because they’re finally eligible for Medicare. But then disappointment often sets in.
Why? Medicare might cover just 80% of medical expenses, leaving the patient to handle the other 20%. How will you cover that 20%? The usual solution is to buy a Medigap policy. But there are so many choices that it can be overwhelming.
My goal today: Help you narrow that choice a little—by comparing two Medigap plans,

I FIRST STARTED managing mutual funds a few months before the 1987 stock market crash, and I’ve had to navigate a fair number of market declines since then. My advice: Instead of worrying about how far share prices will fall or how widely the coronavirus will spread, think about the opportunities. I spy four of them.
1. Buy the dip. If you have cash, you might slowly dollar-cost average into the market,

IF YOU’RE IN YOUR 70s or older and you are charitably inclined, it’s time to get acquainted with one of your best financial friends: the qualified charitable distribution, or QCD.
A QCD is a distribution that’s made directly from your IRA to an organization eligible to receive tax-deductible contributions. A QCD counts toward your annual required minimum distribution, or RMD. But unlike a regular RMD, the QCD won’t add to your taxable income for the year—a potentially huge advantage.

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.

FUNDING A ROTH—and enjoying tax-free growth—may not have been an option for many high-income baby boomers when they were working. But these folks can still get money into a Roth IRA by converting their traditional retirement accounts—and often there’s a great opportunity to do so if they retire early and find themselves in a lower tax bracket.
The first thing to know: Converting from traditional tax-deferred accounts to a Roth IRA will generate ordinary income equal to the taxable sum converted.

MEDICAL EXPENSES ARE a big worry for retirees—leading many to purchase supplemental insurance. But you need to think carefully about which Medigap policy you buy.
What does this insurance get you? Medicare Part B, which covers doctor’s visits and other outpatient care, typically only pays 80% of the expenses that retirees incur. To plug this and other coverage gaps, many folks buy a Medigap insurance plan. Want to keep your current doctors and not be restricted to the network of medical professionals offered in a Medicare Advantage plan,

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,

WHEN I STARTED working fulltime in 1980, there were very few retirement savings vehicles available to the average worker. I remember setting up my IRA and contributing the $2,000 annual maximum—at the time the only retirement account I could fund.
Today, by contrast, there’s a slew of retirement choices on offer. Where should those new to the workforce focus their dollars? If you have access to a 401(k) or similar retirement plan with an employer matching contribution,

YOU CAN THINK of retirement as having four phases. Want to make sure you make the right decisions at the right time? An age roadmap can help.
Phase No. 1 is the preretirement period beginning at age 55. Why start then? If you leave your employer after this age, you can access your 401(k) without the usual 10% tax penalty on retirement account withdrawals before age 59½. To have this option, keep your 401(k) at your old employer,

THE INSURANCE MARKET for long-term-care coverage has had a checkered history—and yet there’s an increasing need for LTC insurance among aging baby boomers. My advice: Forget the original standalone insurance products and instead focus on the new hybrid policies.
What went wrong with the original standalone products? They proved to be underpriced. With policyholders living longer, insurers found themselves paying out more than anticipated. Policyholders also didn’t drop their policies as often as insurers expected—and the low lapse rate meant insurance companies had less chance to book profits while incurring no LTC expenses.

WERE YOU BORN between 1950 and 1953, have been or are currently married, and haven’t yet filed for Social Security benefits? There’s a loophole you may want to take advantage of—before it disappears.
For couples, settling on the right strategy for claiming Social Security benefits is critically important, because it affects the size of each spouse’s benefit or spousal benefit, as well as the survivor benefit. But the payoff can be especially large for the group I’m discussing here—those born between 1950 and 1953.