THREE WEEKS AGO, I wrote about my plan for generating retirement income, including my intention to make a series of immediate fixed annuity purchases. Immediate annuities are a profoundly unpopular product, so I was surprised when the article generated a slew of questions from readers.
Perhaps that interest reflects today’s miserably low bond yields, which have left immediate annuities as one of the few ways to generate a safe and sizable income stream. Intrigued?

IT’S SCARY TO RETIRE with a pool of money, knowing how you handle it determines your financial security for the next 25 years or so. It must seem even scarier to everyday Americans who don’t think they can count on Social Security.
A recent Tweet caught my eye. It linked to an article about the problems with the so-called 4% rule. As you might recall, the 4% rule states that, if you withdraw 4% of your portfolio’s value in the first year of retirement and thereafter step up the dollar amount withdrawn with inflation,

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,

I’M PROBABLY A YEAR or two away from regularly tapping my portfolio for income. That prospect—coupled with this year’s market turmoil—has led me to tinker with my investment mix and ponder how I’ll generate cash once I’m retired. One surprising result: I have more in stocks today than I’ve had at any time in the past three years, and I’m thinking of increasing my allocation even further.
Since 2014, I’ve thought of myself as semi-retired.

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.

ARE YOU PLANNING to withdraw funds from your Roth IRA? If you aren’t careful, you could owe both taxes and penalties, even though you’ve already paid taxes on the money that went into the Roth. At issue: the IRS’s five-year rule. How do you sidestep its unpleasant consequences? Bear with me while I explain.
First, a word of caution: You don’t have to take distributions from your Roth IRA during your lifetime. Withdrawals are strictly up to you.

I LIKE TO THINK of myself today as a pretty savvy investor. But I wasn’t savvy when I started out. Despite attending business school and earning a master’s degree in computer science, I knew nothing about managing money or saving for retirement, so I initially made a number of blunders—but also one particularly lucky choice.
My first real job after college was in 1987, as a systems programmer for the University of North Carolina in Chapel Hill.

SHOULD YOU CONVERT your traditional IRA to a Roth IRA? Below, you’ll find five questions to help you decide. If you answer “yes” to the first three questions, you’re a good candidate for a Roth conversion. If you answer “yes” to all five questions, you’re an outstanding candidate.
Question No. 1: Are you taxed at lower rates today than you will be in future?
Roth conversions make sense if your federal and state tax rates today are below what they’ll likely be when you have to take required minimum distributions (RMDs) from your traditional IRA.

ALMOST EVERYBODY collects Social Security at some point in their life. But it seems like that’s the only thing we all have in common.
Why are there such stark differences of opinion regarding Social Security’s purpose and effectiveness? Why are so many Americans willing to believe that one administration or another stole the Social Security trust fund? Why is any effort to modify the program for future retirees immediately denounced as a cut in benefits?

FOR MOST PEOPLE, life insurance is purchased to protect their income in the event of an unexpected death. If you’re 35 years old, you potentially have 30 or more years of future earnings that your family would lose if you passed away, so having life insurance during these working years makes sense. But what happens once you reach retirement? Before canceling your policy, it’s important to assess your situation, because keeping the coverage might be the better choice.

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,

ONE OF MY GOALS for 2020: develop a plan for doing Roth IRA conversions over the next 10 years. Once the money is out of traditional IRAs and in a Roth, it’ll grow tax-free. Problem is, the conversion means taking a tax hit today.
So why am I interested? There are several reasons: lowering lifetime taxes for my wife and me, creating the flexibility to manage future tax bills and leaving a tax-free inheritance to our children.

RETIREMENT IS BEING rethought: Playing lots of tennis, golf or bridge, while living modestly so we don’t run out of money, might have been an acceptable plan when lives were shorter.
Now, the early go-go years of life’s “fourth quarter” can last two decades, especially if we retire early. A life of pure leisure may not be financially possible—and it might even be a bad idea mentally, emotionally and physically. As we look beyond the current uncertainty of the coronavirus,

THE SAGA IS FINALLY over—18 months and $50,000 later. That’s what my clever moving strategy cost, including taxes, interest, insurance, utilities and some maintenance on the house I hadn’t lived in for more than a year. My strategy was intended to lessen stress, but instead it did just the opposite.
This all started because our 1929 house became too much to cope with, the stairs became too much for my wife—and I resisted moving for too long.

DESPITE THE NEGATIVE press, long-term-care insurance can be a smart buy. In fact, policies can be affordable for those as old as age 79. But as with any financial product, it’s important to understand what you’re buying—and make sure it fits with your goals.
In my last article, I discussed how much money you might earmark for long-term-care (LTC) costs. Need insurance to hit your goal? Today, the two main products are “traditional policies” and “hybrid life and long-term-care policies.”
Both types of policy offer similar LTC benefits.