WITH THE ADVANTAGE of advanced age and flawless hindsight, I now believe the three most important contributors to retirement prosperity are a robust savings rate, an aggressive allocation to stocks and funding tax-free accounts, both Roth and health savings accounts (HSAs).
What about other financial factors, such as the investments we pick, whether we buy income annuities, when we claim Social Security and what Medicare choices we make? These matter on the margin, but I don’t think they’re as crucial to a successful retirement.
I MAY NOT BE THE best source of retirement advice. After all, I’ve called myself semi-retired for a decade and yet, faced with a grim medical diagnosis, I continue to work far too hard. Moreover, even if I opt to fully retire—which is doubtful—cancer will likely ensure my retirement will be all too brief.
On the other hand, I do run a website devoted to retirement issues, and that means I spend a lot of time reading and thinking about the topic.
A RECENTLY RELEASED book titled How to Retire is a goldmine for those in or near retirement. For the book, Christine Benz—Morningstar’s director of personal finance and retirement planning—conducted interviews with 20 experts, covering every aspect of retirement.
The result is a valuable field guide for those tackling life after work. Below are seven insights I found particularly useful.
1. Social connections. When we think about retirement planning, most of us tend to think first about the numbers.
ONE SUMMER MORNING in 2023, my husband Warren and I had an ad hoc business meeting over bowls of cereal. He told me, “The pandemic really hurt my in-person speaker’s business. I’m not sure it’s ever going to come back.” Then I mentioned that my freelance-design income had also really slowed down, the result of a lack of marketing and enthusiasm on my part.
Neither of these was a newsflash. But that was the moment we realized this is what retirement looks like for a self-employed couple in their mid-60s.
I’VE DECIDED UPON MY retirement date: July 1, 2025. We just passed the one-year countdown point, so I thought I’d share some of my ideas and plans for my final year in the workforce.
This countdown idea, of course, isn’t original with me. Indeed, there are apps that you can put on your phone to count down the time until retirement. I was primarily inspired by a retirement blogger named Fritz Gilbert. He’s way more decisive than I am.
RETIREMENT BRINGS with it a host of questions. The No. 1 question: Do we have enough for a financially comfortable retirement?
It’s an issue that’s no longer relevant to me, but it’s certainly relevant to my wife Elaine and to almost all HumbleDollar readers. But that fundamental question is just the beginning.
There’s a host of other retirement questions we ought to ask ourselves—about whether we have the right investment mix, how we’ll spend our time,
WHAT DO WE MEAN BY an “enjoyable” retirement?
I suspect there are as many answers as there are retirees. But one thing remains a constant: the need for an adequate income. Given a choice, I don’t think many people would choose to live a frugal, barely financially sufficient retirement.
My father retired at age 66. I say “retired,” but the reality is one day the owner called him into the office and said he was no longer needed.
I HAVE A FRIEND—we’ll call him Dave—who retired from Wall Street perhaps eight years ago, when he was in his early 50s. Soon after, he designed a sailboat and had it built, and he’s been sailing around the world ever since. In fact, judging from his Instagram updates, Dave is now on his second or third self-designed boat. Or is it a yacht? I don’t know anything about sailing.
At this point, you may be sighing with envy.
I’VE OFTEN BEEN TOLD that I’m too direct. To me, “direct” means to focus on the facts, get to the point, eliminate the fluff, keep matters as simple as possible.
Guilty as charged.
Think of all the time wasted by fluff. After making something more complicated than necessary, somebody is ready to provide a solution to what may or may not be a problem. Fluff thrives on confusion. It can scare folks unnecessarily. Most Americans don’t know how to deal with financial fluff.
WHEN I WROTE ABOUT the Dow Jones Industrial Average reaching 35,000 in 2021, it’ll surprise few to hear that I—like the stock market—was euphoric. I’ll confess that in 2022, as stocks plunged, I felt silly for having written the article.
But here I am again, writing about the latest milestone for our old friend. After flirting with the number in mid-March, the Dow hit an intraday high topping 40,000 on May 16 for the first time in its history.
EVERY TIME I READ about the decline in traditional defined-benefit pension plans, and the rise and supposed failure of 401(k) plans, I get annoyed.
You’d think all Americans once had good pensions that provided a secure retirement. That isn’t—and never was—true. Barely half of American workers ever had a pension and many of those received little value from them because their job tenure was too short. Job tenure has long averaged some four years or so.
HAVE YOU HEARD THIS nonsense about Social Security? It’s nothing but a Ponzi scheme. The trust fund is just IOUs. My favorite: I’d rather invest the money I pay in Social Security taxes because I’d get better investment returns.
All three claims reflect a fundamental misunderstanding of Social Security and how it works. Social Security is insurance—a form of annuity, a type of pension, a social safety net. It isn’t an investment and shouldn’t be viewed that way.
WHEN I WAS YOUNG, I felt immortal. We all did. It’s natural and likely hardwired into our brains. Such feelings of immortality have an evolutionary advantage, encouraging us to take the risks necessary to succeed.
When I planned for retirement, the notion of immortality was front and center. I consider myself in excellent health. I eat right. I’m not overweight. I stay active. I have a close circle of friends and an active social community from which to draw strength.
A FEW MONTHS AGO, my wife and I were searching for an exciting diversion on a Saturday evening. It didn’t take long to agree on the perfect experience—logging onto SSA.gov to check out our estimated Social Security benefits.
What’s so thrilling about that? Like many people, Social Security will comprise a key component of our retirement income. Even now, those future funds exert a strong influence on our plans.
Background. I’ll turn age 62 this month and still work full-time.
DURING THE PANDEMIC, I started devoting more time to retirement planning. But I had more questions than answers. I called a friend who was a financial planner.
“Retirement planning is confusing,” I told him. “I have a lot of questions.”
He laughed and said, “The answer is money. What’s the question?”
While his answer was humorous, it reflected what most retirees already know: Money is crucial for a good retirement. While it isn’t the only thing you need for a happy retirement,