John Yeigh

SOON AFTER GRADUATING college and starting work, I visited a dentist I found in the Yellow Pages for a long overdue teeth cleaning and exam. Although I had never had a cavity, the dentist informed me that I had multiple cavities that urgently needed to be filled. Naïve me allowed this dentist to fill the two supposed cavities of most concern.
Somewhat traumatized, I avoided dentists for a time. Finally, I queried several older coworkers,

TED BENNA IS OFTEN called the “father of the 401(k).” In 1980, he implemented the first 401(k) plan based on his somewhat bold interpretation of the Revenue Act of 1978. He certainly couldn’t have envisioned the $11.4 trillion in “defined contribution” 401(k) and 403(b) accounts that we have today.
Individual retirement accounts also took off in the early 1980s, and traditional IRAs now hold an additional $11.3 trillion. Combined, that’s an impressive $23 trillion in tax-deferred retirement assets.

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. 

“YOU WILL ROTH!”
“But Dad, I’m only 10.”
“Evan, it is never too early to start saving. Besides, this gives you 70-plus years of compounding.”
“Yes, Dad, but didn’t you tell me last week that I need a job and earned income to contribute to a Roth?”
“We can arrange to get you a paycheck. I’ll get a friend or neighbor to hire you. What would you like to do?”
“I like to play soccer.”
“Evan,

EXPERTS OFTEN ARGUE that tax-avoidance strategies shouldn’t drive our financial plans, especially as Congress is forever fiddling with the tax rules. And yet many of us end up making decisions based on federal tax policy, which is loaded with incentives designed to change behavior and advance social goals.
That’s certainly true for my wife and me. Despite the tax code’s many provisions—and its 75,000 pages of complexity—four big-picture tax considerations have largely shaped how our financial lives have turned out,

LET ME PLAY THE contrarian. A dominant narrative today is that—compared to earlier generations—younger workers are both economically disadvantaged and less inclined to do anything about it.
Such notions have been bandied about for at least 2,000 years. Horace wrote that “the beardless youth… does not foresee what is useful, squandering his money.” For a more modern take, check out these comments from HumbleDollar contributors and readers lamenting the financial plight of today’s younger generation:

Company “loyalty to employees in large measure no longer exists.”
“Young people are forced to contend with the twin challenges of relatively low salaries and high student loan burdens.”
Baby boomers are “fortunate in a way that’s nearly impossible for Americans today.”
“Many workers are strapped today,

I’VE FOUND RETIREMENT to be a conundrum. We finally have the time to pursue any activity we want in a leisurely manner—spend time with family and friends, exercise, sleep, travel, read, binge watch TV, knock items off our bucket list. On the other hand, I now hear the constant ticking of life’s clock.
Tick tock, tick tock.
For the decades before retiring, life for my wife and me was pedal-to-the-metal with work, children, commuting and chores,

KEY PROVISIONS IN 2017’s Tax Cuts and Jobs Act (TCJA) will expire in 2026 unless Congress steps in. That means folks have a two-year window to prepare.
What’s at stake? Income-tax rates will increase for many taxpayers. This creates an incentive to boost income over the next few years by, say, undertaking Roth conversions to shrink traditional retirement accounts and thereby lowering future required minimum distributions.
The sunsetting of key TCJA provisions would also cut the threshold for federal estate taxes in half,

TODAY IS THE 50th anniversary of the most important day of my life. On Feb. 16, 1974, I met my wife. Choosing a life partner is arguably the most crucial decision we make. No other choice likely matters as much, including education, career, finances, where we live or even having children.
We’ve all heard the statistic that half of marriages end in divorce. In addition, marriage rates are declining, marriages are happening at later ages,

WHEN WE UPDATED our wills last year, my wife and I attempted to cover every imaginable scenario, including the future state of our children’s marriages, grandchildren, step-grandchildren and the like. Still, we and our lawyer missed one outlier scenario: What if our whole family was wiped out simultaneously? Think airplane or car crash.
This risk crossed my mind when our small family took a flight together for a recent vacation. Our core family is just six people: us and our two children,

MY WIFE AND I JUST finished watching the Netflix documentary Live to 100, which I highly recommend. The four-part series focuses on Dan Buettner’s study of pockets of people around the world who achieve amazing longevity, including many residents who live to age 100 and beyond.
The seven longevity locations include Okinawa, Japan; Sardinia, Italy; Ikaria, Greece; Nicoya, Costa Rica; and Loma Linda, California. These locations of long-lived people have been labeled “blue zones” based on the seminal demographic work on Sardinia by Giovanni Mario Pes,

ONE RECENT TREND among newly minted retirees: unretirement. According to an AARP study, some 3% of retirees are back in the workforce one year later, taking on either fulltime or part-time jobs. Often, unretiring wasn’t part of the retiree’s original plan—but we shouldn’t assume it’s necessarily about needing money.
Starbucks’s Howard Schultz, quarterback Tom Brady and Disney’s Bob Iger are poster children for unretiring. Even our HumbleDollar world includes many examples of those who have reinvented,

THE DOUBLE-DIGIT recovery by the S&P 500-stock index this year has been driven almost entirely by seven mega-cap stocks: Apple, Google, Microsoft, Amazon, Meta, Tesla and Nvidia. In fact, these seven stocks now comprise more than 25% of the index.
Since our family is heavily invested in a mix of the S&P 500, U.S. technology and growth funds, plus some individual tech stocks, I began to worry about our portfolio’s investment concentration. I tallied our positions in these seven stocks across all our accounts.

MY DAYS WRITING for HumbleDollar may be numbered. I recently started playing with Google’s Bard, OpenAI’s ChatGPT and Microsoft’s version of the ChatGPT artificial intelligence (AI) platform, and was curious to see how they might perform in providing basic financial guidance. Their answers were generally sensible and aligned with HumbleDollar’s approach—though also occasionally flawed.
You might think that AI can’t possibly replace articles penned by contributors, since the charm of HumbleDollar is the contributors’ personal stories.

IF YOU’RE IN YOUR 60s or older and making sizable Roth conversions, it isn’t just income taxes that you need to worry about. You may also trigger much higher Medicare Part B and Part D premiums.
We’re talking here about those Medicare surcharges known as IRMAA, short for income-related monthly adjustment amount. These surcharges are over and above 2023’s standard $1,979 per person Medicare premium, and they’re based on income from two years earlier.

IN AN EFFORT TO identify the simplest, most resilient lifetime investment portfolio, author and investment analyst Chris Pedersen concluded that a minimum of two funds is required. His recent book, 2 Funds for Life, summarizes his back-testing study to find a simple yet effective portfolio. The book is available free at PaulMerriman.com.
Pedersen found that a 90% allocation to a Vanguard Group target-date fund coupled with a 10% allocation to a small-cap value fund provides meaningful diversification across stocks and bonds,

IN MY ONGOING EFFORT to reduce our accumulated stuff, I was trolling through our collection of old thumb drives to see what I should download, save or toss. Among them, I discovered the 258-page presentation from a two-day retirement course that my old employer sponsored in 2006.
I wondered how the advice had—17 years on—stood the test of time. As I reviewed it, I found some excellent suggestions and some that were lacking, though I hesitate to fault the presentation’s authors.

JEFF BEZOS ONCE asked Warren Buffett why everyone doesn’t just copy his example when investing. Buffett famously replied, “Because nobody wants to get rich slowly.”
The magic of saving diligently, coupled with decades of compounding inside tax-advantaged accounts, can ensure financial freedom. In fact, young married couples today have an outside chance of accumulating $10 million by the time they reach the new required minimum distribution age of 75.
To reach the $10 million jackpot,

WHAT DO BEN FRANKLIN, Charles Darwin and David Cassidy all have in common? All have advised us not to waste life’s precious time.
Almost everything about money translates into time. Money can buy us time—either more free time or more time spent on higher-value activities. Money can purchase a nicer house or car, a luxury vacation, greater financial support for our children, fun toys or experiences, reduced financial stress—and, eventually, a comfortable retirement. The financial independence-retire early,

AS IF WE DIDN’T already have enough evidence, here’s further proof that stock market predictions have little value: A year ago, 24 highly regarded stock market pundits forecasted that the S&P 500 would close out 2022 at 4,904, according to data posted by CNBC’s Brian Sullivan. That 4,904 was the average, with their predictions ranging from a low of 4,400 to a high of 5,330. The S&P 500’s actual 2022 close was 3,840.
Meanwhile,

THE TWO SECURE ACTS—2019’s and 2022’s—may inadvertently increase the federal and state tax rates on tax-deferred retirement accounts, such as 401(k)s, 403(b)s and IRAs. While well-intentioned, the laws result in required withdrawals being bunched into fewer years—which could push people into higher tax brackets. But there are ways this tax toll might be lightened or avoided, as you’ll see.
With tax-deferred accounts, the normal advice is to delay taxable distributions for as long as possible to give more time for investment growth.

THREE YEARS AGO, I wrote an article suggesting I had 7,000 days to go, at least according to the Social Security Administration’s life expectancy calculator. The 1,000 days since then represented a significant 14% share of my remaining actuarial life.
The good news is, the Social Security calculator now estimates that my life expectancy is about 6,400 days. I’ve enjoyed 1,000 days of life but only used up 600 days of life expectancy. That’s like a 40% return on life over the past three years.

OVER THE PAST FEW weeks, my wife and I did something we hadn’t done in four years: We bought bonds.
Specifically, we parked some money in one- to two-year Treasurys paying 4.3% to 4.6%—the highest rates in 15 years. Our portfolio now approaches 5% bonds, and we plan to buy more. We’re waiting to capture higher rates following the expected Federal Reserve rate increases.
Bonds represent a seismic shift for us. In early 2020,

IN MY FIRST ARTICLE for HumbleDollar nearly four years ago, I said I’d claim Social Security benefits at my full retirement age of 66 and two months. By claiming mid-way between 62 and 70, I intended to hedge my bets, because I couldn’t know such relevant variables as my lifespan or future tax rates, inflation rates and investment returns.
And I did indeed claim Social Security recently, though—full disclosure—it was nine months after my full retirement age.

THE WILLS, POWERS of attorney and advance directives drawn up for my wife and me were drafted according to the laws of another state—and were badly out-of-date.
For example, these various documents included guardianships for our then-young children, with a trust to make gradual payouts until they turned age 35. Both our children have since graduated college, become professionally employed and demonstrated they’re financially responsible.
Despite all that, I’m embarrassed to admit that we procrastinated over getting new wills.

IN AN EARLIER ARTICLE, I noted that my savings journey began in 1960 with a couple of jars of pennies that I started collecting at age five. I was following family ancestor Ben Franklin’s maxim that “a penny saved is a penny earned.”
One of my uncles also had an interest in coin collecting. He and I began to actively search through countless penny rolls to find pennies with dates that we didn’t have.

NEW HAMPSHIRE’S STATE motto is “live free or die.” But for my wife and me, the first part might be better expressed as “live tax-free.”
We just moved to New Hampshire from Maryland. The move’s main purpose is to be near our kids, enjoy lake and mountain activities, and experience cooler summers. But New Hampshire’s zero tax rate on earned income, pensions and capital gains is a major bonus.
Eight states have no tax on personal income,

WE NEEDED MONEY to close on a new home. The mortgage process progressed smoothly—until the underwriters suddenly rejected the property right before closing. To get together the money needed to close, my wife and I had to resort to loan sharks—ourselves.
We borrowed from our IRAs. The rules allow tax-free distributions for either a 60-day rollover to a new IRA or reinvestment back into the same IRA. When we called Vanguard Group to execute our “rollovers,” the phone reps were well-versed on this short-term,

I LEARNED A LOT about finance and life from my uncle. He was an early investment advisor and published a book on wealth management. Even though he was not a registered investment advisor or a Certified Financial Planner, our family proudly extolled his ideas when I was growing up.
My family first introduced me to my uncle’s doctrines when I was a child of five or six. I had been given a small piggybank to store my life’s savings.

I’M DEBATING whether my life is better described by Tom Cochrane’s Life Is a Highway or Eddie Rabbitt’s Driving My Life Away. In a recent article, I noted that our family has driven our cars about 1.9 million miles. Since I’m the family’s King of the Road, I’ve been along for at least two-thirds of that ride.
I’m also, alas, the king of lost time.
The average commuting speed in the Washington,

IN HINDSIGHT, MY WIFE and I made a mistake by over-saving in tax-deferred accounts. It’s not that we saved too much overall. Rather, we ended up with retirement savings that aren’t diversified among different account types. In fairness, this was caused by the limitations of our work-sponsored retirement plans, coupled with the stock market’s handsome appreciation in recent years.
The classic approach is to build a three-legged stool for retirement—Social Security, a pension if available,

THIS PAST YEAR marked my 50th anniversary of driving. Over that time, our family has owned 19 cars and driven them roughly 1.9 million miles. While latte purchases frequently evoke financial debate, cars seem less discussed, despite being Americans’ second-largest expenditure after housing. The purchase, ownership, maintenance and sale of cars can all get pretty complicated.
Cars are considered a depreciating asset, but not always. My first car was a 1967 Mercury Comet, which I bought for $400 in 1973.

A 2021 SURVEY by the Employee Benefit Research Institute found that three-quarters of retirees said the value of their financial assets was the same or higher than when they first retired. This finding was consistent from the poorest respondents to those with the most wealth. The typical time in retirement for the respondents was seven to 10 years.
One implication: Retirees may be underspending their accumulated wealth. EBRI examined five reasons for this possible underspending:

Saving assets for unforeseen costs later in retirement
Don’t feel spending down assets is necessary
Want to leave as much as possible to heirs
Feel better if account balances remain high
Fear of running out of money

The first two reasons—”saving for tomorrow” and “no current need to spend”—were reported by almost half of respondents.

INTEREST RATES HAVE been low for years, with 10-year Treasury notes now yielding some 1.4%. How about dividend-paying stocks instead? Many pay twice what Treasurys currently yield, though obviously with more risk. My strategy: Instead of a classic 60% stock-40% bond mix, I’ve landed at roughly 70% stocks, with another 15% to 25% in individual stocks against which I’ve written call options.
By selling call options, I give the buyers the right to purchase the underlying stock from me at a specified price—the so-called strike price—at any time between now and when the options expire.

ONE WAY TO MAXIMIZE long-term family wealth is through a teenager’s summer or after-school job. How do these small paychecks add up to serious money? Probably the best investment we can make for our children and grandchildren: Stash their earnings in a Roth IRA.
A teenager’s Roth has three things going for it: little or zero taxes owed on the small bits of income earned, 70 or 80 years of investment compounding, and zero taxes owed when those gains are withdrawn.

SOME FAMILY MEMBERS recently asked me to help them find a financial advisor. As luck would have it, soon after, Barron’s published a perfectly timed article, “America’s Best RIA Firms,” which listed 100 highly ranked registered investment advisors (RIAs). Similar lists are available from CNBC and the Financial Times.
It was time for me to get to work. Who wouldn’t want to recommend a “top” firm to his or her family?

IN RECENT WEEKS, my wife and I have seen scheduled activities for the next few months come crashing down. Two long-planned vacations with friends, our various volunteer work and our son’s college semester have all been cancelled.
It appears we’ll be effectively quarantined at home for the next two or three months. That means plenty of time to worry about—and work on—our investment portfolio. But it’s also a great chance to bring greater order to our household assets:

Every year,

IN EIGHT YEARS, my wife and I will be age 72—and we’ll be locked into required minimum distributions from our retirement accounts for the rest of our lives. Nearly all of our savings are in tax-deferred accounts.
At that juncture, we’ll also have begun Social Security payments. The upshot: Our tax rate will jump significantly and, thanks to the combination of required minimum distributions (RMDs) and Social Security, our income will easily exceed our expenses.

CNBC ANCHOR BECKY Quick recently summed up today’s retirement investing dilemma in one sentence: “You’re never going to make enough money if you have 40% of your money in bonds.” She, along with many pundits, believe the old standby recommendation to invest 60% in stocks and 40% in bonds—the classic balanced portfolio—is dead. Google “60/40 asset allocation” and the majority of recent articles have titles that include such words as “eulogy,” “endangered,” “dead,” “the end of” and “not good enough.”
Likewise,

I HAVE NEVER BROKEN a New Year’s resolution—because, until this year, I’ve never made one. But now that I’m retired, with time on my hands, I figure my wife and I ought to challenge ourselves with 10 financial resolutions for 2020:

We’ll continually monitor routine spending with the goal of reducing or eliminating at least half-a-dozen expenses this year. That’s one every two months. Phone companies, internet providers and insurers, be warned: Here we come.

TAX-DEFERRED ACCOUNTS are great, until they aren’t—when we have to pay taxes on our withdrawals. Millions of Americans have tax-deferred accounts, pundits laud them, companies help fund them, institutions service them and markets help them grow. But when it comes time to empty them, often the only person to guide us is Uncle Sam, who’s patiently awaiting his cut.
Efficiently managing 30 years of retirement withdrawals from a 401(k), 403(b), IRA or other tax-deferred account is just as important as the 40 years of accumulation.

SAVE FIRST FOR THE kids’ college or for your own retirement? Pundits generally recommend that parents put themselves first. But I’d argue the question demands a more nuanced answer. The tax code offers numerous tax-savings opportunities for families with dependent children—and those tax breaks shouldn’t be overlooked.
To be sure, for cash-strapped parents, the top two financial priorities should be building up an emergency fund and putting at least enough in their 401(k) or 403(b) to capture the full employer match.

MY LAST CLOSE relative—other than my kids—recently experienced major health issues. That prompted me to reflect on my own potential longevity. I’ve got 7,000 days to go, more or less, or at least that’s what the Social Security Administration’s life expectancy calculator tells me.
It seems like a big number, but it’s less than 20 years and just a quarter of a U.S. male’s average 29,000-day lifespan. Each day in retirement, we get to decide how to utilize one of those precious remaining days—whether to use it wisely or possibly fritter it away.

WE HIT THE RENOVATION snooze button for years. We were put off by the hassle and the expense, plus we were concerned that as little as 50% of a remodeling project’s cost ends up reflected in a home’s value—and that assumes you sell within a year. On top of that, we rented out our house for three years, making renovations difficult.
The watershed moment: My wife indicated—very firmly—that she was through putting out pots and bowls to catch all the drips inside our house every time a heavy rain occurred.

WE ARE ALL VICTIMS of continually rising costs. Here’s the oft-repeated drill: The service provider sends the yearly renewal bill by mail or email, or the new annual cost is simply posted to our credit card account or deducted from our bank account.
Assuming we even notice the charge, the head-scratching starts. What the heck was the cost last year anyway? The new fee may have increased just 3% or 5%, which doesn’t seem like a lot.

STOCK MARKET INDEXES are at all-time highs, share prices are expensive relative to earnings and global economic growth is slowing. Is it time to consider rebalancing our portfolios and perhaps adopting a more defensive approach?
If you believe in rebalancing—maintaining a relatively consistent allocation to stocks and bonds—then, at some point in this bull market, you must sell stocks. I am hugely hesitant to do so, for three reasons. First, I am fundamentally a buy-and-hold forever investor,

THE CLASH, THE U.K. punk-rock group, famously asked, “Should I stay or should I go?” Retirees and job changers need to tackle the same question when they leave their employer.
At that juncture, you have four options for your 401(k) or 403(b) account: You can leave the balance in your old employer’s plan, roll over the balance to a new employer’s plan, roll over the balance to an IRA or close out the account.

EMPLOYEES WHO accumulate significant company stock can end up with a problem, though not necessarily a bad one: concentrated stock holdings. When these employees retire, their challenge is to sell those shares in a way that maximizes their value—taking into account the share price, dividends and taxes. One strategy: Utilize covered calls.
Selling a concentrated stock position can take many years because of tax considerations or restrictions on selling. For example, if appreciated shares are held in a regular taxable account,

MY WIFE AND I TAKE some over-the-top precautions to protect our financial accounts. Why? After 40 years of working, our life’s savings boil down to digits stored on computers. No one anymore holds stock and bond certificates, stuffs money in mattresses or buries gold in the backyard. The integrity of those digits is all important.
Here are our 11 strategies—which go way beyond the normal account and password protection recommendations:

We only deal with major institutions.

WHILE FINANCES ARE critically important to retirement, it wasn’t the biggest challenge that my wife and I faced. Instead, when I quit the workforce two years ago, a stranger moved into our house.
It was me.
For the prior two years, I had worked in Texas, while my family remained in Maryland, so my son could complete high school there. Even before my temporary Texas move, I worked longish hours, traveled overseas regularly and had lengthy daily commutes.

“YOU’RE FIRED” WAS made famous by Donald Trump as host of The Apprentice. Imagine my surprise when my broker delivered the same message to me two years ago.
In 2015, my job was transferred to Texas. I opted to become a long-distance commuter, while my family stayed in Maryland. Around that time, we moved homes, so our son could attend a better high school. In addition, I was helping to launch two huge long-term work projects.

STICKER SHOCK IS common when families begin the college search—with good reason. According to the U.S. Department of Education’s National Center for Education Statistics (NCES), inflation-adjusted college costs have more than doubled over the past 30 years.
Annual tuition, fees, room and board for fulltime undergraduate students at four-year colleges averaged $26,100 in 2015-16, the last year for which NCES data is available. That average drops to $22,400—if you include junior colleges. On the other hand,

THE NCAA BASKETBALL season concludes every year with the March Madness playoffs. Many Americans engage in bracketology—trying to figure out which teams will get knocked out in each round and which will advance. Warren Buffett even offers an annual bracket-picking challenge, where Berkshire employees can win $1 million a year for life.
This year, however, Americans with substantial retirement accounts might also want to try another form of bracketology: studying the 2017 tax law—and asking whether it offers a unique opportunity to convert hefty amounts of traditional IRA money to a Roth IRA.

WHO DOESN’T LIKE free money? I know I do. If you’ve worked for a major U.S. corporation, you have probably also been offered free money. But there’s a potential downside—in the form of a large, undiversified investment bet.
What am I talking about? Let’s start with the matching employer contribution that’s offered in about half of 401(k) plans. You put in a portion of every paycheck and your company then matches all or half of your contribution.

WE ARE A NATION obsessed with youth sports. Time magazine says it’s a $15 billion-a-year industry. As many as 60 million kids participate.
Sports are good for kids for all kinds of reasons: promoting exercise and a healthy lifestyle, enhancing team work and relationships, providing structure, instilling confidence to overcome challenges and delivering the joy of playing.
During our children’s sports journeys, we parents are often led to believe that our little sports stars are on the path to the holy grail—a full athletic college scholarship.

WE’VE ALL GOT STUFF. Too much stuff. George Carlin was among the first to highlight our obsession with stuff in his 1980s standup comedy routines. I hadn’t thought much about Carlin or stuff for decades—until 2015, when I inherited my parents’ stuff.
Not only did I inherit their stuff, I inherited some of their parents’ stuff and their grandparents’ stuff. Boxes, drawers and shelves full of unlabeled stuff. I wouldn’t call my parents hoarders.

AFTER THE MARKET turbulence of recent months, the idea of a 100% stock portfolio would strike many folks as crazy. Yet, when I was in the workforce, that’s pretty much what I owned.
I never felt my all-stock portfolio was particularly risky. My wife and I had solid paychecks to rely on. We always maxed out our retirement plans, while also adding to other accounts, and then lived on whatever remained.
While the stock market’s volatility and the occasional downturns may have been disconcerting,

WHEN OUR DAUGHTER landed a great job after her 2018 college graduation, we expected her to soon move off the family payroll. She immediately budgeted to take on all routine living expenses, including housing, food, car and utilities. We did volunteer to cover some smaller expenses, largely in situations where family plans are available, such as cellphones, Netflix, Amazon Prime and AAA. We also kept her on our employer-provided health insurance, which involved no added cost.

I WAS SINGLE-TRACK mountain biking with two friends. We had stopped for a rest—which was when I discovered how completely wrong I’d been with most of my financial decisions.
We had all recently retired from the same company and were debating when to claim Social Security. One buddy stated that he planned to start at age 70, so he would receive the maximum monthly payment possible. He defended his position by arguing that he was in good health,