IT’S TIME TO THROW out our broken retirement system and start over. My first article for HumbleDollar, published more than five years ago, was titled Choosing Badly. It was about the inability of most employees to make good use of their 401(k) plan.

Guess what? Nothing’s changed.

Today, some 401(k) plans still have too few investment choices, while others have too many. There are multiple options that people don’t understand, such as target-date funds compared with index funds,

IT WAS JULY 2003. My wife and I were in our early 50s. We had jobs we liked and we lived comfortably. Our two children were about to go to college, and we had a plan for covering the cost. We had renewed our marriage vows on our 25th anniversary. We had no debt.
But I began thinking.
What would our financial situation be if we retired and our only income was Social Security? That was entirely possible.

MY WIFE AND I ARE super-savers. For us, that means we save as much as permitted each year in the retirement plans available to us. Once we’ve done that, we invest in our regular taxable accounts, where there’s no limit on the amount we can contribute.
We’re under age 50. That meant that, in 2022, the maximum contribution was $6,000 each to our IRAs and $20,500 each to our 401(k)s. Because the contribution limits increase with inflation,

THE SUMMER AFTER MY sophomore year at Virginia Tech, I had an internship with Frito-Lay, working in its computer applications department at the company’s research headquarters in Irving, Texas. One of the programs I had to learn was VisiCalc, the first spreadsheet program for personal computers. This was my introduction to spreadsheets, and I’ve been hooked ever since.
Sometimes, I joke with my family that I live the data-driven life—not to be confused with Rick Warren’s purpose-driven life.

BEFORE I RETIRED TWO years ago, my first thought—as a software engineer—was to come up with a detailed project plan. But that proved too difficult. Instead, I decided to settle on some tenets to guide my retirement.
To aid in my thinking, I listened to podcasts and bought books. The usual list of prerequisites for a successful retirement were clear: financial means, good health and a robust social network.
I worried most about the last item.

A LOT HAS BEEN written, here at HumbleDollar and elsewhere, about the “when” of retirement. Not surprisingly, there are strong opinions.
For example, I’m a member of a Facebook group where the overwhelming consensus is, “Don’t work one single day longer than you absolutely have to.” Of course, many people don’t have the luxury of choosing their ideal retirement date because life intervenes: They get let go from their job or experience health issues that dictate the answer to the “when” question.

MY WIFE AND I DROVE back from Arizona in June, so we could spend the summer months here in Minnesota. We took a longer but more scenic route through Utah and Colorado, and saw many natural wonders, including several national parks and the Rocky Mountains.
How did we spend our “windshield time”? Knowing we had an upcoming meeting with our financial planner, we discussed our work and our finances, along with when it might make sense for each of us to retire.

MY COMPANY SHIFTED in the early 2000s from a traditional defined benefit pension plan, with a formula based on salary and years of service, to a cash-balance pension plan. All new employees would be put in the cash-balance plan. Existing employees had a choice to stay in the traditional plan or move to the new plan.
A generous transition credit for the cash-balance option was offered to current employees. The transition credit was based on a combination of current salary,

I HAVE TROUBLE accepting things at face value. I like to validate information, checking it against several sources. This is especially true when it comes to all things money- and retirement-related. But it’s not always easy to do.

Do Americans tell the truth about how they spend their money? Do they actually know? Does it really take extreme frugality to save for the future, a talent many folks lack or refuse to embrace?

I look around and,

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,

IT TOOK FIVE FALSE starts to write this column. Each time, I’d inundate readers with information. So, here’s a sixth try.
Have you ever seen those questions to financial advisors on the internet that say, “I have [insert dollar amount]. Can I retire?”
How the heck could the advisor give a reasonable response? To answer the question, it takes more than simply knowing how much you have in the bank. You need a lot of personal and financial information to make the decision to retire.

I NEVER PLANNED TO retire at age 53. I wasn’t an early adopter of the FIRE, or financial independence-retire early, philosophy. In fact, I didn’t start saving seriously until my late 30s, when I left my first husband and finally realized that—unlike pensions in my native U.K.—my U.S. pension didn’t come with an annual cost-of-living adjustment.

Instead, three developments in the late 1990s led me to consider quitting. First, I was no longer enjoying my job.

AS FOLKS HURTLE toward retirement, they often wonder whether they’ve saved enough, debate when to claim Social Security and fret about how they’d pay for long-term care. Make no mistake: Such issues are hugely important.
But amid these financial musings, we should also spare a thought for four other questions:
How can I transform myself from a diligent saver to a happy spender? This sounds so easy, and yet many struggle with it,

AS A FIRST-YEAR dental school student in 1999, when I was debating whether to apply for a military health-professions scholarship, I never gave a thought to receiving a military pension. In fact, I don’t even recall knowing that was a possibility.
I was already in debt to the tune of $65,000 from my undergraduate degree, so I was simply seeking financial aid for dental school, typically considered the most costly type of graduate education a person can buy—more so even than medical and law school.

WHAT’S THE BEST DAY of the year to retire? Many people think it’s Dec. 31. But I used to think my ideal retirement date would be the day in February when the Cleveland Guardians played their first spring training baseball game. What better way to start my retirement than seeing my childhood baseball team in Arizona get ready for the upcoming season? When I wasn’t watching baseball, I could visit the Grand Canyon and Sedona.