SOMEONE POSTED THIS comment on a Facebook retirement-planning group that I follow: “My plan is based on my spouse and I living to 95 and 94 respectively. Our paid house is now worth about 900K. I am comfortable it will appreciate at 5% per year. The plan shows a 75% chance of success. If we sell the house at 85-84 and rent at a retirement community the success goes to 99%. We could cut back on expenses and that 75% chance would improve but why do that if I don’t need to?”

I suppose that,

HOW DID I GET financially to where I am today, 15 years into retirement? It’s a good question—one that’s taken me a lifetime to answer.

I’ve been fortunate in a way that’s nearly impossible for Americans today. I worked for one company for nearly 50 years and I accumulated a traditional pension based on that service. In addition, during my last few years on the job, I was eligible for stock options, restricted stock awards and enhanced bonuses.

DURING MY FINAL NINE years with the Coast Guard, I was involved in decisions regarding search-and-rescue operations. We were almost always working with imperfect information. For three of those nine years, I was responsible for all missions in one section of the Great Lakes and, in my last year, I made the final decision on when to suspend search-and-rescue operations in an even larger area.
To lower risk, we often assumed the worst, and threw copious operational resources at the situation.

I BEGAN MY CAREER at a small startup biotech company, only to realize the place had too much office politics, plus not enough credit was given for new discoveries. That was at odds with what I wanted, which was to be a research scientist focused on the basic principles underlying diseases.
Fortunately, I was offered a tenure-track academic position at a large medical school in Houston. I never looked back. Indeed, I consider myself one of the fortunate few who woke early each and every day to pursue their life’s passion.

WHEN I WAS IN COLLEGE, working toward a bachelor’s degree in music education, a friend’s dad told me about Vanguard Group. I’d never heard of Vanguard, and I had no idea what a mutual fund was.
I did some research on the firm and its founder, John Bogle, and read his book Bogle on Mutual Funds. Soon after, at age 19, I opened an IRA at Vanguard and thereafter contributed the maximum allowed every year.

I HAD MY SIGHTS SET on retiring at age 59. Not exactly FIRE—financial independence-retire early—but certainly a bit earlier than my peers, close friends and family. I wanted to seek new challenges after spending more than 25 years in academic research. Our financial plan was solid. My wife and I calculated we’d have more than enough retirement income.
But my plans were upended, first by the COVID-19 pandemic and then by two life-threatening health issues.

HERE’S SOMETHING that’ll surprise exactly zero readers: I’m a planner. Even though I haven’t yet fully retired, I’m already worrying about how short the active part of my retirement will be.
For this, I blame my fellow HumbleDollar writers, as well as those who post comments. Many folks who are active on the site are older than me, and they’ve given me a sneak peek at what lies ahead. One thing I’ve learned: At some point between age 75 and 80,

I’M THINKING ABOUT retirement—again. But this time, it isn’t my retirement, but rather my wife’s. I earn our family’s primary paycheck, so I’m usually the focus of our discussions when we sit down to scrutinize the numbers and comb through the calendar, looking for a date when we should each hang up our physical therapist’s goniometer.
Even though I earn the bigger income, my wife has diligently worked just as long as I have,

LIKE MANY OF MY generation, I grew up in a family that never talked about money. I had some sense that I should save, but no sense of where to save. This made me susceptible to a lot of advice—both good and bad—that shaped my financial journey.
I married a teacher and I became a school-based speech pathologist. I knew we’d never be rich, but we would have a comfortable life. In those early days,

I READ QUITE OFTEN on HumbleDollar about the trials and tribulations of those planning for retirement—questions like when to retire, where to retire, what will my expenses be, when to take Social Security, how to minimize taxes, how much money to save, how much to spend.

I approached retirement quite differently. Even I’ll admit I’m not typical, and perhaps only questionably normal. I tend to set major long-term goals with modest attention to details.

MY HUSBAND WAS STILL working at age 65 when he went into heart failure. After heart surgery, he wanted to return to his job as the warranty administrator at a large New Jersey auto dealership. But we worried that the commute would be too taxing. He traveled 55 miles each way to and from his job, and it could take hours and be treacherous when the weather was bad. When additional complications ensued from the surgery,

HOW MUCH OF YOUR retirement planning revolves around your kids and grandkids? Your estate planning goals probably include bequeathing a meaningful sum. Perhaps moving closer to your kids and grandkids is part of your plan. Whether you consciously think about it or not, you may be counting on your children to help out if needed during your final years. That seemed to be my father’s plan.
But what if you don’t have kids? How different would your retirement plan look?

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,