Richard Connor

WE OFTEN PREPARE our taxes, only to learn we owe a substantial sum to Uncle Sam. Most of us believe we can’t do much about this—and yet there’s one simple fix available to many taxpayers: Make a tax-deductible retirement account contribution this year for 2019.
Indeed, thanks to the stock market’s decline, this is a great time to shovel more money into your retirement accounts—and you may discover you can add to more than one account.

WHEN MY YOUNGEST son graduated college, he had two solid job offers. One would have allowed him to live at home for free and the other was halfway across the country. Guess which one he picked?
In fairness, the job far from home was more interesting to him and provided a great start to his career. I remember him sitting down with his mother and me, and telling us he was planning to move to Texas.

NONE OF US WANTS to contemplate our own mortality. But we all need to think about it—including thinking about life insurance.
I was lucky enough to have a long tenure with a large company that provided term insurance at reasonable prices. My employer provided two times our salary in coverage and we had the option to purchase additional coverage equal to eight times salary. I was also able to buy insurance on my wife’s life equal to three times my salary.

ONE OF MY FAVORITE movies of recent years was Hidden Figures. There’s a pivotal scene where the hero, Katherine Johnson, realizes they need to use an ancient numerical technique known as Euler’s Method to solve the trajectory equations for John Glenn’s mission. This involves breaking a complex problem into very small pieces, solving each part, and then summing them to get the solution.
Over my engineering career, I used various numerical integration techniques to solve complicated problems.

FROM AN EARLY AGE, I was amazed at the power of mathematics to model our world and solve real world problems. In engineering school, we studied a host of mathematical techniques that did just that. But I wish we’d spent more time on probability and statistics.
In 1989, I read a book that gave me a broader view of how probabilistic our world is and, at the same time, made me aware of how ill-prepared the general population is to understand these concepts.

I’M A BIG FAN OF health savings accounts, or HSAs. They’re becoming more popular as a way to pay for medical costs—and, in the right circumstances, they can also be a valuable addition to your retirement plan.
What’s so great about HSAs? If used properly, they’re triple tax-favored. You get a tax deduction when you deposit funds. The growth thereafter is tax-deferred. And if you use distributions to pay for qualified medical expenses, withdrawals are tax-free.

IT’S THAT TIME of the year—when we should all reevaluate how much we’re saving in our employer’s 401(k). The 2020 contribution limit is $19,500, up $500 from 2019’s level. For those age 50 and older, the catchup contribution was also raised by $500, to $6,500, so these folks can invest as much as $26,000 in 2020.
In addition, it’s a good time to check we’re getting the most out of our 401(k). What are the rules on the employer match?

MY WIFE AND I SPENT Thanksgiving on the Outer Banks of North Carolina. For 25 straight years, we’ve gathered there with my wife’s extended family to spend the week of Thanksgiving at the beach.
It started with about 15 of us in 1994, all in a seven-bedroom house. Over the years, the family—and the size of the house—have grown significantly. This year, we had 39 in attendance, representing four generations. For the past five years,

FALL IS MY FAVORITE time of year, but there used to be one thing I dreaded: picking a health plan for the year ahead.
Many folks don’t know how to evaluate their health insurance options. I used to be in that group—until I adopted a fairly straightforward process. Bear with me while I walk you through the sort of choice you might face as an employee. The same analysis can be used if you’re buying insurance on your own.

WHEN I WAS IN THE workforce, it was easy to give to charity. Now that I’m semi-retired, it seems like more of a struggle—for four reasons:

Because I’m no longer employed fulltime, I can’t donate through payroll deduction, which used to make giving simple and automatic.
Leaving fulltime employment often results in reduced or uncertain income, and sometimes both. Today, I find it harder to know how much I can afford to give.
Retirement heightens thoughts of leaving a legacy to children and other heirs.

SHORTLY AFTER I retired in March 2017, I was asked to consult on some projects. I knew it was going to be a more complex tax year than I’d faced before. I had earned income from my previous employer, pension income and self-employment income from my consulting.
On top of all that, my wife started a new fulltime job the Monday after I retired. We switched to her benefits, but her company didn’t have a high-deductible health plan with an HSA,

A DECADE AGO, a large financial firm ran a clever advertising campaign that showed people going about their everyday lives carrying a bright orange six- or seven-figure sum that represented their number—how much money they needed to retire. It was clever because we humans like to simplify—and sometimes oversimplify—complicated issues. It’s one of our cognitive biases.
I spent almost 40 years in aerospace engineering. I did a lot of detailed engineering analyses, calculating expected performance numbers,

I’M ONE OF THOSE lucky folks whose employer had a traditional defined benefit pension plan. I worked in the aerospace industry, starting with GE in the 1980s. Various mergers led to us to become part of Lockheed Martin. Through these multiple sales and mergers, our benefits and pension plan stayed largely the same, though—to be honest—I didn’t pay a lot of attention in my early years and was only vaguely aware of the details.

MY FATHER-IN-LAW Jim was born in January 1927, the sixth of eight children, to an Irish-American couple in Philadelphia. During the Second World War, his three older brothers were in the armed services. That meant that Jim, barely age 16, had to quit high school and enter the work world, so he could earn an adult’s wage. His salary must have been critical to the family’s economic stability.
Jim’s brother Bill was killed in an accident at sea during ship maintenance in 1944,

FOR MUCH OF MY adult life, my view of financial planning was similar to that of many others: Simply put, financial planning equaled investment management.
I spent my career in aerospace engineering, surrounded by highly educated, mathematically competent colleagues. I was lucky enough to span the transition from defined benefit pension plans to defined contribution plans. My colleagues and I closely followed the market’s performance, our own company’s shares and emerging tech stocks. Some of the more mathematically inclined dabbled in options.