Don Southworth

I FELL IN LOVE with baseball in 1965. My parents were in the midst of divorcing. I found sanctuary listening to San Francisco Giants’ games on the radio. I put on my batting helmet and pretended I was Willie Mays swinging at every pitch or diving on my bed catching imaginary lines drives. Willie had a magical year and, although the hated Dodgers nosed us out in the end, a lifelong passion was born.

WHEN YOU’VE BEEN saving and investing for a long time, you have a long list of things you wish you could do over. Like hanging on to Apple, instead of selling at $85 a share. Like buying an index fund, instead of that hot mutual fund that quickly turned cold. My wife calls these “what ifs.” We have a rule not to talk about them because they almost always lead to arguments about who was wrong.

I’M NOT SURE HOW anyone can achieve financial peace and prosperity without addressing the “b” word—budgeting.

I got my first credit card in my late teens. I bragged that—in my wallet—I had whatever my credit limit was and could do anything I wanted with it. By my early 20s, I was in credit-card debt. But as long as I could pay the monthly minimum, I didn’t think I had a problem. Of course, the interest rate was astronomically high—sadly,

THIRTY YEARS AGO, I took a course on sales and entrepreneurship. We had to buy a few books, subscribe to The Economist and The New York Times, and buy an HP 12C calculator. This was not your usual sales class. I felt like I was piloting the space shuttle as I learned how to use that HP calculator.
I’ll never forget the first time the instructor had us calculate how much money we’d need when we retired.

IT WAS A WARM MAY night in 1977. I was 19 years old and the manager of a fast-food restaurant. I was also in the middle of a five-year addiction to compulsive gambling that would eventually lead me to the brink of spiritual and financial bankruptcy. It was about 10:30 p.m. and I was cleaning up the store after closing. I was planning on going to the racetrack to catch the last race when I was done.

A FEW MONTHS AGO, I decided to join a neighborhood golf club. Although I started playing when I was a teenager, I’ve never been that good. Since the group invited players of all handicaps, I thought it would be a fun way to get some exercise and meet new people.
I realized on the first day that I was probably the youngest player. Despite my rustiness, I was putting for birdies on both of the first two holes.

MY MOM AND DAD split up when I was seven years old. Money was an issue for the rest of my childhood. Mom was rarely able to work fulltime and, according to her, child support and alimony were never enough.

When I started working a newspaper stand at age 12, I was expected to give 25% of my daily take for rent. Mom also demanded that I save at least 10%. Depending on the headlines,

ON NEW YEAR’S DAY 1994, life was looking pretty good. I was age 35 and, despite not having a college degree, was slowly climbing the corporate ladder. I’d just finished the most lucrative year of my career, and a semi-promotion promised to increase my income by 50% to 100%. My wife Kathleen was happily home-schooling our six- and 13-year-old boys, and we were thinking about buying a bigger house.

Then life happened.

On Jan.

COMMON WISDOM TELLS us that we all pay taxes and that we all die. As a semi-retired minister, financial coach and tax preparer, I’ve gained an unusual appreciation for these two certainties of life. But never more so than this year.

I began my first congregational ministry in August 2001, two weeks before the Sept. 11 terrorist attacks. The first class I offered was titled A Year to Live, in which we met over 12 months to plan and prepare as if we would die at the end of the year.