WHEN WE’RE YOUNG, WE simplistically view our family’s money journey as one long road with clear signs that tell us to “speed up,” “change lanes” or “get off.” It’s only later, as we gain wisdom, that we can discern how messy the journey is—and how each of us ended up turning onto a different street to pursue financial freedom in our own unique way.
By exploring the money stories of three family members, I have come to better understand my own financial journey.

I GOT OUT OF THE ARMY in August 1969. In the months prior, my wife and I discussed our financial plans. Simply put, if I was given a raise to $160 a week when I returned to work, we could buy some furniture for our small apartment. Bingo—we made it. I was earning $8,300 a year.

The other part of our plan was to save my wife’s salary toward a house down payment. She left the job market for good the following July,

I WROTE MY ESSAY for My Money Journey 14 months ago. Since then, our family’s journey has continued apace—including rethinking where we live.
The highlight of the past 14 months was the addition of another grandchild. We now have four grandsons, ranging in age from five months to 10 years old. Last summer, our younger son and his wife purchased a home in Monmouth County, New Jersey, roughly an 80-minute drive north of us.

THIS IS MY FIRST article for HumbleDollar. I’m new to the site, but not new to writing for the public and, indeed, I’ve contributed regular columns to some small newspapers.
My life has had more twists and turns than going down a Kentucky country back road filled with hillbillies, of which I am one. Kentucky is either the poorest state in the country or next to it by any measure you want to look at.

I DON’T TRACK MY finances that closely and I don’t make big financial moves very often. Partly, it’s because I’m so busy with other things. But partly, it’s because I’ve come to see the virtue in benign neglect.
Still, this is shaping up to be a surprisingly busy year. I’ve taken a handful of financial steps—with three key goals in mind:
No. 1: Prepaying retirement. Like many others as they approach retirement,

I WAS AT WORK WHEN my daughter called. “Grandpa was taken to the hospital in an ambulance, and you need to meet Mom and Grandma there as soon as you can.”
I entered the hospital room 45 minutes later, and I saw my mom in tears standing next to my dad’s lifeless body. Dad’s hair and face were spotted with wood chips and dirt, and he was wearing a torn flannel shirt and old blue jeans.

IT WAS PROBABLY THE last time I would see my brother. I’m 78 and ravaged by a chronic but controlled cancer, a stroke warning and a stent. Rich is 74, with a health profile only a little less foreboding. Both of our parents died at 81.
Always cordial but not always close, we’ve worked through his resentment about how I abdicated my role as an older brother and my jealousy about his close relationship with our explosive father.

HAVE YOU THOUGHT about what made you the person you are—the way you think about money, life, your behaviors, your likes and dislikes? When I look at my own life, I can clearly see the impact of my childhood.

My mother and grandmother made a lot of my and my sister’s clothes. I recall those paper dress patterns all over the apartment. Is that why I dislike shopping for clothes? I’m happy to let my wife and daughter decide what I should wear.

IN SOME FAMILIES, adult siblings work together to take care of their aging parents. But many times, one adult child ends up doing most, if not all, of the work—which is how things have played out in my family.
I’m the oldest sibling, and my wife and I took on the task of caring for my octogenarian mother and stepfather after they moved to Georgia from Colorado in 2017. I have a brother and stepbrother who live in other states.

HI RYAN, DON’T FREAK out because I’ve written an actual letter rather than an email. No big news here, no emergency, we’re fine. I just have something that’s been percolating and I want to share it with you.
Ry, it’s become clear learning about investing is not where you’re at right now. I’ve tried to think of what I might have done to turn you off. We know I was depressed and withdrawn for much of your childhood,

MY MONEY JOURNEY began as a young girl when a confluence of events created tragedy and financial ruin for my family. I grew up in Brooklyn in the 1950s. After the death of my father at age 40, we lost our home and had only the barest of necessities.

At that time, there was little help for people in our situation. The meager government benefits that existed were highly regulated and came with a lot of intrusion into your personal life.

I STEP INTO THE OLD farmhouse where I grew up and am momentarily confused.

Where’s the blue sofa under the living room bay window with its plump pillows and cozy blankets that my mother likes to throw over her as she reads the morning paper? Where’s the coffee table with the covered pewter candy dish filled with M&Ms and Hershey Kisses? Where’s the rickety table where our family of eight crowded around for countless meals in the tiny but somehow adequate kitchen?

IN FALL 2021, I WROTE about my father-in-law’s impending death due to cancer. He died a few months after publication. I had the honor of writing his obituary. Like my wife and her family, I have found myself wanting to call him many times since he died.
I was born in the early 1980s. That means that, until very recently, all I’ve known is a falling interest rate environment. People from my father-in-law’s generation knew environments like today—when interest rates and inflation rose together,

ON DEC. 14, MY WIFE and I celebrated 54 years of marriage—not bad for a curmudgeon and the person who’s had to live with him.
Considering that the average marriage in the U.S. lasts seven to eight years and the divorce rate is near 50%, we’ve done pretty well. On top of that, we got married just 10 months after our first date—and I was in the Army for eight of them. I remember receiving a letter from my dad while I was in the Army in which he basically asked,

I BOUGHT AND SENT 16 Christmas cards this year. Why spend $6.99 for the box of cards and $9.60 for stamps? I frequently communicate with most of the recipients via email and texts—but that’s why the cards are special.
Apparently, many other Americans feel the same way. Billions of cards are still bought and presumably sent each year, despite the cost of postage, according to the Greeting Card Association.
I could send virtual cards.