My Dad Played Chess

by Ben Jennings, Lead Advisor, CFP®

“The apple doesn't fall far from the tree.”
“The acorn and the oak.”
“Like father, like son.”


We know the aphorisms, but they aren't always true, are they?

If you know me, you may imagine you can guess what my father was like. I'm laughing, as that's probably not going to work.

Here’s what I mean: I earned two master's degrees and several professional designations while my dad didn't finish high school. I enjoy classical music and reading, whereas my dad liked honky-tonk and watching Big-Time Wrestling. I work as a financial planner, but my dad was always caught by surprise every six months when he got his normal recurring car insurance bill. I could go on, trust me.

As a child, I was the sort of kid my dad found challenging to understand. My dad was (what we called back then) a redneck. An Arkansas-born truck driver (all the stereotypes you can think of actually picture him pretty well) who ended up with an only son who was a brainiac. I bet it wasn't easy for him; I know it wasn't easy for me.

A Suprise Move

I look back with more empathy for and understanding of his challenges with our relationship than I had at the time. Here’s an example and something that still surprises me: my dad played chess.

Well, at least at some point, he decided to try. One day, he bought me a chess set and spent time with me. I'm confident he discovered the rules from the brief sheet included in the box and taught me as he taught himself. I think we played on a pretty regular basis for a while.

At the time, I assumed he was interested in the game. Looking back now, I see he was interested in me. I think he was grasping for ways to connect with his alien son. He must have heard that smart people played chess and thought he'd see if it would help us.

I promise you it did.


King's Counsel

What's my point? For much of my life, I didn't think my dad had much to teach me - certainly not with respect to money and finances. I mean, the modest entry-level salary of my first full-time job after college was higher than he had ever earned in his life. He constantly struggled to pay his bills. Many car batteries and tires came from Sears because that was where he had a credit card. When he passed away, my inheritance consisted of a 25-year-old pick-up, a beat-up toolbox, a La-Z-Boy, and a 32" television – sounds like the makings of a country-western song to me!

My perspective has changed. Certainly, there are financial lessons I learned from my father, most notably: "Don't do it that way!" But there are positive takeaways, also. Such as:

“If you want something,
work for it.”

“Take care of what you have.”

“If you're employed by somebody, give them a full day's effort.”


People who know me and knew my dad will tell you there are many, many ways in which we're different. But I'm still my father's son, and I still play chess.


As you celebrate Father's Day this month, consider looking back and asking, "What financial or life lessons - positive or negative - can I take away from my father?" You may be surprised!