Swinging Big - Why Simplicity Is Important in Pickleball and Investing

I enjoy pickleball. So while visiting Hilton Head recently, I showed up for open play, expecting a casual mix of games and players.

I stepped onto the court with a few younger players—and one gentleman who had to be close to 80 years old. Naturally, the thought crossed my mind: Do I need to take it easy?

That question didn’t last long.

Within the first few points, it was clear—this guy wasn’t just keeping up. He was dominating the game. Always in the right spot. Calm. Patient. Every shot had a purpose.

At one point, I floated a ball a little too high. He slammed it past us and laughed:

“That’s a ham sandwich, and I like those.”

Later, after one of my shots sat up just long enough, he joked again:

“That one was a ham sandwich with cheese.”

I thought, “Not only are we getting taken to school by this 80-year-old, but we are getting trash talked too??”

For two straight hours, he never lost and never left the top court.

After we finished, I talked with him and learned he was a former state champion tennis player. That explained the skill—and watching him play taught me something more.

What stood out wasn’t just what he did on the court. It was what he didn’t do.

No flashy shots.

No unnecessary risks.

No trying to do too much.

He kept it simple. He stayed consistent. He let the other team make mistakes—and they did.

We see the same dynamic all the time in investing.

There’s a temptation to swing big. To chase the next hot idea. To believe that better results come from more action, more complexity, more “doing.”

But often, the best outcomes come from discipline and restraint.

Some of the best decisions our clients point to aren’t the investments made — they’re the ones avoided.

• The speculative investment that didn’t fit the plan.
• The private deal that sounded compelling – but didn’t make sense for their goals.
• The emotional move we avoided during market volatility.
• The urge to react when patience was the better play.

Just like that pickleball match, success isn’t about hitting the hardest shot on the court. It’s about positioning, consistency, and knowing when not to swing.

That 80-year-old didn’t dominate because he took big risks.

He dominated because he didn’t.

At Rather & Kittrell, that’s how we approach financial planning. Not complicated for the sake of complexity. Just thoughtful, intentional decisions over time.

Sometimes the smartest move isn’t the one that looks impressive in the moment—it’s the one that keeps you in the game.

If you’re wondering whether your current strategy is helping you stay disciplined—or tempting you to swing too hard—we’re always happy to have a conversation. A second set of eyes can make all the difference.

Sam Paganelli, CFA® CFP® is an Advisor with Rather & Kittrell.