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Investing Lessons From Pickleball

They both take time and practice


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I’ve been in finance for the last four decades, and think I know a fair amount about investing. But I’m relatively new to the fast-growing sport of pickleball. Many things I’m learning about playing pickleball are applicable to investing as well. Here’s some of what I’ve learned that perhaps you can use in your investing.

1. Pickleball is about not losing

Great as it feels when I hit a winning shot, I tend to lose the match. Pickleball is a game of percentages, and it’s the player or team who makes the fewest mistakes that wins the day. This is also what investing is about. Sure, I can go for a winner and try to find the next Nvidia (up 239 percent in 2023), but the odds are low I’ll succeed and much greater that I’ll buy poorly performing companies.

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The better strategy is to own every company in a low-cost total stock index fund, because owning every company at the lowest costs guarantees I’ll beat most investors in the long run. I like those odds, and with this strategy I end up beating the vast majority of professionals. Even those who beat me over a year or two are unlikely to consistently beat me. In fact, my total stock index fund has even bested Warren Buffett’s Berkshire Hathaway over the past 15 years. That’s kind of like beating Ben Johns, the world’s number one ranked pickleball player.

2. My pickleball instincts are wrong

Having been a tennis player for many years, I’ve learned my instincts for that game don’t transfer well to pickleball; they are, in fact, completely wrong. If I have a fairly easy shot, my tennis instincts tell me to hit it hard. Time after time I’ve watched what I thought was a great hard shot I hit that ends up easily coming back to me, softly hit and perfectly placed to make it somewhere between hard and impossible for me to return. My instincts are wrong, just like in investing.

When markets plunge, our instinct is to run for the hills and sell. Then, when stocks hit an all-time high, we instinctively think it’s safe to return to the stock market. Though the logic is clear that doing the opposite — buying low and selling high — is superior, we have to overcome our instincts. It’s a really hard thing to do. In fact, I tell people if a financial move feels good, it’s probably the wrong thing to do. If it feels all wrong; that’s a good sign.

Video: Get Ready for the Pickleball Court With These Stretches

3. I keep repeating the same pickleball mistakes

I know the theory behind many pickleball shots, and the logic makes perfect sense. I know how important footwork is, as is being stationary when hitting the ball. Yet despite knowing what I should be doing, I keep making the same mistakes over and over again. It takes a lot of practice and muscle memory to reach consistency, or so I’m told.

When it comes to investing, I see people repeating the same mistakes over and over again. Often times, they will say something like “this time is different,” or discuss some knowledge they’ve recently acquired from TV or a financial publication, as if they were the only ones who had this knowledge and it wasn’t already priced into the market.

4. Pickleball is very social

I have met some of the nicest people playing pickleball. They are interesting, encouraging and always willing to give me pointers to improve my game. Even those people I play who are much better than me encourage me to keep playing with them.

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In investing, there is a group known as the Bogleheads (named after the late Vanguard founder, John C. Bogle) who are also some of the nicest people I’ve had the pleasure to meet. They too are interesting, encouraging and always willing to help others become better investors, without any personal gain. You can find answers to most financial planning questions on their forum Bogleheads.org. If the answer isn’t there, you can post your question and are likely to get answers from people who aren’t trying to sell you anything. One of the two founders of the Bogleheads movement is Taylor Larimore, who just celebrated his 100th birthday and is still helping others.

5. Pickleball is inexpensive

Unlike golf, with its expensive green fees and cart rentals, pickleball court time is often free and the equipment fairly inexpensive. Also, unlike tennis, you don’t have to open a new can of balls every day.  Pickleballs are plastic.

Investing must be inexpensive as well. Expensive funds are very unlikely to outperform the lowest cost index funds, which typically charge somewhere between nothing to about 0.07% annually. That means that for each $10,000 you invest, you’ll pay between nothing and $7 a year. John Bogle would often say about investing that “you get what you don’t pay for.” 

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Video: How to Serve Like a Pro in Pickleball

6. It takes time to improve at pickleball

My expectations were far too high when I started playing pickleball. This is an easy game, I thought. Boy was I wrong. Learning the game has definitely been a two-steps-forward-one-step-back process. There have been some truly horrible outings that made me want to turn in my paddle. But with the support of my pickleball friends who keep encouraging me to come back, I keep coming back.

Investing is similar. Markets can be quite bad for a very long period of time. They can be so bad that many people want to give up and stash their cash under the mattress. Investing is about the long run and perseverance during the bad times. There are never any guarantees. But those that stick with it for long periods of time have been rewarded in the past, and likely will be in the future.

While I think there are so many similarities between pickleball and investing, it certainly isn’t the perfect comparison. Pickleball is actually fun and, many would say, even addicting. And that’s the largest difference when comparing pickleball with investing; investing should be neither fun nor addicting. If you are having fun with investing, you are likely speculating and likely do worse than the market.

The late Nobel Laureate economist Paul Samuelson once said, “Investing should be more like watching paint dry or watching grass grow. If you want excitement, take $800 and go to Las Vegas.”

I say save the $800 and take up pickleball. It’s also better exercise than sitting at the blackjack table.

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