Zen and the Art of Real Estate Investing with Jonathan Greene

What Tennis Taught Me About Life


Photo by Martin Sanchez on Unsplash

Photo by Martin Sanchez on Unsplash

My dad taught me how to play tennis at a very young age. It was really the first sport that I ever played consistently. Him and I used to play a lot. When I think of him, I think of him in white tennis shorts and a polo shirt sometimes. Because that was his summer tennis outfit.

I thought I was a really good tennis player growing up. I used to look up the rankings in Tennis magazine all the time, waiting for my day to get there. And just like with many kids, and many sports, my head was in the clouds. I was good. But I literally never practiced. So I wasn’t going to beat kids who had coaches and trainers.

I remember playing my first USTA tournament at 14. I was thinking how cool it would be to win a USTA tournament. I won plenty of hardware (trophies) at camp, but that was like rookie stuff. I thought it was more. It wasn’t.

I played this kid named Chris Reilly. He looked nerdy. As if I didn’t. In the clouds again I was. I came to net on the third point and he lasered one right at me. I fell to avoid it. It was embarrassing. As was the 6–0, 6–1 result. My stepdad took a picture after I got destroyed. Thanks.

I never played another USTA tournament. But I kept playing tennis. I played all through high school. I want to start playing again. Because I love it so much. I love watching it. I love the artistry of shot making. I love the history of the game.

But I also learned a lot about life from tennis. And it’s deeper than you think.


When your backhand sucks or you like to be lazy, slice becomes your friend. It keeps the ball low and can create a skidding effect making it difficult for your opponent to pick it up, especially after a rally of heavy hitting. When you slice, you take the power off and hit the ball lighter. It comes with less risk than heavy topspin or trying to hit a winner down the line.

In life we slice all the time. Those that don’t slice in life are always hitting everything too hard. Always trying to win every single point. Every single project. Every single relationship. But they need slice.

They need to slow down the pace and be more careful with their aim. Because sometimes their opponent will catch on and realize that they don’t know how to slow down. And they will use it against them.

Slice is taking the pressure off. Acknowledging that this particular shot doesn’t have to be perfect. That you don’t have to win right now. Or even look good. It can go slower. And sometimes the slice in a rally is just what is needed to make the opponent (or your partner) react.

Photo by Lucas Davies on Unsplash

Photo by Lucas Davies on Unsplash


Your forehand is your main power source. Your go-to. But the thing is, everyone knows it’s your best. And everyone else has a good forehand too. So it doesn’t make you special.

Your forehand is what is expected. And if it’s not good, you are really in trouble. If your most expected asset is sub-par you can’t make up for that with a really good slice. Because your forehand will be hit to more than anything else.

Your forehand in life is your obvious skill for your job. If you work in law, you should be a good negotiator. If not, you won’t do well. If you work in sales, you better be a people person. If not, you won’t do well.

Without a good forehand, none of the other shots matter. Because you will never achieve what you are seeking without mastering the basic first.


Your backhand is usually your off-hand, in a way. It’s not as good as your forehand. But if you have a really good backhand, you will be a much better player than someone who doesn’t. More well rounded.

It shows you are able to be effective no matter what is thrown at you. If you have to pivot one way, you are fine. If you have to pivot the other, you will be equally adept at taking on that challenge.

Growing up, often our backhand is weak. Because we spend all our time on our forehand. Then on our serve. Then on our volley. Because the backhand is annoying when you are young. And you have to cross your body and basically swing backwards.

But you can’t run around it your whole life. Eventually you grow up and you need your backhand. The competition is fiercer and to be in the discussion you can’t just be one shot, one note. Your backhand is what rounds out your ground game and keeps you even, no matter what comes.

Photo by mitsal dian on Unsplash

Photo by mitsal dian on Unsplash

Drop Shot

A cousin of slice, the drop shot is a surprise tactic. An unexpected play tossed in the ring to take advantage of who is across from you. To make them work harder. To make them strain. To make them prove themselves. To do something unexpected.

A drop shot shows others you aren’t scared to take a little risk for a bigger reward. A drop shot needs to be much closer to perfect than all of your other shots. Because if it’s not a good drop shot, your opponent will get there in time and easily win the point. Because you just set it up for them perfectly.

Your life drop shot is your skill that you don’t publicize all the time. It’s not your main job or life skill. It’s not what people know you for. But you have it. Hidden away for use when necessary.

And when you use it, the surprise alone is part of the effort. And the reaction. Because it wasn’t expected. If done correctly it immediately shifts the balance to you. And now someone else has to hustle to make it work on their end.

You can’t use your drop shot all the time. Because if you do, it will become too commonplace. And the mystery will be gone. Without surprise the drop shot is barren. It’s anticipated. And it won’t work.


Topspin is that extra bit of oomph that you need to make your forehand or backhand really rip. You see a lot of people hitting their strokes flat and hard, but they can be returned easier than when hit with proper topspin.

Topspin requires more effort, more skill and more accuracy. But it produces a higher probability of winning the point. Through practice topspin is what keeps your ball down and then lets it rise back up again to take on your opponent for you.

Your topspin in life is what you are willing to do to learn more about something. You could go along and stay flat, but if you take a better approach, your results could grow exponentially. And so you grow and adapt to a better way.

And suddenly what used to feel contrived and like everyone else, carries a new power to it. It and you are more dynamic because of it. And it makes you more confident in your game.


The serve is what starts every single point in tennis. Without a good serve, you will always be starting behind. And worried. Worried that your opponent is walking up on you to take advantage of your obvious weakness.

A strong serve announces your presence with authority and immediately puts your opponent on their back foot as they try to combat your speed and accuracy with their return. A return which, at times, cannot even be used. Because your serve became an ace.

Your serve is your presentation. Your delivery. Sometimes your elevator pitch. It’s how you approach people. It’s how you win over clients. It’s how you impress your friends.

Your serve is your way in. And when done with speed, power and accuracy it is almost unstoppable. Because you have worked on it so much. You know who you are. So, to you, your serve is just you. Starting a conversation.

But to others who aren’t as suave or haven’t practiced as much, their serve is what will always hold them back. A great idea can be lost by a terrible pitch. Just like a great match can be lost by a double fault.


The volley game is all about touch and angles. Dexterity. Quick reactions. And placement. It’s a way to shrink the court and use a set up shot as an advantage to approach. But the volley does come with risks.

Your opponent can pass you or lob a ball over your head. Or you could blunder as the touch differential between volleying and baseline rallying is stark, especially in the middle of hard fought point.

Some things in life require a little more of an angle. An upgrade in precision to be effective. Think of it as approaching in a riskier way, but with a much bigger potential reward. You come in strong and either way, the issue will come to a resolution sooner than if you just kept hitting the same shots back and forth to each other.

Volleying is about touch. A soft touch. And life can be as well. There are times when we have to be tough, act tough and create a wall to keep ourselves safe. But there are other times when life requires a gentle reminder to go a little easier.

Tennis | Life

Tennis is more like life than most of us think. Many sports are. The correlations are hidden by competition and gamesmanship, but when boiled down to the core, you can see it.

“Tennis is mostly mental. Of course, you must have a lot of physical skill, but you can’t play tennis well and not be a good thinker. You win or lose the match before you even go out there.” — Venus Williams

Our physical attributes can only get us so far. In sports. In dating. In life. We succeed in the long run with our mind. And how we treat other people. Even in competition.

If you’ve watched tennis long enough, you know that every tennis player puts up their hand to acknowledge a lucky shot on their part. One that shouldn’t go in, but does. And they put up their hand as a show of sportsmanship. Because they didn’t mean to do it. And probably didn’t deserve the point.

But they get it. The point. But in this way, tennis players get it. We can plan, work hard, study and train, but sometimes our perfectly lined up winner goes off the side of our racket. And over the fence. And sometimes it still goes in.

“Writing free verse is like playing tennis with the net down.” — Robert Frost

We should all feel like we are playing with the net down.

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