When Playing Becomes Winning

Almost exactly a year ago, I discovered pickleball at a Sabah Computer Society family outing. Having played badminton for decades, I enjoy the pace and agility required on the court. Pickleball feels much slower and I thought it might be too boring for me. I couldn't have been more wrong.

After a few sessions, I was hooked. Since then, I've been playing every week alongside badminton. There are some transferable skills like split steps and overhead shots but I also had to learn different grips and shots that are unique to pickleball which makes it fun and enjoyable.

Every time I learn a new shot, I try to repeat it often in casual sessions, sometimes to the detriment of winning the game. The process of figuring out the paddle angle, swing path and body mechanics can be quite intriguing. And it's very satisfying when I manage to execute it, even if inconsistently.

From Playing to Winning

Thankfully, after grinding at it for months and making lots of mistakes, my skills improved enough to give me a chance of winning some games. That fueled my desire to get better, because no one can deny the sweet taste of victory, even if it only comes occasionally.

Like in many sports, the path to winning is not just about outplaying your opponents, but also about limiting your own mistakes. I wrote about unforced errors before, mistakes that are avoidable and completely within your control. Every miss is a point for your opponent and one less for you, so you start to fuss over every shot you make.

When the Game Became Serious Business

I started to learn about shot selection and court positioning. I watched videos to improve my forehand drive and researched which paddle would better fit my playing style. At times, I even felt the urge to "advise" my doubles partner on how they should play.

Games went from being a fun workout to a full-blown analysis on what I could have done better. Maybe I should have taken the shot, or maybe my partner should have hit a different one. Then it all unravels when I deliver the losing shot and let my partner down, especially against opponents I feel we shouldn't be losing to.

All the fun and joy of learning how to execute a shot and having fun with friends became overshadowed by the frustration of missing the sweet spot and losing games I felt we should have won. I started to wonder, when did playing pickleball become less about playing and more about winning?

The Beginner Mindset

In early-stage startups, everyone in the company is focused on building the product and finding product-market fit. The team explores every opportunity, tests every idea and learns from every mistake to build a sustainable business. Nothing is too sacred to question and you celebrate every win, no matter how small.

This phase is similar to when you first discover a new sport or hobby. You are intoxicated by the possibilities and vast potential of your new pursuit. Never mind that you probably aren't any good at it yet nor have the necessary skills. You are willing to commit to the path to see where it goes.

When the Scoreboard Appears

Hopefully, after all the sleepless nights and sacrifices from the team, the product gains traction and the business starts to grow. The focus moves from building what customers want to scaling the company and team to deliver more and gain market share.

Conversations in the leadership team shift from debating about which feature to build to which markets to enter. You start obsessing over growth metrics and competitors' moves. Suddenly there's a scoreboard and you intend to be at the top of it.

Beyond the Scoreboard

In sports like pickleball, the score tells me whether I'm winning the game. In business, revenue and growth metrics tell me whether we're winning the market.

But numbers only tell part of the story. I've written before about how targets, forecasts and projections can help us understand where a business is heading, but they don't tell us everything about the business itself.

The same is true here. The scoreboard tells me whether I'm winning, but it doesn't tell me whether I'm still enjoying the game.

Don't get me wrong, keeping score is important and winning is part of what makes it fun. But if the drive to win takes away the fun of playing the game, how long can you keep playing at your best?

Remember Why You Play

You can't remove the element of competition from sports and business. Winning is part of how we keep score, but the journey and effort that goes into getting there matter just as much. Sometimes we can be very successful at producing the outcome we're chasing and still wonder whether the time spent getting there was well spent.

Would you rather have a fun and enjoyable ride or a miserable and torturous journey down the road of success?

I think you can choose to play and enjoy the game without making it all about winning. You can also adopt a winning mindset without forgetting the joy that made you want to play the game in the first place.

It's definitely easier to focus of the joy of the game when you are a beginner. I started playing tennis, and it's refreshing to be able to focus on improving my shots without any expectations of winning. But even then, as I get better, I know competitive instinct will creep in and I'll start wanting to win more.

When that happens, I'll need to remind myself the reason I started playing in the first place.