win more by caring less

Feeding an Obsession to Win

As a teenager, I used to love playing tennis. Most of my time would be spent hitting a ball against a brick wall because tennis lessons were so expensive. But I was obsessed with improving my game so I could win.

I was dedicated. I put the work in. A winning formula, right?


How to Work Against Yourself

Picture a crucial match point, the tension mounting, and….my well-honed technique crumbling under the weight of my obsession with victory.

When the game was on the line – when it mattered the most – all of that excellent technique cultivated by hours spent practising went to pieces.

Why did this happen?

I was too attached to the outcome. It wasn’t just about wining a game, it was about the status that came with it and a story I told myself about winning and losing. This pattern played out in other areas of my life too:

* in chasing good academic grades.
* in chasing outward indicators of success.
* in chasing the approval of others.

The more I chased, the faster the finish line ran away from me.

My intense desire to win started to undermine all of the effort I had put in.

Winning More by Caring Less

Through loss after frustrating loss on the tennis court, I learned to loosen my grip on the outcome a little bit at a time.

Fast forward to today; I approach tennis with a free swinging freedom because I have been released from most of my teenage fixation on the win.

To clarify, I still love to win. But now I embrace the win of every ball I hit cleanly. The points or the match victories that may come with it are a bonus.

As a result, I actually win more often when I care less about the result.

With this teenage tennis turmoil dissolving, this counterproductive pattern disappeared from other areas of my life too.

For an example of this pattern manifesting as chasing the approval of others, I published a story on my quest to acquire a 1970s Corvette Stingray because I wanted to appear cool (with embarassing results). For more, see last week’s story: Are You Chasing Status Symbols or Soul Desires?

Carefree Creativity

The concept of caring less for winning more can be applied to your creativity as well. How often have you found yourself stuck, staring at a blank page, when you try to force an outcome?

The pressure to meet certain expectations can lead to that dreaded writer’s block[1] or creative stagnation.

Let Go of Winning, Embrace Magic

However, when you release your tight grip on the end result and allow yourself to flow freely, something magical happens.

Much like the graceful, instinctive movements in your favourite physical activities – whether it be sport, dancing or walking a nature trail – creativity flows effortlessly when you’re unburdened by expectations.

The Takeaway

🔨Whether you’re crafting a presentation, brainstorming ideas, or painting a canvas, try loosening the reins of perfectionism.
🔨 Embrace the process, find joy in the journey, and watch as the results unfold naturally with consistent effort.


[1] If writer’s block is a problem for you, this quick read might help: Why Your Ideas Feel Like They Are Trapped In A Secret Chamber of Your Mind

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