Hey everyone, I wanted to take a moment to share a recent decision I had to make that led me to reflect deeply on the idea of playing to win versus playing not to lose. You see, these two mindsets can make all the difference in the trajectory of our lives. Let me walk you through this decision and how it’s changed my perspective.

So, here’s the deal. One of my businesses was hit hard due to a shutdown, affecting my cash flow. As a website designer, I rely heavily on a software tool that’s been a game-changer for me. When I first got started, this software was a steal at $99, giving me the freedom to design unlimited websites. But over the years, the limits tightened, and my renewal cost went up to $200.

Now, I currently use this software for 25 websites. The new pricing model would have meant shelling out $200 just to maintain those 25 sites. But here’s the kicker: if I didn’t renew and decided to update later, it would have cost me $200 for only 25 sites. The new pricing was a whopping $350 for a thousand websites.

It was decision time, and I found myself at a crossroads. I didn’t have $200 lying around, and I was already stretching to cover my mortgage. Yet, I knew that if I didn’t update and my websites crashed, it would be even costlier down the line. So, I had to make a choice—play it safe or take a calculated risk.

This is where the concept of playing to win versus playing not to lose came to mind. I’d heard about this from Dan Peña, a figure known for his straightforward approach. Some might not like his style, but I believe in listening to the message rather than focusing on the messenger.

As I reflected on my situation, I realized that many times in my life, I’ve opted for the safe route. I’d chosen to avoid potential losses rather than aiming for significant gains. And it hit me: I needed to shift my mindset.

A few years back, I took a UX/UI design course. While my classmates hesitated to spend $9 on web hosting, I was already investing $50 a month. Why? Because I understood that investing in learning and growth was essential. I wasn’t playing not to lose; I was playing to win. I knew that the knowledge and skills I gained would pay off down the road.

I also realized the delicate balance between playing to win and making impulsive decisions driven by vanity. There’s a difference between upgrading tools for real growth and making purchases that don’t align with our goals. It’s about mastering the basics before jumping into advanced territories.

Let me share a personal story that brings this home. I’m a martial arts school owner, and I’ve struggled to find the right balance between playing it safe and playing to win. In the early days, I focused on perfecting my teaching skills but didn’t pay enough attention to the business side. My rent was cheap, but my profit was minimal.

Then came a pivotal moment when my building was sold, and I moved to a bigger space. My rent doubled, but my profits tripled. It hit me that by playing not to lose, I was holding myself back from achieving my full potential. I needed to play to win and aim for higher levels of success.

Fast forward to today, and I’m facing another crossroads. My goal is to open a martial arts school in a larger city, where the demographic is more promising. Yes, the rent will be higher, but the potential for growth is immense. This is where the paradigm shift comes in—playing to win by taking calculated risks, even if it means stepping out of my comfort zone.

So, I urge you to consider this concept the next time you’re faced with an important decision. Ask yourself, am I playing it safe or am I aiming to win? It’s not about reckless spending but about recognizing opportunities that have the potential to transform your life. It’s about understanding that sometimes, the most significant gains lie just beyond the edge of your comfort zone.

Thanks for joining me on this journey of self-discovery. If this resonates with you, I’d love to hear your thoughts in the comments below. And if you’re ready to shift your perspective, don’t forget to hit that subscribe button. Until next time, keep playing to win.

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