Ep 179: Are You Playing Small?

small, play, entrepreneur

July 10, 2023

When it comes to achieving success, there’s a big difference between playing small and playing to win. This realization hit me in 2016 during a conversation with a mentor. At the time, I believed I had reached the pinnacle of my career. Our business had surpassed the seven-figure mark, and I was mentoring a group of thriving entrepreneurs. However, my mentor saw something I didn’t. He pointed out that I was underperforming my potential and getting too comfortable with our accomplishments. This experience sparked a powerful revelation about the need to aim higher. Are you playing small? Let’s find out! 

Are You Playing Small?

The Comfort Zone and Playing Defense

Often, as entrepreneurs, we fall into the trap of playing small when we achieve a certain level of success. We start to play defense, protecting what we have rather than striving for greater heights. I compared it to a basketball team with a substantial lead at halftime. If their strategy is to defend that lead rather than extend it, the opposing team may seize the opportunity and turn the game around. Similarly, as entrepreneurs, we need to avoid complacency and play to win, continually pushing for growth and innovation.

Expanding Beyond Past Achievements

In that eye-opening moment with my mentor, I realized that resting on past achievements wasn’t enough. Playing to win meant embracing a mindset that extended beyond a specific goal or financial milestone. It involved recognizing the areas in my life where I wasn’t living up to my full potential and challenging myself to grow as a spouse, parent, and leader. True success comes from aligning with our calling and constantly striving to become the best version of ourselves.

The Plague of Playing Small

Playing small is a common affliction among entrepreneurs, often going unnoticed. By understanding and acknowledging the difference between playing small and playing to win, you can gain a significant advantage over others. In the following sections, we’ll explore the concept of boldly moving forward, setting bold goals, and overcoming the barriers that keep us stuck in mediocrity.

Boldly Forward: Pursuing Ultimate Freedom and Prosperity

At our recent retreat, we gathered a group of entrepreneurs called the Incubator members. These individuals spend nine months working together to achieve big goals, foster growth, and create momentum in their businesses. However, the last few months can be challenging as complacency sets in. To combat this, our retreat theme was “Boldly Forward.” It emphasized the importance of looking ahead, embracing risk, and living a life aligned with our calling. Being boldly forward means being a risk-taker, innovator, and visionary leader.

Embrace Being a Little Bit Crazy

Successful entrepreneurs are often seen as a little bit crazy because of the risks they’re willing to take. Others may question their decisions, wondering why they would venture into uncharted territories. However, being boldly forward requires embracing the craziness and venturing beyond the safe and comfortable. It means being willing to fail, learn from failures, and reiterate. The willingness to be a little bit crazy sets apart those who play small from those who play to win.

The Fear of Failure and Taking Risks

Fear of failure is a common reason why many entrepreneurs choose to play it safe and avoid taking risks. The fear of stepping outside their comfort zone and potentially falling short holds them back. However, failure is not the enemy; it’s an opportunity for growth and improvement. We must shift our perspective and view failure as valuable information that guides us toward success. 

Resistance to Change and Embracing Growth

Another reason entrepreneurs play small is their resistance to change. Change can be uncomfortable, challenging, and disruptive to our routines. However, growth only happens when we embrace change and adapt to new circumstances. To play to win, we must recognize the resistance and actively work to overcome it. Embracing growth means constantly evolving, seeking out new knowledge, and challenging ourselves to improve.

From Playing Small to Going for Gold

Playing small limits our potential for personal and professional growth. It keeps us confined to a comfort zone and prevents us from seizing new opportunities. To shift from playing small to going for gold, we must embrace internal competition. This means competing against ourselves, setting audacious goals, and constantly challenging ourselves to surpass our own achievements. It’s about embracing growth and development instead of settling for maintenance and stagnation.

The Dangers of Playing Small

Staying within the realm of playing small hinders us from reaching our true potential. It restricts our growth, limits our impact, and closes doors to new possibilities. By playing to win, we open ourselves up to a world of opportunities and create momentum that propels us forward. Playing to win is about creating a movement, making a lasting impact, and leaving a legacy.

Are You Playing Small?

In entrepreneurship, there is a stark contrast between playing small and playing to win. By embracing boldness, taking risks, and setting audacious goals, entrepreneurs can unlock their full potential and achieve greater success. It requires overcoming the fear of failure, embracing change, and challenging the status quo. Playing small limits our growth and keeps us from seizing new opportunities. It’s time to break free from the limitations of playing small and embrace the rewards of playing to win. Let’s unleash the power of boldness in entrepreneurship and create a legacy that inspires others to do the same.



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