Are You Still Cocky?

By Randy H. Nelson

Entrepreneurs are described many different ways. Ambitious, driven, creative, and passionate, to name a few. One of the less complimentary descriptions that I hear quite often is that entrepreneurs are “cocky” individuals. In my experience, it is a fair characterization. No doubt that I was cocky earlier in my entrepreneurial life. What does that mean?

Cocky: overly self-confident, arrogant, and conceited

When I read the definition above, it is not hard to see why I had that attitude. I certainly was overly self-confident that our startup was going to work, and once the business took off like a rocket, my arrogance grew as well.

Arrogant: having an exaggerated sense of one’s own importance or abilities

I don’t believe these are bad traits for entrepreneurs to have—in the beginning. As entrepreneurs, we are well-known to the outside world as risk-takers, and we start businesses to gain autonomy. In addition to our willingness to work extremely long hours, being cocky is most likely one of the critical personality traits that leads to our early-stage growth and success. In the beginning, I was most assuredly over self-confident of my own abilities, leading our startups with my partners with a “glass is 99.5% full” mentality.

Warren Buffet has been quoted as saying, “You only find out who is swimming naked when the tide goes out.” One of my favorite phrases is, “Trees don’t grow to the skies.” To me, these two quotes share a similar message: Nothing lasts forever, especially unmitigated success.

We will all experience ups and downs, and successes and failures in our lifetime. Eventually, business and life humble you. This is when the learning begins.

Humble: modest estimate of one’s importance

Throughout their careers, great entrepreneurs and leaders come to the realization that it is not all about them, but rather, it takes a great team around them to become successful. I firmly believe—just like the evolution of children into productive adults—cocky entrepreneurs should evolve over time into more humble entrepreneurs and leaders.

My challenge for you is to continue to evolve. In my Decision Series books for entrepreneurs and leaders, I challenge everyone to grow their self-awareness and their leadership skills, as a lack of self-awareness is the fatal flaw of a leader, and the growth of a company is limited by the growth of its leaders.

What does the next best version of you look like? Are you still just cocky?


Randy H. Nelson is a serial entrepreneur, speaker, coach, former nuclear submarine officer, and author of The Second Decision with ForbesBooks. Learn more at randyhnelson.com.

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