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I work with entrepreneurs and business leaders for a living, and in recruiting members for our groups, I regularly talk with “would-be” entrepreneurs. From an outsider’s perspective, it must look interesting to be an entrepreneur. Some must imagine that being an entrepreneur is full of excitement and freedom. In reality, it can be scary to be an entrepreneur.

I was drawn to become an entrepreneur in the late 1980s after 13 years with IBM. In 1987, I went to work for an independent distributor and, over the next 36 months, watched them build it into a $300 million company and sell it to StorageTek. I knew the guys who started and ran that company. Their background was not much different than mine. I said to myself, “I can do that.” I could not have been more naive. Being an entrepreneur means you have no idea what it’s like to create a company until you do it, as I found out for the first time in 1989. Starting a business can be compared to getting married. But in business, as in marriage, the skills you need to be successful can be learned. As a result, I thought this would be a good time for reflection.

As an entrepreneur, you are no stranger to the world of risk-taking. But how do you conquer the fear that often accompanies these crucial decision-making moments? This article will explore the importance of embracing risk, learning from failure, and cultivating a growth mindset to help you on your journey to fearless entrepreneurship.

Understand the Importance of Risk-Taking:

Risk-taking is an essential component of entrepreneurship. Without risks, there would be no innovation, no growth, and no progress. The most successful entrepreneurs have taken calculated risks to propel their businesses forward. By learning to embrace risk, you open yourself up to new opportunities and, ultimately, success.

Face Your Fears:

To overcome the fear of risk-taking, first, identify your fears. Are you worried about failure, financial loss, or the opinions of others? Once you’ve pinpointed your fears, confront them head-on. Remember that failure is not the end but a learning opportunity, and financial setbacks can be mitigated through careful planning.

Cultivate a Growth Mindset:

A growth mindset is a belief that abilities and intelligence can be developed through hard work and dedication. Embrace the idea that you can learn from your mistakes and grow. This mindset will enable you to view risk-taking as an opportunity for growth, rather than something to be feared.

Learn from Failure:

Failure is a natural part of entrepreneurship. When you face setbacks, take the time to analyze what went wrong, and identify areas for improvement. By viewing failure as a learning experience, you can minimize the fear of risk-taking and set yourself up for future success.

Build a Support Network:

Surround yourself with like-minded individuals who understand and support your entrepreneurial journey. A solid support network will help you gain the confidence to take risks and provide valuable advice when faced with difficult decisions. It is why I created our groups.

Plan and Prepare:

Although risk-taking is essential, it doesn’t mean you should dive in without preparation. Carefully analyze potential risks, develop a solid plan, and create contingencies to mitigate any adverse outcomes. The more prepared you are, the more confident you will feel in taking calculated risks.

Start Small and Scale:

If the idea of taking a significant risk is too daunting, begin with smaller risks and gradually work your way up. As you gain experience and confidence, you’ll become more comfortable taking on larger, more impactful risks that can lead to greater rewards.


Over the last 40 years, I’ve had successes and failures. If I had stayed with IBM, I would have had a more stable life but missed out on many adventures. More importantly, I would have missed many life lessons. Risk-taking is a fundamental aspect of entrepreneurship.

By understanding its importance, confronting your fears, cultivating a growth mindset, learning from failure, building a support network, planning, and starting small, you can overcome the fear of risk-taking and become a more confident, fearless entrepreneur. Embrace the uncertainty and remember that the greatest successes often come from the most significant risks.

After you have completed your journey, I would love to hear about your adventures!