Calculated Risks, Failure & Triumph with Dorothy Enriquez

The most successful people understand the power of failure and calculated risks. To most individuals, failures seem like a punishment or a mishap that should not have happened in the first place. The truth is success comes with a certain degree of failure and taking calculated risks. Research shows that triumphant, humble leaders took calculated risks and experienced failure numerous times.

What most people don’t realize is that challenges give rise to a golden learning experience that helps you grow. Failures give one valuable real-life lesson that fosters them to be better. On the other hand, risks should be a feature every entrepreneur or anyone looking to succeed has. Risks allow people to experiment and see what different sides hold for them. The best experiences exist on the unspoken side. It’s upon you to spread your wings and see what that side holds. Again it’s advisable to take calculated risks.

Risks can be risky, and because you want to excel so bad doesn’t mean you have to make aimless actions. It would be best to analyze the situations first and see the possibility of winning and the loss you will make if things go wrong. It should be something you can handle if the result comes out either way. 

It’s worth noting that failure fosters humility and great leaders. Again your chance of success is almost inevitable after failing a certain amount of times and after several calculated risks. For those afraid of taking risks or wondering whether it is worth it or whether it will work out for them, you ought to look at Dorothy Enriquez’s story to make your judgment.

The article consists of answers from an interview with Dorothy Enriquez on each section in this article to ensure you have the highest possible chance of success. 

Dorothy is a leadership development expert and understands failure all too well. For many, the pandemic hit hard, but as someone like her who evolves constantly, she not only survived but made more money than ever in business. She was a rising star Nominee in 2020 in the Wisconsin MarketPlace Awards, the 2021 Rising Star Award winner in the Minority Business Enterprise category, and has written for Forbes and Training Industry Magazine.

She has something to teach us regarding calculated risks, failure, and triumph.

Calculated Risks

Dorothy has taken many calculated risks that have made her achieve great strides. 

As a leader and as a business owner, you’re going to have to take calculated risks even in life. But did you know that even playing safe has a record of risk? Sounds ironic, right? Yes, if you are playing it safe, it risks your future legacy. It attempts what could have been if you dared yourself to be great. 

Understanding that it’s natural to take those risks should give you peace of mind. 

Most people only see what they believe and nothing beyond that, so it’s always important as a leader to get help from other people you see as mentors or people who have done what you want in your space. 


Everyone that has ever lived has gone through failure. However, the people who succeed view failure differently than those who don’t. People who see failure with negative connotations stop their behavior and do not try anymore. 

Life circumstances forced Dorothy to quit her job, and six months later, she was broke and broken. Having not more than $75 to her name and dim hopes of getting back up, she got her father’s psychological support. She was able to get herself a job as a contractor for six months, and over the years, things began to fall in place.

Successful people, however, see failure as one step closer to success. To them, failure is just one way that didn’t work. It doesn’t mean that the destination came to a halt. Instead, they see themselves trying again in a new way.

Let’s say you’re only 50 tries from getting it right. How much quicker would you want to go through those 50 tries? How much faster would you like to fail?

Making the Decision 

Triumph isn’t a destination. It’s a decision. It comes from when you say enough is enough, and you make the change.

In this article, you’ve learned that failing is a natural part of life. It’s a necessity if you want to become triumphant. 

When people say the journey is what matters, they’re saying that you’ll never get to the endpoint until you pass on to the next life.

When you decide to win, you take a stand every day with the decision to choose to be powerful, to choose to be successful, to choose to be the best version of yourself.

By becoming decisive, you’ll notice you commit to decisions instead of continually second-guessing. You would get to a point where you don’t have to ask seven people what they think to help you decide.