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How To Say Yes To Risk-Taking

Create a present to be proud of in the past.

Photo by Ian Schneider on Unsplash
Photo by Ian Schneider on Unsplash

Recently, I found myself reading the Failure Report. This is the name of a study from Startup Canada and the TruShield Insurance Entrepreneur Success Advisory Council that uncovered how Canadian entrepreneurs view failure.


As a U.S. based entrepreneur, I was curious to see how Canada views small business failure. The statistics are not terribly far off from what we see in the United States. The Failure Report outlined common entrepreneurial failures in Canada which include a lack of financial literacy, market fit, lack of management, and knowledge gaps. Meanwhile, in January 2019 SCORE Mentors shared leading causes of small business failure in the United States. Incompetence ranked the highest at 46%, with lack of managerial experience following closely behind at 30%.

Failure rates aside, one of my favorite parts of the Failure Report is that entrepreneurs surveyed don’t share a common definition of failure. The possibility of failure doesn’t not stop them from taking risks. If anything, it empowers entrepreneurs. 84% surveyed stated that they’re “very likely” to take a risk even if there’s a chance all does not go as planned.

It takes guts to close your eyes and make the leap forward. I cheer on anyone that consistently gets back on the horse after falling off multiple times. Fortune may favor the bold, but it’s not always easy to talk yourself into taking yet another risk. Here’s what entrepreneurs can do now to ensure they remain open and ready to actively take risks.

Give yourself pep talks peppered with positive phrases

The Failure Report revealed that when entrepreneurs are likely to use positive words when they describe what failure means to them. Some of these words include “opportunity” and “chance” along with phrases like “try again” and “do better.”

As an entrepreneur, give yourself a pep talk loaded with positive words and phrases. Ditch expressions like “this is your last shot” or “I’m quitting if this doesn’t work out.” These serve as self-imposed ultimatums that do less to empower you than you think. If you set yourself up with the implication that you might fail from the start, there’s not much to motivate you to cross the finish line.

Remember risk taking leads to the unknown

There’s a wonderful quote that encourages people to go out on a limb because that’s where the fruit is. You can’t know what kind of fruit it is until you try and go out on a limb for it.

This quote sums up the experience of life, which is a series of great unknowns. Timing and willingness to say “yes” often charts the course for our lives and the lives of others. We can’t know for sure what will happen next, but we do know that nothing happens if there isn’t effort. If you ever feel like the risk isn’t worth the reward, think about that fruit-filled tree. It’s always there with new and surprising opportunities clustered on it. All you have to do is be brave enough to reach out and grab on.

Create a present to be proud of in the past

Huh? Let me break this down. One day, you will look back on what is right now your present place in the world. Most of us spend the present thinking about the future and trying to learn from mistakes made in the past. Eventually, the present will become the past and turn into a time you look back on.

How will you feel when you reflect on your then-present? Did you make the most of opportunities presented to you or try new things? Even if things were tough, did you push on and remain determined not to give up? Or, did you let fear of risk get the best of you?

Hopefully, you feel satisfied that you gave it your all in the once-present. If not, there’s still time. You can create a present that you can reflect back on with pride. All it takes is the ability to close your eyes and make the leap forward.

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