The Fraidy Cat Entrepreneur by @jennieormson

The Fraidy Cat Entrepreneur

by Jennie Ormson | Featured Contributor 

Did you hear about that entrepreneur that couldn’t get past her fear? Ya, neither did I. Because she no longer exists. Fear had her pinned in a chokehold up against the wall and she didn’t fight back. Her dreams died. Her plans fizzled. The energy drained out of her big ideas and she slunk back to the 9-5 utterly defeated and shaken. She left fear behind and wrapped herself in the cocoon of someone else’s corporation, someone else’s dreams, risks, and decision-making.

Being an entrepreneur entails pushing our relationship with ourselves to the very limits and back. Owning your own business will strain you and stretch you and kick up every fear you’ve ever imagined, and many you haven’t.

          Will they like me?

          Will they like my product/service/program?

          Will it float or will it flop?

          What if …?

                    What if…?

                              What if… ?

If I was the sweet, soft, squishy type I’d stroke your head and say “Shhh, shhh, shhh, there there now. Fear is a liar.”. Fortunately I’m not the sweet, soft, squishy type. I’m a realist who’s here to help entrepreneurs grow and push through their limits. Sure, sometimes fear is a liar. Sometimes the thing we stress and struggle over never comes to pass and we’ve wasted a whack load of sleep, energy, and time over nothing.

But sometimes fear IS NOT a liar. Sometimes the things we fear DO come to pass. When we give in to our fear we drop the ideas or drop the ball. Fear can freeze us and convince us that taking that risk is a bad idea. IF we listen to it.

I’ve been circulating in the world of high achievers for close to two decades now, learning what makes them tick and fires them up. I have yet to hear from a successful business owner:

“Every single thing I tried was a massive success. Failure? I can’t think of any.”

One of my favourite topics to discuss with entrepreneurs is the efforts that didn’t work. The bombs. The Bad Ideas. The poorly executed pitches. The flops. The really funny part is that usually they begin their response with a laugh or smile as they go on to recall and recount their tale. But these aren’t tales of woe. These are tales of learning. They didn’t let the failures break them. They learn from it and carry on.

As an adult, after not skating for a decade, I decided to take skating lessons. We were all a bit wobbly on the ice those first few minutes, sticking to the safe strokes and easy glides. On that very first day the instructors did something brilliant: they made us fall. Intentionally. Over and over again. They also taught us how to get back up safely without our feet flying out from under us. This allowed us to try bigger and bolder moves: skating faster, skating backwards, cross overs, crosscuts, turns, and stops. Was I scared? Hell ya. Did I do it anyway? Absolutely.

Now every winter I make the trip to the Rideau Canal in Ottawa, skating for miles on the world’s longest outdoor skating rink with confidence and delight. It was about more than skating. It was about wanting to do something well. Learning something new (or relearning it). Facing the fear. Putting in the hours, risking embarrassment and judgment, and ploughing on ahead. As entrepreneurs, stubbornness is an asset that will offset fear. Learning to fall, on the ice and in business, is absolutely necessary if we want to be successful.

Feel the fear and do it anyway.

Will there be judgment and rejection from some people? Most certainly. Will you survive? Most definitely. You won’t appeal to everyone and that’s just fine. Will some endeavors sink like a stone? Yup. Will you be alright? Sure. Just because some ventures fail, it doesn’t mean YOU are a failure. Don’t catastrophize the losses – learn from them. Sift through the ashes and rubble to figure out what you could have done differently, done better. Pick yourself up, dust yourself off, and get back out there. Remember why you started.


Jennie OrmsonJennie Ormson knows the power of a strong relationship, and the impact of a crummy partnership. As a Relationship Expert, her mission is to empower people with the skills they need to communicate effectively, fight fair, and revive the sparkle. Jennie’s core belief is that there is immense power in being heard and feeling understood. Her gift is helping couples understand what’s going on in their emotional landscape, and how to navigate the peaks and valleys. She’s relatable and practical, helping people to balance speaking up and knowing when to shut up.

For over 20 years as a therapist, Jennie has provided insight, compassion, and the ability to thrive. Her work in Canada, America, Ireland, and the UK has impacted thousands of lives. With three young kids, a booming private practice, an exciting online venture, and a partner of 25 years, Jennie understands the need to juggle it all with grace and humour.

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