05/07/2014 05:58 EDT | Updated 07/07/2014 05:59 EDT

The Key to Winning Is Simpler Than You Think

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When I won Canada's #1 Female Entrepreneur of the year the second year in a row I proceeded to email the publishers of the magazines who present Canada's #1 Female Entrepreneur Award and threw myself under the bus.

"Ian and Jane -- I think your auto-format document for the award from last year was accidentally re-sent to me. I am sure this year's winner would like to know that she took the big prize, so I thought I ought to pass along the below to show you that the email was re-sent to me again this year."

How is that for not truly considering I would win two years in a row?

I will not share the follow up emails but I will tell you this, they involved some cuss words in embarrassment from me and a lot of laughs on both sides of the forthcoming email threads...and it also included drinking half a bottle of wine while sitting in disbelief.

I could give you the standard list of the top 10 reasons why this or that...the top five ways to grow....the top three times to write down a good idea....and so on. I will save those for future posts on those subjects. You came here to find out specifically how I won two years in a row....and I am prepared to tell you.

Here is the secret to how I won two years in a row: I dared to apply two years in a row.

Sounds like I think I am kind of a big deal, eh?

Well, as it stands I have never thought I was that big of a deal. It is only for the fact that people make a big deal of individuals or businesses which make them a big deal. For all of the rest of the time, that big-deal individual or business (if it is worth its weight) is just simply trying to keep it all together, grow their business or career and hopefully stay humble enough to recognize that every award or grade or accolade is dependent on whomever else applied or did not apply either themselves or for any given award.

In simple terms, every dog has his day in the sun, so long as he is willing to put himself out there, win or lose.

Yes, I happen to have a few skills that, when combined, apparently result in epic stuff happening, however, like all of us, I have a heap of skills that have no relevant application to success whatsoever, but I appreciate them anyways. Like being able to whistle from the side of my mouth, conduct a paintbrush to do some pretty good face painting for our kids or being able to pick a great horse to bet on in the ninth race at the track.

The key to winning two years in a row can be simmered down to just this: I am willing to go at something a second time, even if it means I might not finish as well the second time.

The first win was amazing. After I won it the first year, no one believed I would apply again the second year because they did not believe anyone would want to see themselves sliding down the list.

"Who wins two years in a row?" is what the doubting voices in our minds whisper at us repeatedly in these kind of situations.

After all, do we really think Miss America likes handing her crown off to the new Miss America? Heck no. Who wants to be last years Miss America and have to take the stage?

Best to fade into the woodwork after a win. "Go out on top," as they say.

Here is the golden nugget -- if you never try again, you will never know if you could have done it better, bigger, different.

So many times we do something well then stop right there because we love the comfort that success gives. Why test it?

I take the opposite view -- why not test it? What is the worst thing that can happen? You could be last year's Miss America. But what does anyone really expect? Who is truly judging you most harshly?

Don't be so afraid of your own abilities and your own judgment.

If you do something well, don't stop there. Do it great. Then do it again and try to repeat your personal best.

After all, we all have a personal best, but is it the best unless we have tried more than once? Who knows, you might take the crown if you actually tried beyond your own perceived limits, if you stretched comfort in pursuit of proof of possibility.

Why not try?

In the spirit of pressing personal bests on stage,

Kelsey xo

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