I have this problem with contests. No matter how many entries or the strength of my competitors, I’m always certain that I’ll win. An all-expense-paid honeymoon in paradise? The prize is practically ours. Lifetime supply of dog treats? Only a heartless monster could resist Jasper’s lopsided ears.
But then there’s my other problem with contests: my certainty is completely and utterly ungrounded. I never win. Until last week, that is. And holy shnikes did I hit the jackpot.
Earlier this year, my quirky little workplace was acquired by the behemoth that is Deloitte. Going from a company of 150 to a giant worldwide partnership has been a bit of a culture shock, but it hasn’t been without its perks.
One such perk: a blogging contest (topic: leadership in action) with a pretty amazing prize. Minutes after the announcement hit my inbox, I was already planning my summer around a trip to the London Olympics. Because it was obviously meant to be. Yeah, right.
Tricia, founder of Heroes for the Homeless and an all-around lovely human being, was the obvious subject of my entry. For the past seven years, Tricia has exemplified leadership in action—day in and day out. As founder/director of Heroes, Tricia runs an entirely volunteer-driven non-profit that provides food, clothing, emergencies supplies, and support to homeless individuals in the greater Seattle area. If that’s not leadership in action, I don’t know what is.
And somehow, Tricia’s story won. (Yes, I may have shamelessly promoted my entry on Twitter and Yammer, but that’s mostly beside the point.) And I learned that the misguided hope of winning a contest and actually winning a contest are two very different things.
So I’m going to the Olympics. In London. Thanks, Uncle D[eloitte]. As they say on the other side of the pond, bloody hell.

I have similar experiences, only usually I only know that I’m going to win something I have absolutely no use for.
Haha—that too
My all-time favorite prize was an All Dogs Go to Heaven lunch box that I won from the library as a child. Totally amazing.
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