Gamble Big . . . On Yourself

Native Detroiter and star of Comedy Central’s Key & Peele Show, Keegan-Michael Key has been back in Detroit a lot lately.  First to help open Jack White’s new shop in downtown Detroit and again as star of a benefit show at the DIA to help raise money for the Detroit Creativity Project, a project to bring improv into Detroit middle and high schools.

For those of you who have not seen his show, check it out.  It’s really funny.  But, this post is not about his show, rather it’s about his quote on his career:

“It’s quite amazing when you gamble on yourself, things can go your way.”

Now, it’s easy for Key to say this since he’s had so much success.  But for those afraid to take that leap, living his words can be difficult.  Especially because our society is too quick to criticize failed risks, instead of thinking of the failure as one step closer to a success.

Unfortunately, those who avoid risk view failure as a cost, a loss, a negative.  But often, there is this same cost or loss by NOT taking the risk.  An example might be, you don’t want to risk opening a your own business because it might fail.  But what is you reversed the question and asked:  Is owning my own business worth the risk.  Or, is it a risk to just keep going to the same job day after day.

Here are four ideas that might sway you to gamble big on yourself.

First, we always, always, always, (and did I say always), regret what we did not do, rather than what we did do.  Personally, I’d rather ask for foregiveness than ask for permission.  Yes, it gets me into trouble, but only by pushing the envelope do I find out what I can’t accomplish.

Second, remember, someone else is always taking a risk on you.  Your employer takes a risk on you everyday, hoping you’ll show up and do a great job.  Every driver on the road is taking a risk on you, hoping you will not cause an accident.  Your credit card company takes a risk on you assuming you will pay your bill off on time.  Everyone else is taking a risk on you, why not take a risk on yourself.

Third, one of my favorite quotes on risks is from management guru, Peter Drucker:  “People who don’t take risks generally make about two big mistakes a year. People who do take risks generally make about two big mistakes a year.”  Most of the time what we fear may happen never does.  And, even if you avoid taking risks, you are still going to make mistakes.  So, you might as well make mistakes on your own terms and on your own intentional decisions.

Fourth, start with a small gamble.  Ask for a promotion; even if they say no you are no worse off than if you did not ask.  Ask for a raise; again if they say “no”, you aren’t any worse off.  And, they might just say “yes”.

Share with me your big gamble and what you want to achieve.