“Whatever you do, or dream you can, begin it. Boldness has genius and power and magic in it.” — Johann Wolfgang van Goethe

When I think back over my life so far, the things I’ve accomplished, the truly remarkable things of which I’m most proud, have, without fail, been those things I was most scared to do. Every one of them seemed, at the time, to be a wild and crazy idea with catastrophic consequences of failure. Every fiber of my being was telling me to run and hide under the covers, to play it safe.

But each time, something in me, perhaps that obstreperous adolescent with the twinkle in his eye and the slingshot in his back pocket who still lurks in my soul, dared me over the cliff edge. And more often than not, it worked.

Sure, I’ve had my share of times that I fell flat on my face in an ignominious heap.  But each time I’ve managed to get up, dust myself off and carry on, all the wiser for my sorry splat. And the wisdom that I gained didn’t keep me from trying again. Instead, it helped me refine my leap, fine tune the risk and increase the chances of success.

Living without regret

I’ve heard countless stories of men and women who, as they near the end of their lives, say that they don’t regret any of the things they did. Much more it’s the things they failed to try that leave them wishing for another turn at bat.

Some time ago I was asked to speak to the senior managers of a company at their annual retreat. The speaker I followed was their liability insurance provider and by the time I walked into the room, there were 30 adults whimpering for their Mammas, having just heard – again – how many ways there are each day to mess up, go broke, end up in jail and otherwise ruin your life. Took me a while to breathe some life and a measure of optimism back into them!

Are you afraid of risk?

By the time we reach a certain point in life, most of us have become trained, professional, risk avoiders. We’ve been shown a thousand ways that things can fail and taught to steer a wide path around the potholes.

Those who make things happen, on the other hand, for themselves and the world, have become trained, professional, risk takers. They know that the best opportunities come wrapped in risk and they get up every morning looking for those opportunities, measuring those risks and excited about the possibilities they see hiding there.

There are two ways to play a game. You can play to win, or you can play to not lose.

Playing it safe, avoiding the risks, working to offend no one, is playing to not lose. In doing so we blend into that vast, featureless collection of could-a-been’s. Bland, easily forgotten and perhaps regretful for those things we didn’t try.

Boldness, daring and risk taking

Playing to win, on the other hand, requires boldness, daring and risk taking. The best coaches know that the best defense is a good offense and, unless there are only seconds left in the fourth quarter and they’re up by 100 points, they don’t back off.

Playing to not lose gets you second place. Playing to win gets you either first place, or dead last. Both are memorable. Both are valuable. First place wins all the marbles. Dead last pays the same as second place but comes complete with free lessons.

Don’t fear failure. Fear timidity.