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In my family, when we’re making a high-risk decision, we ask ourselves, “If I fail, will it make a good story?” Since I’m a storyteller by trade, we usually respond with a resounding, “Let’s do this thing!” Hence, the sailboat* and a dozen or more other precarious life choices.

When you make decisions based on security alone, you trick yourself into thinking that life can be controlled, the forces of nature can be tamed, the laws of the universe can be mastered. But even the safest life is fraught with risk – we just don’t acknowledge those risks. We prefer to avoid making eye contact with the hundred ill intended possibilities lurking in the shadows of every room.

It’s important to keep this in mind when making decisions about your life’s course: Failure is unavoidable. Danger is around every corner. Death in inevitable. 

While that may seem like a particularly fatalistic viewpoint, it’s actually liberating. 

When you make decisions based solely on the illusion of security – whether it’s securing your physical person or your reputation or your status or your money – you’re often forced to pay a price. Usually, that price is your heart’s desire. And the truth is you’re still no more secure. You’re only more dissatisfied.

Even if you’re 100% selfless and completely on the up and up at all times, people can concoct wild stories about you. Even if you always wear the right shoes and use the most up-to-the-minute catchphrases, you can still be abandoned by the cool crowd in favor of someone a smidge cooler. Even if you pinch all of your pennies and tuck yourself safely in a padded room, trust me, a disaster can befall you and clear out your bank account and your health.

And you’ve still not done what you want to do.

Wouldn’t it be better to face your fear and your desires honestly? To give equal air time to both? To pursue that wild dream in the face of risk? It will be so much sweeter if you achieve it, and even if you don’t, you’ll have a more interesting life story.

*Statistically, it’s far safer to live on a sailboat than to drive five miles to work. Weird, right?


P.S.If you’d like to read about my harrowing failures as a sailor, I’m documenting some of them at Not all of them. I don’t have that kind of time.