It's what the chicken does that makes us ponder his motivation. We see noble young men helping old ladies do this in the movies. Crossing the street and getting to the other side is a normal part of an urban existence and also has some amazing parallels to the risks and rewards of the entrepreneur. Now, I should probably point out that these observations are made with the assumption that you don't look at the Walk/Don't Walk sign. I only bring this up because, like in an industry or competitive endeavor, if there is a clear cut sign broadcasting what your next move should be, you're already too late and everyone else is going to do the exact same thing as you.
The things I pay attention to when crossing the street and in assessing risks in business:
The Distance: How big is this street we're endeavoring to cross? Is it a one way? Are there multiple lanes? Is there a median in the middle that can be used as safe harbor halfway across? Knowing how far you're going to have to make it once you take that first step is a huge factor in taking the risk.
The Collision: How fast are the cars approaching? What is the average speed of the traffic flying by? How quickly will they make it to where you are intending to walk? What kind of vehicle is it? You have to know what kind of progress you need to make across the street before you take that first step.
The People: Are you making this gamble alone or are you taking people with you? If you have others that are going with you, do they know the speed at which you need to make it across and can they keep up? Is there someone else lining up to dart across when the moment is right? Are they going to make their move first? Taking stock of who else is impacted by your next move is essential. You have to have total buy in from those with you and total awareness of others that might get in your way.
The Motivation: How badly do you need to get to the other side? Is it a now or never kind of proposition? Are you going to miss out on something amazing if you don't? Or can you wait a little bit and have the same results without as much risk? The timing of your first move is one of the most important decisions you can make. And, sometimes not beginning and missing the opportunity all together is riskier than stepping out knowing you have to move quickly.
Some of the things to do both as a competitive street crosser and as an entrepreneur:
Step to the front of the crowd: Don't ever stand on the curb, take a couple steps out into the street and get a better look at what the factors are. Then, if you see the timing is right, go for it.
Know yourself: Knowing how quickly you can get from standing still to full speed is something only you can judge. Knowing your strengths and your limitations is essential for taking risks with confidence.
Commit to the decision: The worse thing you could possibly do is take a few steps out and decide you need to go back. By the time you slow down, turn around, and endeavor to make it back to the curb, you'll have put yourself and anyone around you in more danger than if you'd committed and push forward without looking back.