There seems to be a bifurcation in the way people approach new initiatives. There are those that get an idea, roll up their sleeves and get to work, because action is better than inaction, even without much preparation. These are people that get in their car and go, possibly driving north to get to the South Pole.
Then, there are those that prepare so much that they never take a risk. They try to take every uncertainty out of the equation, but never get to the point of feeling confident enough to move forward.
In a time where the mantras of Do the Work, Ship it and more seem to be at opposition with the Boy Scouts (i.e. Be Prepared), I think the reality is that you need both.
If you fail to prepare, you prepare to fail. But at the same time, if you prepare indefinitely, you never get past the preparation stage. So, as a happy medium, do both.
As Tim Sanders reminded me in a recent tweet, Abraham Lincoln once said something along the lines of that if he had 8 hours to chop down a tree, he would spend 6 sharpening his axe blade (and I am hoping that he would have spent at least a few minutes making sure that it was the right tree or his neighbor could get really pissed off). But the key element is that he had a plan for moving from preparing to doing. If he spent 8 hours sharpening the blade, the tree would still be standing.
Stack the odds, and then take the risk. It’s not an either/or proposition.