“Fortune favors the bold.”

“Measure twice, cut once.”

Taken in the general sense, both of these nuggets of folk wisdom are applicable in a multitude of situations. But in a way, they contradict each other. Should I just go for it or should I mull it over first? Should I take the contemplative or impulsive approach? The thoughtful or the assertive one? Careful reasoning or intuition?

Like so many other interesting questions, the answer to this one is “Well, it depends.”

Obviously, if you have plenty of time to think about something, you might as well make use of that time to make sure you make the optimal decision, and if you have very little time, you have no choice but to react instinctively. But there can be other dimensions to the problem. For example, how difficult it would be to atone for a wrong decision. It’s generally a good idea to think long and hard before burning any bridges. Furthermore, some situations degrade over time, meaning the sooner you make the decision, the better off you’ll be, but you still don’t want to make the wrong decision under all this pressure.

Deciding between the contemplative and intuitive approach is in itself a decision that that can be made using either the contemplative or intuitive approach. And so can that decision. Sadly, it’s turtles all the way down.

So what can we conclude from all of this? Not all decisions can be made the way a computer would make them, or your stack will surely overflow. The best I can come up with is to develop a heuristic, play it by ear, and learn from your mistakes. Try to strike a balance between the two approaches. The contemplative approach is usually safer, but overuse it and many a golden opportunity will simply zoom past while you’re too busy in your own head. There’s a time and a place for noodling, but not when an attractive stranger is making eyes at you from across the room.