Strategies would be different for an individual as opposed to societies. Both would as a first approximation only be as cautious as they need to be in order to preserve themselves. That's where the difference between local and global disasters comes into play.

A disaster that can kill an individual won't usually kill a society. The road to progress for society has been paved by countless individual failures, some of which took a heavy toll, but in the end they never destroyed everything. It may be a gamble for an individual to take a risk that could destroy it, and risk-averse people will avoid it. But for society as a whole, non-risk averse individuals will sometime strike the motherlode, especially as the risk to society (the loss of one or a few individuals out of the adventurous group at a time) is negligible enough. Such individuals could therefore conceivably be an asset. They'd explore venues past certain local optima for instance. This would also benefit those few individuals who'd be incredibly successful from time to time, even if most people like them are destined to remain in the shadow.

Of course nowadays even one person could fail hard enough to take everything along with it. That mat be why you get that impression that rational people are perhaps too cautious, and could hamper progress. The rules for the game have changed, you can't just be careless anymore.