I got into a discussion today about why characters have to be empathetic, if not likeable. And the guy I was talking to said he would rather try to break the rule than play it safe. It made me think of Alexander’s quote. I also spent some time talking about the Donner party and marvelling over how many times they were told to turn back. At each point they could have, half the party turned back and went the long route. Some looked at the first mountain range they had to cross, some of them were told by a rider who had just taken the pass and the guy who said the path existed told them twice, once in writing, once in person to go the long way. Each time, more people turned back until it was just a handful of families.
Every wagon that went the long way around in the original party made it to its destination but the Donner Party. If fortune favours the bold and the well-educated*, failure favours the foolhearty.