In this panel James Ernest describes what he calls the "crazy train," a risky option always available to the player when the more predictable path seems less enticing. The key word here is option. The crazy train shouldn't be mandatory.
Chaos & Order in Deadwood
James shares an anecdote from the development of Deadwood Studios. Not getting too deep into the rules, but there was once an option to take a difficult tactical path with a high reward, but it required a very high roll in order to complete. So on your turn, you'd roll and maybe you'd get lucky. Unfortunately, if you rolled poorly, you effectively wasted that turn while everyone else moves ahead with their own strategies. In essence, you were stuck on the crazy train.
In the newer edition, you have the option to "rehearse," meaning that you do not roll. Instead you build up a cumulative +1 bonus to your next roll. So you could just rehearse five times until you get a guaranteed success. Or you could just rehearse three times and take your (newly improved) chances. Either way, you get a choice in the matter.
A choice between chaos (in that case, an unmodified d6 roll) and order (a safe, predictable +1 bonus). You can spot variations of this choice in many games. For example, in Ticket to Ride, you may draw two cards, either from the face-up tableau (order) or from the face-down deck (chaos).
Relative Value of Chaos & Order
The value of the orderly or chaotic option is very situational, depending on the current game-state, an individual strategy, and any penalties for taking the wrong path. In my Princess Bride game currently in the lab, the dealer draws one card per player, plus two. (So five cards in a three-player game.)
The dealer then puts two cards face-down and the rest face-up in the center of the table. Each other player gets to draw one card from this tableau for her own collection, then the dealer must draw two from the remaining three cards.
Most of these cards have important resources you're trying to collect, but some also have one, two or three poisons. If you collect over three poisoned cards over the course of play, there are some penalties of varying severity.
Furthermore, the cards collected also determine the drafting order for the next turn and who will be the new dealer, further tempting each player to take a little poison in order to get better position. Thus, the whole game is built on an order vs. chaos choice, the twist is that a player is crafting that choice each turn for the rest of the group.
There is an orderly choice: "I could take one of the visible poisoned cards right now, because there could be far worse poisons in the hidden cards." And there is a chaotic choice: "I would rather not take any poison, and the dealer may have presented the poison card up front as a bluff so he could collect a hidden unpoisoned card when it's his turn to draw."
Choosing whether to be the dealer presents its own dilemma: Order: "I could always go for the first-pick in turn order, which means I'll never be dealer. I'll always get my choice of card, but I'll collect cards at much slower pace." Chaos: "If I'm the dealer, I'll get two cards, but I have less control over my selection. Which cards do I keep hidden, in order to confuse and tempt the other players while I get my own preferred pair of cards?"
Chaos & Order Everywhere?
This isn't to say that all games should have this choice in their core. There are plenty of fun perfect-information games without any chaotic choices (euro games tend to fall in this category). There are also very chaotic games without any orderly choices to be found (simple dice games and party games).
But... If you're ever struggling with where to go with your next game design and you're out of ideas, try adding a choice between order and chaos somewhere in there.