Lawful, neutral and chaotic - these are the character alignments in Dungeons & Dragons, Shadowdark and many other games. While players can assume any of these alignments in theory, many of my groups fall into the chaotic category. They prefer to break things, go off track and subvert expectations. If there is a mysterious noble in the corner of the tavern, they steal his money, castle and romance his future wife before even listening to the quest he was going to tell them about. If there is a powerful dragon bending them to its will, they would rather die in a senseless fight then getting on the quest.

Your players might not all fall neatly into that category. But I am sure that you have or had at least one of these players in your group. This is not a problem in and of itself, but there is a throughline can make them a headache at the table.

Chaotic players are hard to prep for

On the one hand, chaotic players are great. I love anti-authoritarian themes and am on board with stealing from nobility. But on the other hand, this makes it hard to design quests or predict their actions in a given session. I like to improvise, but I do not want to improvise all of the time. If I prepare a session about being guards at a nobles ball, I do not want them to goof off and bother a dragon each time.

Luckily, there is a method that enables one to steer a group in the same way a lawful quest giver would do. If they always do the opposite of what they are being told, this makes them somewhat predictable in a different way. You can use this to you advantage through the power of reverse psychology.

Reverse Psychology

Say your players will not listen to the quest of an arrogant noble, but will steal from him easily. You could now have the nobles quest have obvious opportunities to do just that. Asking the players to guard his treasure chamber against the thieves guild during the ball reeks of criminal opportunity. If you then casually drop that most of the guards are busy keeping the princess imprisoned, so that she may marry him to further his status, this is sure to draw their attention. If you are especially cheeky, you could suggest that the princess is more interested in a character archetype one or more of the player embody.

This way, you have a mission that is interesting and works if the players play it straight, but even more so if they "break it". By telling them all the interesting things they are not allowed to do, you may motivate them to do exactly that.

Forbidden Areas

Similarly, you can prompt players to go into an area by making that area forbidden. Nothing will lure in a chaotic player more then a couple of guards and a high fence. Whatever you place on the other side is sure to peek the chaotic players interest, which might be the opportunity to finally get to talk about your (super secret, not for the players to know, definitely not open this) worldbuilding.

Making your world slightly resistant to players poking around is easy to implement and gives players the feeling to go "off track", which is one of the things you can only fully do in TTRPGS in comparison to computer or board games.

Artwork by Roselysium for my upcoming book 'A Witches Guide to Grimm's Keep Academy', where reverse psychology is frequently used to motivate rowdy pupils

Multiple Paths

One reason your chaotic players go "off track" might be that they want to feel in control. If there is only ever one quest to go on, or one quest giver to adhere to, they might feel like you are steering them in a certain direction.

If you offer multiple paths by default, they can choose the path they like more, giving them that feeling of control without needing to break things. If we go back to the example of the noble, you could have a noble and the thieves guild giving out a quest for the ball - one to protect the vault, the other to steal from it. In this circumstance, you have covered both possible groups of interest, with a choice so irresistible that the players are likely to do one of them. 

You usually want to relate these paths to the same event or area to minimize your preparation time, but they should differ in their vibe and type of mission to offer variety. Having the choice to protect vault #1 or vault #2 is more boring then the choice between protecting vault #1 or stealing from vault #1.

Conclusion

Reverse Psychology is a powerful tool to steer your more chaotic players into the desired area of gameplay. By banking or their contrarianism, you can predict their movements more easily. You can hatch your bets on multiple, wildly differing quests, that ultimately lead into the same area of gameplay to minimize your preparation time.

If you are interested in more articles like this, be sure to stick around and read some other articles on this blog! I have just released an article talking about the best dungeon you never played, which uses the power of reverse psychology to encourage it's exploration.