Simply click CREATE STORY or CREATE CHARACTER, then enter the results into the game's "Write Your Own Story". You can save the suggestions to TEXT FILE so you can easily share challenges with your friends.

If so, then why not let the GAMEMAKER do the thinking for you?

If you find yourself picking the same characters or settings, why not give yourself a challenge instead and let the GAMEMAKER come up with suggestions for you. GameMaker is an unofficial fan-made tool that can generate a limitless number of random suggestions that you can use in This War of Mine's scenario creator "Write my own stories". It will even make suggestions for custom characters.

It doesn't make the changes for you (you have to add them to the game's scenario creator yourself) but it will suggest a limitless number of random challenges that you can save and share with friends