"Interesting failure" doesn't mean "no failure," it means failure everyone is "interested in." "Interested in" means "entertained by the occurrence of" and "willing to continue playing despite," among other things. "Everyone" means the players (including the GM, if any) at the table. It does not mean the characters. Characters can hate and rail against failure that everyone at the table is interested in. Edit: and that might be part of what makes it interesting. You can tell when players are "interested in" a failure, when they willingly enter into or bring about situations in which that failure is a recognized possibility, and when that failure looms they will limit their mitigation or avoidance of it to reasonable in-game responses and techniques, rather than complaints and rules lawyering. Not all failures are interesting, and not all situations lend themselves to interesting failure. Coming up with failure everyone is interested in can require a good deal of conversation, both up-front and in the moment. Avoiding situations that lend themselves so heavily boring failure (failure that isn't interesting) that success is the only interesting option can require some forethought and effort, but is quite doable. Sometimes it's okay for success to be the only option, and to be honest about there being no possibility of failure. Sometimes failure is so interesting that no one at the table is interested in success. Character death can be interesting, and it can even be more interesting for everyone than survival would be, but it often is not. Find out what kind of failure interests the people at your table.