1 Iki Piki: We also need to recoup the capital to repay the loan shark. And dropping a large bet on a longshot will lower the odds.
2 Serron: Hmmm. So we should borrow as much as we can and bet it all in order to maximise our winnings. In fact, let's bet the ship too!
3 Serron: Then when we win, we skip the system without repaying the loan! What could possibly go wrong?!
4 Iki Piki: I really don't know...
4 Serron: See! Foolproof!
4 Iki Piki: ... where to begin.

One of the favourite phrases used in the lunchtime "stupid ideas" brainstorming sessions I have with my friends at work is "What could possibly go wrong?"

In some cases these sessions produce worthwhile fruit such as Darths & Droids. Other times they produce ideas that would put Serron to shame. You don't generally get to see those ones.

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2018-07-23 Rerun commentary: I should stress that we don't specifically try to come up with stupid ideas. Rather, we come up with ideas, and we don't mind if many of them are stupid or how stupid they are. If you try to restrict your brainstorming to coming up with good ideas, then it makes people less inclined to share their ideas, and so many potentially good ones can be lost. So it's better to encourage everyone to share everything, and then at a later stage winnow out the bad ideas and identify the ones that have promise.

This is a real strategy used to encourage creativity in business or research contexts, often known as divergent thinking to brainstorm as many ideas as possible, without regard to how stupid they might be, followed by convergent thinking to filter out the bad ideas and narrow down on the good options. But you can also use it in purely creative contexts, such as coming up with ideas for stories or comics or artwork or whatever.

If you do anything at all creative - which includes solving problems of any sort - and haven't consciously used this sort of process, maybe give it a try. Set yourself an initial goal to come up with as many ideas as possible, without caring how good or bad they are, and write them all down. In fact, positively try to come up with questionable or silly ideas at this stage. Then at a later stage, perhaps a day later even, go through them all and think about how good or bad they are. Consciously separating the brainstorming process from the judgement process can be more productive than trying to just think of a good idea up front.