I finally got around to watching the Fyre Festival documentaries and it was shocking how much bad decisions they made. The creator, Billy, was definitely shady but he also seemed to genuinely believe he could get this incredible festival done in a few months.
His criminal decisions aside, the optimism he had wasn't necessarily bad. In many stories of great founders, they all have a ridiculous amount of optimism that their decisions will pay off. Billy seemed to be emulating their optimism without the logic and evidence usually behind it. When he was told something couldn't be done, he insisted it could. Doesn't sound too different from many famous founders stories.
So where is the line between delusional and optimistic? If optimism is necessary for success, how do you know when you're being too optimistic?
What I noticed in the documentary was their optimism without solutions or terrible ones. Can't organise a festival in 4 months? Nah we can do it. Shouldn't host it on the busiest weekend of the year? Nah we'll be fine. Not enough money to pay everyone? We'll find the money somehow and pay them later.
It also probably takes a lot of self-awareness to tell the difference. Optimism can only get you so far. You need to constantly evaluate situations objectively. Optimism can help when the outcome is undefined but when it's almost certain, not taking that into account might cross the line into delusion.