I was thinking about this in the context of people being on the fence about leaving behind pickme behaviour and applying FDS principles.

I think looking at the worst outcome is a good evaluation strategy because it focuses on singular, definable events. Potential positive outcomes can vary much more in how satisfactory/acceptable they are, thus making picking one realistic "best" for comparison purposes difficult.

To illustrate with a dating example: the worst outcome of a walking date would be having no safe and swift way to bring the date to a close as you would need to leave your date's presence on foot, rather using transport, potentially needing to return to the point you started the walk at before you can even start to do so. Meanwhile at a dinner date, you are likely to have your own vehicle or other transport (e.g. uber) swiftly available, you can sneak away under the guise of a bathroom visit if the subterfuge is required for your safety, there are other people guaranteed to be around and primed to pay attention to you (staff). These are unlikely scenarios as you'd hopefully have picked up on any potential safety issues and blocked during the course of vetting but this is about considering your comfort and safety if this failed or you were deceived, by thinking through the WORST. There's too much cultural messaging to be optimistic and meek, and the worst outcomes in doing so are abuse and death.