Writing holistic characters is actually an interesting concept I've come across since first being introduced to Dramatica, but I can't help but feel I run into a roadblock since many of the situations I come up with tend to be linear, having a straightforward objective and a list of necessary steps to achieve it. And then I drop the holistic character right in the middle of it and perhaps unfairly ask her to deal with it. (My holistic characters all tend to be female).
For example, I wonder how to write a holistic assassin, because I can't help but see the task in a linear fashion. (1) Get the target in a position where you can kill him and (2) kill him.