Wing It? Or Must outline?

[Proto Man]

Typically I plan out major events, and main plot progression I'd like to produce with my posts, but I always have some form of random inspiration or idea midway through the post that alters or adds to my course of action. Then there are times when I'm on a roll and just throw out whatever comes to mind, refining it once I'm finished by either taking away or incorporating additional parts.

One stipulation I try to keep in mind is that if I'm not enjoying writing it, people likely won't enjoy reading it.

^ This. I normally have the big events planned out, but the stuff that happens in-between I tend to just go with it, seeing what inspiration I have. Sometimes, as Luffy said, I get on such a roll that I shift around the big plan to accommodate.