Depends on the structure of your program. When the Maybe represents the return value of some function that might fail, like a "null" in another language, you'll probably try to eliminate the Nothing case fairly soon after getting it on, and if you have several to eliminate you might use the monad syntax to avoid repeated checks. (User input will commonly use an Either or Error rather than a Maybe, so that you have some error status for what went wrong, but the same principle applies.)

However, sometimes a Maybe represents an inherently "optional" part of your data model, such as "a Foo may have zero or one Bar". In that case, you'll probably hold onto the Maybe until the point where you'd actually read and use that field.