Will his contract be extended for at least one more year or until he retires? Will he race for another team? Back to Sauber?
It would be extremely uncomfortable for him if after all of the warmth and love Ferrari have shown him they didn't extend the contract for at least 2011. But he isn't a 'Michael Schumacher' and expect to stay with the team for a decade or in other positions/departments aside from F1 racing. Although if Coulthard stayed on as advisor/demo driver than Massa can certainly do the same.
Although next year will be very important for him, as it will be a full season after the suprising '09 events and Ferrari will hopefully be competitive. And a championship would be rather nice leverage for his contract negotiations, also to be considered is that since 2006 his WDC standings have only gotten better...
I know it's still 2009 but the future must always be in sight, and the drivers market is pretty interesting.
And with Ferrari continuing their young driver development program that was started in '08, one can only wonder what will happen with the current drivers and who may possibly replace them (in Formula One as a whole too). Finally a Mexican back on the grid after many years of absence?

Your respectful and insightful opinions are more than welcome...