I approach every flight with Murphy's Law front and center.
I anticipate that things may go wrong, and I carefully weigh my options should that occur.
Do I book my travel so I'll be able to get to the airport way early? You bet. Do I get to the airport way early? You bet. Do I have the CS phone numbers programmed into my Treo? You bet. Do I have flight schedules for both my primary carrier and alternate carriers available? You bet. Do I track which gates my arriving and connecting flights typically occupy, and the distance between them? You bet.
In spite of all this, have I encountered situations I hadn't planned for? You bet.