Most of my mistakes happened in the tons of flying I did during my 2 years in PHX, where I lived normally a 10-15 min drive to the airport:
1) Runs hit me hard waiting for a Supershuttle to take me to PHX. Of course, it goes superslow on the freeway. Sparing the gory details, ended up going commando on my flight to LAX.
2) Waiting at the Starbucks before security in PHX, casually chatting with my friend on the phone. I lose track of time, miss my flight, am able to pay a bit out of pocket to gt the next one out. Felt like a real idiot for that one.
3) Plan a 5-day trip to Taiwan the week before my wedding so I could reach 1K and have fun hanging out with my new Taiwanese friends. I leave for the airport, giving myself adequate time to make it in normal traffic. Hit major slowdown on the 51 and am too new to the area to know how to take surface streets (which in hindsight was so simple to do). I miss my Wednesday flight to connect to NRT or NGO in SFO, and thanks to a combination of being a Sabbath observant Jew and dateline issues flying transpac to Asia, I can't fly out for another 4 days. My 5-day trip turns into 2 quick days, but I still made 1K, and get op-uped on my first leg back!
4) A year later, hanging out with same friend from #2 in LAS for his "bachelor party," I'm waiting for him to take me to the airport, and HE loses track of time, I grab a last minute cab, miss my flight, have to pay a moderate fee to take the next flight out, and I still haven't told him. Why make him feel bad?
5) On a trip to China, I booked domestic flights on elong.com, making sure I'd get *A credit Shanghai-Shezhen. I end up going to the wrong Shanghai airport, and have to buy a walk-up fare. I triple checked my itin, and to this day still wonder if the website made a mistake. It was probably my mistake, though. I was even more pissed because the original flight would have meant taking that cool superconducting train to the airport.