This was written for a coworker who was bummed out about not being able to go to Pycon this year. The views expressed here are possibly slightly exaggerated for comedic effect.
1) Django people. They are crazy. Avoid at all cost. If you don't know why, go and find a herd.
2) It's held in the same city two years in a row and that city is never Las Vegas. I'll go to Atlanta once. Under normal circumstances, why would I want to go back?
3) You know the people you work with? Imagine hundreds of such people all in one place. Imagine seeing eight copies of yourself in the hotel lobby. Now imagine yourself getting into a fist fight with three copies of yourself. Pycon is mirrored worlds colliding with frightening results and often shards of glass in eyeballs.
4) Guido van Rossum is lazy. The year I went to Pycon his keynote address consisted of him answering questions tweeted to him on a large screen. Would it be too much trouble to write a little something up in advance?
5) Pycon is for networking and schmoozing. Don't expect to learn very much or see too many new things. It's for "pressing the flesh" and what socially awkward flesh it is!
6) All the talk about Python saving the planet (I'm slightly exaggerating) is nauseating. It's a freaking programming language. Get over it. It's not going to cure cancer, it's not going to become self-aware, and it's not going to make you live forever. Other programming languages can be nice too.
7) There are five talks you think look interesting. Four of them are scheduled at the same time. You are able to go to two of the five talks. They turn out to be disappointing and the ones you had to miss were rumored to be awesome. You watch the talks you missed on video later, at home, when they are posted. The audio and video turn out to be poor and the talks really weren't awesome anyway.
8) If you are a single guy and are looking for a cool python chick for a relationship, forget about it. There are attractive women at Pycon. However, they are always mysteriously surrounded by huge groups of smarmy looking guys. Good luck with that.
9) Hipsters. Pycon has them.