If failure is a supposedly the best teacher, then I think I’ve assembled an Ivy League faculty here. Conversely, failure is easy - much easier than success - given so many more opportunities. We should therefore be surrounded by excellent teachers. Unfortunately, that doesn’t appear to be true - especially when financial failure, if catastrophic enough, seems to be rewarded. So... I offer some cautionary material that can serve as the “don’t screw up” portion of anyone’s success formula.

If you used software in the 80s and 90s, In Search of Stupidity will be a great read. Why aren’t we all using WordStar, Dbase, and Quattro on CP/M-based PC-Juniors? The answers are all there in tragic (and funny) detail. If you don't really want to buy the book, the site also has some cute examples in “The Museum”. In Search Of Stupidity
This is a study of the classic cartoon that clearly illustrates the abyss that can appear between requirements and an end product. For an IT professional, it’s funny in a depressing kind of way. Tree Swing
Virtualization machines are wonderful.  They install, backup, restore, failover, and rollback better than any "real" system - in fact this site was developed on a virtual appliance.  However, I have often noted that "the more code between you and the silicon, the better the odds of failure”.  This event of 2008 illustrated my point in a rather painful way.  Virtualization “Doh!”
In addition to being really funny, Dilbert and his dysfunctional co-workers are wonderful illustrations of what to avoid in both professional and personal relationships. This is probably why they make money selling reproduction rights for presentations and intranets. Even if you just want to look, you can see almost 8000 strips at the  (just click "Buy" for reprints and licensing)

Dilbert Comics

There’s nothing more irritating than an overoptimistic, cheery, motivational poster when you’ve had a few setbacks. Despair Inc. has an alternative. Their depressingly cynical posters and t-shirts make even small successes seem glorious by comparison. Demotivator Posters
Despair T-Shirts
While it’s pretty common practice to mislead with statistics and cleverly drawn charts, it’s even funnier when a chart's author has no idea what they're trying to say.  This site has a nice collection of weird and uninformative graphics.  Note: Lack of recent updates implies that this site may disapear soon - so look quickly. Ugly Charts