The Downtime Project is a pretty interesting podcast that covers some large outages and discusses their post-mortem analysises. Worth a listen IMO, very interesting stuff and some good lessons to learn.

Crashing and burning (in a non-production environment) is an excellent motivator to develop necessary skills; being unafraid to break things and fix them when they inevitably break helps you get a deeper understanding of how the systems work, for what it’s worth.