If you're interested in a book about massive failure - read the story of Donald Crowhurst (The Strange Last Voyage of Donald Crowhurst is the book, there is also a documentary out there). It's hard to tell much without spoiling it, but basically, a highly publicized sailing competition was sponsored in the mid 20th century to see who could be the first person in history to solo circumnavigate the globe with a sailboat. Crowhurst had little to no sailing experience, and mostly sold navigation equipment and gadgets for sailing - a weekend warrior - and bet his entire future and business to support his entry into this endeavor. It erm... did not go well, and got increasingly worse, then almost ok.. then absolutely not okay. They don't know what truly happened in the end, but what did survive shows he went mad at sea from the likely pressure he was under.