In 2006 I decided to try to bike around the world in 365 days... Starting on April 20 2006, my only official goal was to be back on April 19th 2007 for my mom's birthday. The second (secret) goal was to reach 40'000km on the bike during the trip, but I didn't tell anyone as already everybody thought I was crazy to go around the world on a bike...
The plan was fairly simple: Go east until I reach the Pacific then fly to Alaska and go South all the way down to Argentina, and then fly back to Europe. I didn't organize much except for a 2 week intensive Russian course in Vladivostok at the end of May. The may issue was to get a business visa for 3 months in Russia, which needed an invitation from a Russian company and a couple of trips to the Russian embassy in Bern. The only other thing I organized upfront was a flight from Costa Rica to Ecuador on November 30, forcing me to keep moving forward and reach a deadline about half way through the trip. All the rest had to be organized during the trip...