I've often said that THE most difficult part of our three-year journey from Alaska to Argentina was making the decision to take it. Once the decision was made, it was a piece of cake. I've got a page on our website where I talk about making the decision - all the top articles are more geared toward family travel, but scroll down to the box at the bottom and I've got 10 or 15 links to other long-term travelers where they talk about making the decision to head out.
http://familyonbikes.org/resources/decision.htm