Scotland missed out on a place at Euro 2012, meaning that they still haven't qualified for a major international tournament since the 1998 World Cup in France.
However, Caldwell believes that these failures will help spur the Tartan Army on in their bid to qualify for the 2014 World Cup in Brazil.
"With every campaign that goes by the next one becomes more important and as a group of players we have to live with that, it is down to us," the 30-year-old said.
"We have been part of the campaigns that have failed but that only drives you on to want it even more. So we have to use the pain of the last campaign and take it into this one and make sure it doesn't happen again.
"Personnel probably hasn't changed a great deal but the manager knows the group a lot better than he did in the last campaign, he knows what tactics suit us. So we are far better prepared to go into the qualifying campaign than the last time."
Caldwell will win his 50th cap for Scotland against Serbia tomorrow before going on to face Macedonia on Tuesday.