I believe that officially - absent any DougZ modifications, that your std. deviation should only decrease as additional observations occur (
http://research.microsoft.com/en-us/projects/trueskill/details.aspx) - as the system becomes more and more confident of your skill.
You probably need to have taken a college level probability course to make sense of the research article linked above - and even then it's not a light read.
TLDR, the amount it decreases depends on the likelyhood of the outcome. If you were expected to win, and did, your variance will drop (while your rating will increase slightly). If were expected to lose, and won - your variance will still drop, but not as much, but your mean skill rating will increase to compensate.
DougZ has added a bit of rating decay - which increases your variance every so slightly every day. This keeps people from perching at the top of the leaderboard, and serves to model the fact that knowledge about the game increases over time, and someone who hasn't played in a while may no longer actually be as skilled as they were the last time they played.
Among crazy frequent players - who also have a tendency to be near the top of the leaderboard, this has a tendency to reflect how often you have played recently.
Examples:
You have played ~220 games in the last 10 days - your variance: 6.9. It looks like you're a relative newcomer who's playing obsessively, which is why you are higher on the leaderboard than the other players with a mean skill of 42.... because they don't play as often.
For some of the clowns near the top - who (with me excepted) play a decent amount
Headso ~ 350 games! ~ 5.7
WanderingWinder ~ 130 games ~ 6.5
Me ~ 100 games ~ 8.2