I saw some mention of this in a search but no threads directly about it.

I consider this to be my biggest grappling weakness. My defense from the guard is pretty good but I have trouble making anything happen from here. I end up in guard a lot because most of the guys I train with are bigger by at least 20 pounds.

So what kind of strategies or techniques can I use to improve my ability to mount an offense from the guard? Or should I be doing something else entirely like trying to work for a different(better) position?

what do you WANT to happen?

Keep attacking.
People go into a defensive mindset when they end up in guard, when they should be using it as a springboard for an offense.

basically, get pro-active.

Judo chokes from the guard?

The best fighter in my school completely destroys everyone with omoplatas from the guard. So many omoplatas. So many... He also transitions from failed omoplatas to armbars and triangles, and if those give him trouble, back to the omoplata. I would recommend getting a good sweep game from the guard, since they are good for setting up attacks, or, you know, getting you out of the guard.

Omoplata ( fucking name) is great do to off a triangle or arm bar attempt.
I'll see if I can post some pics of chokes from the guard ( judo aka gi chokes).

Are you speaking offense in terms of striking from the guard, or not?

What is an omoplata? I have heard it mentioned many times, but i have no idea what the hell it is.

Here is one version:

I feel pretty stupid but where exactly does it hurt?

Ok for example, I can get a Gi choke from guard pretty well, but I never seem to be able to sink an armbar or Kimura.

I try to do one of three things in order to setup my offense from the guard-

1. Kip them forward so they are forced to plant an arm, then attack said arm - armbar, kimura etc.

2. If they lean too far back, sit up quickly and try to push them into mount. This usually works well for me once my opponnet is too careful about getting kipped forward.

3. If they get too far down, DO NOT LET THEM SIT UP AGAIN. Make them pay for that **** if you can by pinning them down. From there you can sometimes get the back or get a choke.

Originally posted by WhiteShark
Ok for example, I can get a Gi choke from guard pretty well, but I never seem to be able to sink an armbar or Kimura.

You wanna do THOSE from the guard?
Kimura I can see doing, if you get his weight forward and plated on his arm(s), as for the arm bar, you're gonna have to do pretty much the same thing and fake a triangle, and instead of going for the head, go OVER it and lock around the shoulder, twist your body so that you are stomach down ( don't let go of his locked arm), and you can do a "reverse arm bar" like that by arching you back.
But a "conventional" arm bar, you gotta get him on his back...

something like this:

Here is your Kimura from the guard:

Originally posted by omega
*ahem..leglock...ahem...video...snif...

I hate fighting from guard.

Oh shut up! I know I'm not at your level, besides I saw it coming and started to switch my feet, I just wasn't fast enough! And in my defense that is the first time I've tapped from guard in about 6 months.