It has to be a challenge to keep the strip fresh and interesting for yourself.

It seems to me that most strips evolve over time. Bloom County introduced new characters over the years. Etc.

Help Desk is a wonderful strip. I'm sure you're very proud of it.

But if it gets to be annoying, take a different tack. Try introducing a new story line or characters. Have someone go on vacation or sabbatical for a while. Follow someone to their local big box retailer. What's The Boss's wife like? Who's being groomed to succeed The Boss? Where did The Boss go to school? Have them go to training for something. What's the Y-Box going to do to Ubersoft? Shouldn't Alex be going to night school?

My sister-in-law's boss is a Princeton graduate. He only likes to hire Princeton graduates. He's not to kind to people who work for him who aren't Princeton graduates....

Best of luck. Hang in there...

Cheers,
Scott.