I just re-imaged my work machine and for the last couple of days I’ve been bringing it back to life, installing the various thousands of millions of applications that I use on a regular basis to do that thing I do. This time around, though, I’m doing a little experiment.

Before I re-imaged, I was very careful about organizing my Start menu so I could find things. I created a group called “Programming” to keep the various IDEs and development tools I use in, and subgroups for various functions therein. Same thing with programs that work with multimedia stuff (Flash, Photoshop, etc.) - I had a group in the Start menu for that.

The problem is that installers don’t always let you select where to put the icons in the Start menu. Most times, they just create their own company-centric Start menu group, then create a product-centric group under that, then create their one program shortcut inside that. That means I end up installing the program, then manually opening up the Start menu and rearranging things to fit my usage. You know what happens then?

I upgrade.

I take the latest stupid version of whatever stupid project, I run the upgrade installer, and the damn company-centric Start menu group comes back. And the product-centric group inside it comes back. And the same single damn program shortcut comes back. And I, once again, have to go through the rearrangement of icons to be more sensible. This time, though, it’s a manual diff-and-merge process, trying to determine if the old icons still work or how to replace them properly with the new icons.

You know what’s worse? Nothing could be worse, right? No, there is something.

Uninstalling.

Now I’ve got icons in my personally organized Start menu that don’t point to anything. I have to manually keep track of these things or find a program that will run through my Start menu and remove shortcuts that don’t point to anything. Argh!

Why haven’t we figured this out yet? The Start menu’s over ten years old! Installers should let me specify where to put shortcuts if I opt to even create them. If the developer feels the desire to suggest a default location, perfect - users who don’t care can make that extra click on the “Next” button and there’s no skin off their noses. But if I want to override that, and have everything organized, I can. And maybe I don’t even want to create icons - let me uncheck the little “Create a program group for this program” option and carry on my merry way.

I mean, tell me it’s not just a company’s big brass balls thinking that they need a whole program group just to themselves and that, should I deign to buy more of their products, I will inherently want to group the products in my Start menu by manufacturer and not by functionality.

I don’t actually think this will change, not in my lifetime, but this is the sort of thing that irks me. As far as my experiment is concerned… I’ve installed maybe 15 things thus far and my Start menu already wraps into a second column. Unreal.