I'm going a little off road here, but I think one of Anand's tools could be useful here. I think he's got one that tags notes to titlebars of some apps, so then you can jam other notes there, and use it in combo with all this stuff.

Timer Name = 123456, My Project
Total time = 022:01:06 <hhh:mm:ss>
Keywords used = 123456, Google Books, Archive.org
Timer Creation Date = 2014.05.27 09:05 AM
Last Updated = 2014.08.10 09:50 AM
Timer History (max depth = 100 active days)
Format (comma separated): Date, Running Total <hhh:mm:ss>, Day Total <hh:mm:ss>
2014.05.27, 000:00:04, 00:00:04
2014.05.30, 000:25:26, 00:25:22
2014.06.10, 001:04:48, 00:39:22
2014.08.09, 022:00:28, 03:32:04
2014.08.10, 022:01:06, 00:00:38
So I suppose this is the solution for the time being -- or is anyone aware of a tool that combines the features of Anuran ("nag me for descriptive text regularly") and a Titlebar tracker ("record the time spent in your projects' files") into ONE application?
Anuran actually is like "magically useful" for me.
I would suggest rather a better time tracking software from Replicon as it has helped in better time management for our business activities. It got great usability and at the same time can be accessed from any location using a web browser and can be quickly implemented in any office environment.
Try it and you would definitely like it for sure!!
Sorry, but unless this solution reads application window titles and automatically tracks hours based on activity in the respective windows (which I suppose it doesn't) -- it is only one of the many (sorry again) USELESS "solutions" for time tracking and billing which instead only puts another layer of complexity on top of one's projects.


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