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Anyone know of software that can track both work scheduled as well as actual work done on the same calendar? I'd like something that I can use to both plan what I intend to do, record what was done at what time, and use this information to determine whether my planning is off...

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Microsoft Project will do that and a whole lot more. It is fairly easy to get started with and like most Microsoft products, integrates well with other Office programs for easy transfer of data.

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For some free alternatives...

TaskJuggler uses code syntax and allows for some very powerful features and chart/work load generation. Similar output to MS Project:

tj image

I've used this a little bit and can verify that you absolutely can define a project with two "paths" -- planned and actual/delayed. You write the initial project up with an intended set of deadlines and then fill in the actual dates as you progress.

GanttProject is another free task/milestone/project tracking application you can look into.

gantt project

Lastly, Emacs org-mode, while it has a steep learning curve, is quite fantastic for tracking tasks, todos, and projects. It has a rich timestamping abilities, so you can add timestamps any time you want to update a task's status. You can also track time spent on subtasks and generate a clock report, set scheduled/deadline dates for tasks, etc.

For what its' worth, I use org-mode almost daily for work and tracking tasks. I learned Emacs just for org-mode and it has been absolutely worth it. I just put up some keybinding cheat sheets on my cube walls for reference.

Check out some of the screencasts or the page of tutorials for more!

Good luck with your search.

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here is a similar thread, check it. What about suggested Task Coach?

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like Typoknig mentioned, Microsoft Project 2010 is a great tool for project management. If you're looking for tips and tricks on how to best use it, check out their project management training videos and other resources on their website!

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I can't find any training videos there... – Thomas May 4 '15 at 6:07

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