Task Management Software Mess

Posted by mitch on August 04, 2010
productivity, software

Last night, I was ranting on Twitter again.

This time it was about task management software. There’s several options out there, but everything I’ve looked at has fundamental flaws. I’ve settled on Remember the Milk for now, but I’m not thrilled with it.

Here’s what I want:

  • A clean UI that is fast and optimized for brain dumps of a large number of tasks. Smart tag management.
  • Mac-native application.
  • A web UI for when I don’t have my Mac handy.
  • Storage in the cloud and locally. I want to use it when the cloud is down, when my connection to the cloud is down, on the subway, etc.
  • I don’t want to bring my own cloud service. I want to buy a service that someone else runs.
  • Integrate with Google Apps: My calendar should show deadlines, the task system should have access to my address book, etc.
  • Good iPhone application with emphasis on new task capture and the ‘next’ to do list.
  • Nice to have — Outlook for Windows plug-in to sync tasks into Outlook’s to do. I use Outlook 25% of the time for Xobni.
  • Nice to have — Integration with BaseCamp. I don’t use the To Do stuff there much, but people assign me tasks in BaseCamp. It would be nice to see those in my To Do list (and be able to click to go to them in BaseCamp).
  • Nice to have — Integration with Salesforce. Again, tasks are created in Salesforce and I’d like to see those in my central view of the world (and be able to click to go to them in Salesforce).
  • Nice to have — Show today’s calendar item from Exchange / Google Apps. This is particularly important when planning what to do next and identifying how much time I have from now until my next commitment. I often flip back and forth between calendar and the to do list. Neither Outlook nor Google Apps get this view right.

Here’s what I’ve tried:

  • Things — I have bought Things for the Mac, iPad, and iPhone. However, after it trashed its database and tech support basically told me “I don’t care”, I haven’t been able to get back into it. Fundamentally, it is missing cloud sync, which makes it somewhat useless for someone who travels a lot. My corruption seemed to be related to syncing with the iPhone, which doesn’t inspire much confidence and so I would stop syncing with the iPhone. However, the Things UI is almost perfect. No one else seems to hold a candle to it.
  • OmniFocus — I tried it a few years ago when it came out, but it was riddled in complexity and not as smooth as Things. This might be fixed now. I would like to try it again, but Omni doesn’t offer a production cloud service yet. I generally like Omni products.
  • Remember the Milk — I like that I can use it from any computer. However, it’s tedious for dumping in a lot of tasks. Setting a new location on a task requires a manual step of creating a new lcoation. Why can’t I just type in my own locations and let it sort them out? The details for a task are presented on the right side of the window, rather than right next to the task, which leads to a lot of mousing around. In fact, the whole UI is about mousing around and a lot of clicking. For example, I have a task with some notes. When I click the task, it shows that I have 1 note, but I have to click again to see it. Just show me everything. I’d like something that I can control entirely from the keyboard. However, the iPhone app is quite decent based on a cursory examination. No Outlook integration.
  • Evernote — Not really a task management system, but I had heard of people using it as such. Great for what it does, not great for task management. But the cloud service, native apps, and sync model are all perfect.

I will keep plodding along with Remember the Milk for now, but I’d really like to see a Things-like UI for Remember the Milk, either as a sophisticated JavaScript UI or a Mac application. For busy professionals, task management is a huge tool and nothing seems to get it right. There’s a market hole here that someone needs to fill. Several people have asked, “so why don’t you write it?” I am very busy with another software company right now and one at a time is the maximum for me.

P.S. If you know of a solution that I missed that might work better for me, I’m all ears!

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