OmniFocus Do Over

Hi. My name is Gabe and I have a problem with planning.

Now that I’ve gotten that off of my chest, the healing can begin. I use OmniFocus to manage tasks. Well, to be honest I use OmniFocus, Outlook Exchange, Simplenote, post-it notes, lipstick on mirrors and full body tattoos.

One major issue with tracking tasks, as I have lamented many times before, is that I work on Windows all day. That means there is no OmniFocus clipper or quick entry box. I’ve rigged my email to add tasks to OmniFocus and I still love Spootnik, but both methods have just enough friction that I’ve relaxed into adding tasks in Outlook and relying on iOS sync and reminders. This is not a good system. It’s low friction getting things in, but it feels like a third degree rug-burn getting them out.

Carrot and Stick

So what’s my motivation for this self-intervention? I have just embarked on a large multi-year, big-dollar project at work. Perhaps the biggest project I have ever managed. There will be dozens of people, thousands of tasks, hundreds of goals, and dozens of milestones. The challenging part is that there is only one deadline and one successful end-point. So I’m left with two major motivating factors.

Carrot: Make my work easier so I can unplug when I’m at home.

Stick: Keep my job.

The Do Over

I cleared my OmniFocus inbox. I deleted old projects. I removed tasks that were postponed. I stopped lying to myself. Now for the hard part. I have to stick with a new system.

The Plan

While I may be stuck with Outlook and MS Project during the day, I have the gang at Omni Group to back me up. OmniPlan can import and export MS Project files and OmniFocus has the best iOS apps available. What I really need is the quick clipper functionailty available on the Mac but on Windows. I have something I’ve made but it’s still in the testing phase. I’ll post more on it later.

I’ve made a sizeable bet on the future of OmniPlan for iPad. The Omni Group are estimating a Q2 delivery for OP on iPad so I went ahead and spent the $200 for OmniPlan on Mac. I wanted a head start to get going with OmniPlan learn the system and limitations on my Mac before trying to rule the world from my iPad.

Work Ahead

I already have custom tools for sending tasks to OmniFocus from Simplenote. I use this mechanism far less now that the iPad version of OF is so outrageously great.

The lack of a Windows version of the OF clipper can be compensated for with the email support on my Mac server at home.¹

I want to rework both of these mechanisms to support attachments and inserted images. I also want to try making an Evernote to OmniFocus script. I’m not sure why, but it sure sounds fun.

Unfortunately, Spootnik has not received an update in a long time. It is still quite good, but it’s no replacement for sitting in front of my Mac. That means I need to do more with OmniFocus on my iPad and my server at home. Hopefully, before the stick mentioned above is truly a threat.