Task example A: "Mindmap project for insert work-related project"

Task example B: "Read Batman #15"

Despite the differences between these 2 tasks, there is one thing in common: they both have the context "iPad".

Unfortunately, like a lot of folks out there, I have to live my life as two different people — my work self and my real self. When I'm at work, certain things are expected of me. Things that I'm supposed to do and things that I'm not supposed to do. I've also accumulated many different types of "hats" while I'm at work.

When I'm my real self, or the actual me, I get to wear all the other hats that I've accumulated in my personal life.

Husband. Father. Nerd. Condescending jerk to my friends. Comic book reader.

Every single task that I have in OmniFocus belongs to either a personal hat or a work hat. It may be confusing and overwhelming to juggle and maintain the hats that we've accumulated in our lives, but for me, there is one thing that is consistent.

Wakeup - 5pm on weekdays is the only time where I will recognize my work hats.

Assigning Times

In an earlier post of this OmniFocus series, I stated that contexts were "the single most useful piece of metadata one can add to their task list"2. While I still believe that to be the case, start dates are definitely a close second in terms of use. I found that filtering my list by both contexts and start times in OmniFocus has successfully changed my ability to complete my daily tasks.

So how do I go about this? By following this strategy.

Start Times Flowchart


Fortunately for me, there are some things that I can get done at work despite whether the task is work related or not. Examples include answering a personal email, brainstorming a personal project in a notebook, call optometrist to schedule an appointment. So for those tasks, I will set them to start at 12am on a given day.

Why 12am? Honestly, because that’s what OmniFocus is set to by default. No real magic there. Fortunately, this also works out because when I wake up in the morning, looking at OmniFocus can give me a heads up as what to expect before getting into the office.


Now there are those tasks that either 1) require resources which aren’t available at work (e.g. my Mac Pro at home, coffee grinder, tools) or 2) really should be tackled on my own time. Examples of these tasks/projects include: setting up Hazel rules for nerdy personal project, read comics, prepare steak dinner, shave. When a task like this appears and I want to tackle it on a weekday, I will set the start time to 5pm. Pretty explanatory why I chose 5pm — but just to be clear, that’s the moment I hang up my work hats.

Only Two Start Times

12am and 5pm are the only start times that I choose. The reasons for this are pretty simple:

  1. I don't have OmniFocus in front of my face every minute. So if something pops up at 3:30pm, it doesn't really matter.
  2. If something needs to be done by a certain time, then that's something that either needs to have a due date assigned and/or belongs in your calendar.
  3. I like to work ahead, so I like to see all tasks available.

The Future

While setting the actual start time will definitely help in showing what I can absolutely do at the moment, I also make heavy use of the actual date.

For example, I work in two offices. Sometimes there are tasks that only can be done in one of those offices. Let’s just say that the end of the work day has come for me, and I think of a last minute task that I need to do in Office A. I will set the start time to 12am on the day that I know I will be back in Office A. Not only do I avoid seeing it while I’m in Office B, but I will be able to see it pop up before I actually commute to Office A (via 12am start time) so I still get the heads up.

Another example is dealing big personal projects. I tend to hold off on these projects until the weekend arrives so that I can devote more time to it. If I come across one of those potential weekend projects, I will set it to start at Friday at 5pm.

Adding Flags to the Mix

So I have my contexts and start dates all set up — now comes the pieces that glue everything together, flags and due dates.

In my previous post, I mentioned how I use flags to denote intention while due dates are hard deadlines with consequences if not respected. My daily driven perspective (named Core - Contexts inspired by the great book, Creating Flow with OmniFocus by Kourosh Dini) shows me the following:

  • Mode: Context
  • Grouping: Context
  • Availability: Available
  • Status: Due or flagged
  • Estimated Time: Any duration

To "flesh" that out into words, this perspective shows me anything that is flagged or due that day with a start date that is either today or prior1 and a time that is now or prior.

In other words, it shows me what’s available now and that I have intention of doing or that needs to be done.

Processing and Planning


Whenever I process my inbox, if I don’t do the task on the spot, then I will typically add a context, a project (if available), a start time (if available) and a due date (if available). If I have no idea when I intend to work on a given task, I will leave the start time blank.


Part of my goal in doing nightly reviews is to

  1. Make sure projects don’t get stalled
  2. Pick out tasks that I intend to do or have an idea when I can do them

So I go through each project and make sure at least one of the tasks has a start time/date and a flag, in order for them to show up in my perspective at the appropriate time. I also go into my one-off task list3 and pick simple tasks that I intend to do. As with any other task, I will assign a start time/date and a flag.

Looking at it, one might see that the use of start dates and flags might seem to overlap each other in terms of responsibility and functionality. But there’s one key thing about this that I absolutely love and actually helps me out a lot.

Tracking Start Times

Let’s create a task: Research on how to build a Turbo Crazy Roaster.

Now let’s set it to have a start date of today at 5pm. Flag it — since I intend to do it (no consequences if I don’t).

So I come home from work and I come to find out that I am actually expecting last minute guests that night and will have to put this off. So I change the start time to tomorrow 5pm.

Let’s just say that more plans come up for the next few days and that I don’t have time to do the research. At that point, I’ve been consciously pushing it off and I know that it has been neglected in favor of more important/urgent tasks.

At some point, I may think to myself that I don’t really have the time for it at the moment — in which I’ll unflag it. The act of unflagging is important because it means that I don’t have any intentions of doing it at the moment.

During my nightly reviews, I will eventually come across that research task. However, this time it will have the last start date that I set it to have. Meaning, that the last start date that is still attached to the task indicates the last time I intended to do that. This not only gives me a pretty accurate glimpse of any task that I intended to do at one point, but how long I have put it off for.

What this also gives me is a way to indicate what task hasn’t been “promoted” to my Core - Contexts perspective. A task that hasn’t made it to the perspective will have no start date attached to it.

Seeing tasks with old start dates or no start dates (for a period of time) gives me an indication that I haven’t devoted enough intention to complete the task. This aids me in everybody’s favorite part of productivity — dropping the project/task.


Before I drop the task, I take the time to analyze the task and see whether it is a mini-project in disguise. I have noticed that a lot of the tasks that I lack motivation in doing can actually be broken down into smaller micro tasks. This has been successful for me in getting over the psychological roadblocks I set up for myself.

Initially breaking down a project into individual tasks is not my specialty.


I believe start dates is one of the most undervalued features in OmniFocus. However for me, the way that OmniFocus handles start dates is the number one reason why I use the app. Effectively hiding the task when I don't need it and having it appear when I do is what I believe is key in a task management app. With contexts and start dates, OmniFocus is a winner.

  1. Blank start dates will also show too. That'll be for another post. 

  2. Yup, just quoted myself.  

  3. Project organization will be an upcoming post.