The Waiting is the Hardest Part

As the late great Tom Petty used to sing, the waiting is the hardest part.

Waiting is an important part of difficulty in finding focus. If we are in the middle of something and then suddenly have to wait, we may wish to start something else, often in the name of efficiency. Or we may have a sense of lost momentum we hope to avoid. Or we may seek stimulation, trying to avoid an intolerable boredom.

Sometimes waiting for something to finish is useful. For example, if I decide to continue sitting there while uploading a file, I may have other ideas about the current project come to mind. Were I to have turned away, I may not have had those ideas.

But turning away may be fine at times, too. For example, I’m not going to sit there if the upload process is going to be an hour long.

It would appear that it is time that would be the decisive factor, but this is not truly the case. We can see the same decision play out at the micro level, too. For example, in performance events such as a sport, deciding to pass a ball now or in a half second from now can each be viable options. Either could have a crucial impact on the game.

The issue is more that we need to consider the impact when ending something. We need to have a sense of what will happen when we drop, close, or move away from our current focus:

  • Will it be there when and where we want it to be?
  • Is it ok to simply drop?
  • Will it take care of itself?
  • Will it be in the way of other things?

We can call the process bookmarking, saving, among other options. It is about taking care when we close a session.


These occur at macro or micro levels.

As an example at the macro level, if I suddenly need to wait for someone or something else to continue a project, I may wish to start another in the meantime. Simply dropping the current project would be problematic. But this is a common occurrence. Instead, we need to consider the return.

In OmniFocus, I can:

  • Set the project on hold (context menu)
  • Consider the review frequency
  • Possibly write a Consider task to revisit it after a period of time.

At a more micro level, I may have to wait while something loads. Jumping to some next thing can easily lead to another jump and then another.

It is useful in such conditions to use the Inbox liberally. So long as I have a regular habit of clearing the Inbox, the Inbox can be an excellent tool for bookmarking. I can:

  • Write whatever tasks I would like to continue.

For example, “check on files after upload.” While the task itself is not a well written task, it does not need to be. It is in the Inbox where it can later be processed. When I do finish what I’ve moved on to, I can return to the Inbox and process it. If the file check could take less than 2 minutes, I can do it. If not, I can expand and adjust the task as would be useful.

At an even more micro level, the performance state, we can no longer use an external tool such as OmniFocus. In such states, I find practice of the work and, perhaps, a practice of meditation to be most helpful. For example, if I am performing a piece of music and I think it would be useful to return to a previous passage, I may consider:

  • Do I remember how the previous passage went?
  • When would I transition there?
  • What effect might it have?

And yet all of these questions are hardly questions. They are more an amalgam of feelings that imbue the moment while also leading the current flow of play. In this sense, waiting is no longer “hard” so much as it is a part of the work itself.

The Power of The Inbox

When used well, the Inbox can be one of the most powerful tools in your productivity toolset. But using it well requires recognizing its delicate nature and taking care of it regularly.

Examples of The Inbox’s Utility

First, let’s consider how the Inbox can be useful.

We can leverage the Inbox when deciding what to do next. Brainstorming, allowing whatever comes to mind, we can add ideas to the Inbox as thoughts appear. The inbox helps us store those ideas, so we don’t have to keep trying to remember what we’ve already thought of. It gives us a place to offload our concerns and interests. We don’t have to worry that we’d forget something we considered.

The Inbox is useful when first sitting down with something we’ve decided to work on. Those moments are ripe with ideas about how things could be better or other things we’d rather do. Jotting down these thoughts helps us avoid distraction. It helps to avoid organizing our way into procrastination. Instead, we offload thoughts so we can better warm up the work.

The Inbox is useful during a session of work. We can add distractions that come to mind, store multiple ideas for the current project, field incoming distractions, and more. Within reason, those ideas will patiently wait for us until we are done with the current work.

And the Inbox helps us when we’re wrapping up a session of work. We can consider what is needed to save things, how we want to return, and more.

The Need for Upkeep

But, without regular cleaning, the Inbox loses vitality. It becomes something we can no longer trust to hold our ideas until they’d be useful. Thoughts grow stale, irrelevant, or get lost when they could have been useful.

Too often, we can let the inbox go, particularly when we are first learning systems of work. We haven’t yet formed that internal sense of its power and how delicately it rides on our care of it. But when we do have this habit of clearing well practiced, we can better feel its power.

To clear an Inbox, the general recommendation is to start with the top item and move down until complete. We need to carefully consider each task we’ve put there. If something can be done in 2 minutes or less, do it. If not, place it where it needs to go so that we feel it will reappear when and where it would be useful

Because if its work, processing the Inbox is often a major point of resistance. Realize that clearing the Inbox takes time. To do it well, consider dedicating a full session of attention working through from beginning to end, until it is completely clear.

Even better, when it is clear, allow your mind to clear, adding more thoughts to the Inbox until no more come to mind. Again process the Inbox. You will be that much further along in having a solid system supporting you, so you can place your mind where you want it with focus and clarity.

Switching Projects Between On Hold and Active

Often we need to juggle our attention between numerous projects. OmniFocus helps to simplify matters of our decision by allowing us to place some projects on hold, and then later activate them. When we set a project on hold, all of its tasks change from being “Available” to “Remaining”.

For the most part, our work perspectives rely on a filter by availability setting of Available or First Available.1 Therefore, when we set a project on hold, its tasks no longer appear in our usual working perspectives.

We can switch between the two states either by:

  • using the contextual menu (accessed by control-click):
Set project On Hold via contextual Menu

Set project On Hold via contextual Menu

  • Through the menu (Menu > Edit > Status > On Hold)
  • or by Inspector:
Set project On Hold via Inspector

Set project On Hold via Inspector

Adding Key Commands

Key commands often make a significant difference in one’s workflow. If you know the key commands for an action, not only do you become much quicker with the program in general, but actions become more easily used, and therefore they become more often used.

As a result, I tend to prefer key commands. However, as there are no key commands assigned, I use Keyboard Maestro to create one. If you are interested in doing so, below are the settings2:

To set a project On Hold:

Set OmniFocus project On Hold settings for Keyboard Maestro

Set OmniFocus project On Hold settings for Keyboard Maestro

To return a project to Active:

Set OmniFocus project to Active settings for Keyboard Maestro

Set OmniFocus project to Active settings for Keyboard Maestro

For extra credit, this one is to drop a project:

Set OmniFocus project to Dropped settings for Keyboard Maestro

Set OmniFocus project to Dropped settings for Keyboard Maestro

Give it a shot. I bet that once you can jump between states just using Option-h and Option-a, you’ll find a subtle, but significant difference in your workflows.

      1. Tasks have several states of availability:

      • First Available – Displays in Next Available task filters
      • Available – Displays in all Available tasks filters
      • Remaining – Displays in all Available and Remaining tasks filters
      • All – Displays in Available, Remaining, and Completed tasks filters
      • Completed – Displays in Completed tasks only filters

  1. For a more thorough explanation of setting up Keyboard Maestro macros for OmniFocus, check out this post.

Kanban and OmniFocus

Lee Garret has put together a neat Kanban type system in OmniFocus using a series of perspectives.  Check out his post here. He first mentioned it in his session at Learn OmniFocus, which you can check out here.

A Kanban system is one in which one establishes a series of nodes for work. Work passes from one node to the next, be that physically or digitally.

The Three Principles of Organizing and its Practice

When we organize, what are we doing?  Do we put things into nice orders?  Make them somehow aesthetically pleasing?

I define organization as:

Organization is the process of clearing and supporting paths for the development of things we find meaningful.

To clear and support paths, there are three components:

  1. Accessibility
  2. Avoidability
  3. Awareness

Accessibility refers to how easily we can get to something when we need or want it.  Ideally, it is instantly accessible. When we are truly skilled at its use, we may barely even know we are using it.  For example, we can consider common words of our primary language as instantly accessible.

Avoidability refers to how easily we can avoid something when we do not need or want it. Ideally, it is invisible.  For example, a coat in the closet during the summer months is generally invisible and quite avoidable.

Awareness refers to how are we are of whether something is supporting us or in the way.  It directly correlates to accessibility and avoidability, respectively. Ideally, we should be instantly aware of whether something is supporting us or not.  As an example, if I want to know when the next bus arrives, if I am unaware that an app exists to tell me that information, that app is, in a sense, not organized.

The reason I bring this up, and the reason I bring up such varied examples, is to demonstrate that these principles exist in all media, including our task systems.  We wish to be aware of a relevant task when and where it is important to be aware of it, and not at other times.

Further, the skill of organization is a practice. Too often, people label themselves as “organized” or “disorganized”. The above set up removes such state-like descriptions and instead makes organization itself a relative thing.  If you live in what others would call messy but it still supports you well where you find things to be meaningful, then you are organized.  If you wish to make things more organized, you need to then consider,

  • How can I be made more aware of something when and where I need to be?
  • How can I make something more accessible/useable?
  • How can I make something more avoidable when I don’t need it?

To practice organization, I could suggest the following:

  • Create a repeating task in OmniFocus. Consider using the Defer Another function set to daily.
  • Title it: Organize one object.
  • Flag it or give it a context in which you would see it daily.
  • Copy and paste the 3 questions I’ve listed above into the note field.

When the task arrives, choose one item nearby that you haven’t used much lately, but is still hanging around–some piece of clutter–and ask the questions.  While the practice does gradually help you organize one piece per day, the practice itself begins to build a certain skill that you can use throughout your days.

For more detail and practice with organizing and its principles, consider Workflow Mastery: Building from the Basics.

Handling Deadlines and Multiple Projects – with OmniFocus and MindNode


Juggling multiple deadlines, knowing what to start and when, and knowing what we will be able to take on a few months from now is not a simple matter. Each project we take on will likely last an unclear amount of time, and we’ll have other responsibilities to take care of in the meantime.

In this post, I’ll describe how I’ve been planning and setting up several long term projects using a combination of MindNode and OmniFocus.  In the course of developing this post, I also created a video version more streamlined to the exercise of planning the start of projects. The video is posted above.

The end goal is the same as always: a centralized, simple list that I trust to present the things I want to do during the day. I want to see something like the following:


The core concept of this post is simple:




Plan the beginning of your projects.




However, how I present things may still fall under advanced use.

You’ll need to have some functioning task system, and a system of setting project On Hold and Active.  Using OmniFocus, I’ve developed the Land & Sea project (link 1, link 2, link 3.  A more detailed, though earlier version, is described in Creating Flow with OmniFocus, page 706) to this end. It is a complex table-of-contents-like project that helps me navigate several of my ongoing projects.

In addition, you will need a sense of what I call The Workflow Fundamentals. In short, these are the practices of:

  1. Deciding on a piece of work,
  2. Sitting with that work, and
  3. Then doing so regularly.

These sound simple, but as anyone with a tendency to procrastinate can attest to, they are not. (For a full study, I refer you to  Zen & The Art of Work).

I’ll also use both OmniFocus (for task management) and MindNode (for outlining).

Calm Juggling

The video displays a set of the projects that I have been working on over the past several months or so.

Throughout all of these, I’m also seeing my clients, managing their therapy and medications, practicing piano, meeting family obligations, doing the dishes, taking out the garbage, and even reading, helping the kids with their homework, or playing video games in the evenings.

That sounds overwhelming.  And, if I were to have some omnisience of how my work days would turn out, and then and attempt to work from this blueprint, I bet I would fail. This thing is overwhelming to look at.

It would be impossible to work from here. But this is how we often try to plan. We think we should know all the steps before doing something. But this approach can instead be paralyzing.

Creativity is an act of discovering something as we make it.  The act of choosing which projects to take on and when can itself be creative.

And while I do have days of stress, they are not from a sense of inability, so much as they are about my dealing with the arrows reality has decided to sling in my direction. I maintain focus, clarity, and often calm.

I never feel overwhelmed because I know how to adjust the throttle and still meet obligations. When I have that sense of guidance, work is no longer an inevitable chore.  It is something I decide to take on at the pace I believe would work well for me. I can plan, and I can always change my plans.

A Set of Upcoming Deadlines

Recently, I’ve been in the midst of preparing several public talks. The presentations themselves are meant to be anywhere from 1-3 hours each. Essentially, each talk is a performance.  I need to put together a set of ideas, some of which I’ve formed in advance, many of which I haven’t. Then I need to practice them, so I can simultaneously stand in front of a bunch of people, say something that is hopefully meaningful to them, and hopefully not fall on my face.  And, since they are performances, I can’t just have them ready months in advance. I also need to practice them in the days leading up to the presentation.

My general system of work is to start a project early, preferably as soon as its assigned, and then sit with it daily. However, this is not possible for 6-8 projects simultaneously. Using the Land & Sea Project I limit myself to doing about 3 projects simultaneously. Meanwhile, the odds and ends of other projects find their way into my File & Flow perspective or in Communications (old link, but still relevant). The 3 Land & Sea projects also need to include work that is not about speaking gigs. Besides, I don’t really want to work on several talks simultaneously, so I can better concentrate on them individually.

Planning in MindNode

Starting a few months ago, I began a sketch of the talks that were on my mind:

Capto_Capture 2016-12-01_06-21-48_AM.png

As I planned, I used MindNode’s ability to create tasks (Shift-Command-t) to list the presentations and some of their dates. Later, I added  tasks about planning itself to the top to keep them separate from the rest of the tasks:

Using MindNode’s task system, as opposed to that in OmniFocus, allowed me to stay within MindNode itself. However, I still use OmniFocus as my central hub of task management.

While I was planning, I realized that I wanted to spend several sessions doing so. Therefore, as I was in this initial planning phase, I added the task to continue planning in MindNode to OmniFocus, like so:

That way, I could spend a session planning, then mark the task complete, and it would show up again the next day.  I deleted the task when I was done outlining.

As I continued planning, some tasks would easily be completed and never find their way into OmniFocus.  These would mainly be about planning, like those listed above. Other tasks, though, would be better suited to my overall system, like communication tasks or really anything that needed to be called out outside of the planning process (examples circled below):

Capto_Capture 2017-02-05_06-29-27_AM.png

These tasks that do not refer to planning within MindNode itself are better suited to OmniFocus. While there is an export option in MindNode to send tasks to OmniFocus, I prefer to make the transfers manually. That way, I can distinguish between those that are embedded in MindNode and those that I want in OmniFocus.

When transferring a task, instead of marking the task as completed, I use the strikethrough option (Option-Command-u):

Capto_Capture 2017-02-05_06-37-14_AM.png

to indicate that they’d been transferred.  That way, I could leave them in MindNode as I continued planning and knew what had been transferred.

I eventually came up with a series of potential start dates for preparations, usually at least a few weeks or a month beforehand:

Capto_Capture 2017-02-05_06-40-47_AM.png

Transfer to OmniFocus

When done, I then transferred dates of when I wanted to start each preparation to the Land & Sea project.  Here is a screenshot of a more recent Land & Sea project:

The top section, labeled “Navigation”, is relatively new:

Essentially, it is a set of reminders to make adjustments to the Land & Sea projects based on my plans. The group is set to parallel:

Plan in Action

In the end, I maintain a simple presentation of tasks in my day to day:

Capto_Capture 2017-02-04_09-12-30_AM.png

When the date for starting preparations arrives, that particular task appears in the simple list of the Dashboard (link 1, link 2) shown above. I can then make arrangements, removing something else from being active in Land & Sea and replacing it with what I want to begin.  Meanwhile, if I finish preparations for something early, I can always move something from inactive to active earlier.

I can also leverage the Forecast Perspective to keep my eye on the horizon. I can:

  • Select the Land & Sea project
  • Focus with Shift-Command-F, and
  • Open the Forecast Perspective (Command-4), with deferred items shown

to present the upcoming month without interference from the rest of my project library:

Capto_Capture 2017-02-04_08-23-12_AM.png

Certainly there are other ways to plan ahead. But this has been nice for me. Once I had it set up, I really could just run on autopilot, sitting with the work in my daily list of tasks. In general, using the start-early/sit-daily method of work I described above, I tend to be done with projects well in advance of any due dates.  I can always re-add a project in the days approaching the talk to get the material fresh in mind for the talk itself.

I never force myself to work. The point of will is being with the work.