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Update to Zen & The Art of Work

Zen & The Art of Work received an update over the weekend. Module 11 on Mastery is now more concise and, I hope, better conveys its core message. The audiobook has also been updated.

If you’ve already purchased Zen & The Art of Work, the new version is available for you to stream or download via your Gumroad purchase account.

Two Ways to Break Work Down

Work can feel overwhelming. What to do next is not often clear. One way of handling this overwhelm is to “break it down” into smaller parts.

But how far is useful? If we continue to write many tasks that feel unnecessary, we only create busy work or procrastinate.

There are two measures to consider when breaking down tasks:

1 – For simple work, break to the Point of Confidence

2 – For mastery, break to the Fundamentals

When doing simple work, I find it is useful to break something down to the point of confidence. For example, I may break down “Clean home” into “Clean kitchen” and “Tidy living room”. While the latter two don’t fully convey cleaning the entire home, the original task was far too broad. The latter make more sense to me. I know what to do to clean the kitchen or tidy the living room. Someone else without the practice may wish to break things down farther, e.g. “Clean dishes”, “Wipe counters”, etc.

But, when I’m doing a work I intend to master, that’s a different story. Doing only things that I am confident in is a great way to stall. There are quite a few musicians who noodle away at their instrument without making much headway in their skills simply by doing what they already know. While there is much to be praised about review, there are also paths of unknown that need traversing.

In the case of mastery, it is useful to break things down to the point of fundamentals. In other words, we need to break the work into its most basic components, the most simple, even atomic, parts that cannot be broken down any further. Each of those parts, separately and together, can be played with and worked over until they are individually effortless.

As there are two points of measure, it is therefore very important that before beginning work, we consider if we are aiming for mastery. Mastery is a path that takes dedicated and regular time and effort. We are all limited in our time and attention.

On Time Blocking

What is time blocking?

Time blocking is the act of scheduling sessions of work on a calendar. By deliberately assigning work time on a calendar, we automatically acknowledge the immutable resource of time.

Several productivity writers tout the strengths of time blocking including Mike Vardy at Lifehack, Cal Newport of Deep Work fame, Gwen Moran at Fast Company, Francis Wade, and others. A number of task management apps work by time blocking, sometimes even automatically scheduling your days such as SkedPal. The productivity method known as the Pomodoro Technique also presents the idea in its own form.

Some practitioners schedule all planned work throughout the day, completely filling the calendar. Every minute is assigned a job. Flexibility and buffered time are also a part of the planning process. Importantly, time to do the planning is itself honored.

With practice, one may find benefit to dedicating times of the week to certain types of work. For example, specific times for intensive creative work may do better earlier the day. A regular time to review our systems once a week, as prescribed by GTD, can also beneficial. We can also schedule batches of small routine tasks among other possibilities.

Task Management vs Time Blocking

Task lists may appear to conflict with time blocking. Newport’s point has validity, though I am not entirely in agreement. Certainly, there are those who place far too much on their task lists, throwing any form of realistic task maintenance to the wind. In reality, I think we argue for the same point, which is to recognize that one of the vital resources of any work is time.

Time blocking may seem to go against a central GTD tenet, which is to use the calendar only for “hard landscape” items such as meetings. However, this is not necessarily the case. A nice response by GTD coach Janet Riley can be found here. As always, GTD is about creating a system you genuinely trust to hold what you do not want to be on your mind currently and present it when you do, however you decide to make that system.

Sessions are the Primary Unit of Work

Most important in the process is the acknowledgment of the session as the unit of work, not the task.


A Session is the union of an intention with its resources of time, attention, and space.

A task is only a reminder of the intention. At best, it is an invitation to the session.

Personal Experience

Personally, I don’t always time block.

In fact, I only rarely do in the occasions that I feel scattered, somehow over-committed, that I am facing a particularly empty day, or that I am not truly dedicating myself to a project well enough. In general, I prefer to maintain a small, well-curated list of active projects that I only promise myself to touch upon daily. If something else comes up, like a weekly review or a monthly billing project, I might push one of the projects off to the next day. Or not–depending on my sense of the day.

I decide the time I spend of a session, whether that ends up being 5 minutes or 2 hours, as a compromise between  my internal and external views of the work. Internal refers to how I see the work while I am in the session. External refers to my time of planning the day. I find that relying too much on one or the other to be problematic.

Particularly because I view the internal view of a session as being equally important, I tend to shy away from scheduling too much.  I value the habit of visiting work with regularity to have at least as great an importance as the time involved.

More often, I will:

  • Examine my already well curated day’s list
  • Review the calendar for what hard landscape items exist
  • Choose a task in the current window of time
  • Acknowledge a time at which I would like to consider closing the session
  • Consider setting an alert
  • Begin the session.

However, the above description doesn’t embody the fluid nature of the process.

For a full examination see also Zen and The Art of Work – Modules 5 and 13.

Considerations & Cautions

While I time block a full day only sparingly, that is not because I think the practice is without merit. In fact, I think it can be quite powerful.

However, because of its power, it is probably not something I would recommend pushing too hard until one has found a certain mastery in productivity work. Far too often, I have found others who first try to get on top of their work by time blocking. It is similar to learning to weight lift by going for the heaviest weights first. Individuals doing so often fail and end up berating themselves along the way, creating further struggles of procrastination and feelings of helplessness.

I do believe that time blocking is a deceptively advanced technique. To do it well requires a history of habit development in time and task management. Before those muscles have been formed, scheduling to this degree, one needs to know how to buffer and adjust throughout the day, have a sense of what exceptions work and what do not, have a practice acknowledging interruptions from the self and the world, among other practices.

In learning to do well with work, one is adjusting their identity.  Going from someone who feels hopeless in getting anything done to one who feels like they can decide on what to do and how to take steps forward is not a small feat.  I wonder if time blocking rests, at least to some degree, on that identity of being productive.

In Practice

Should you choose to time block, consider building buffers into your system and recognize that creative work will take an unclear amount of time. As creative work is discovered in the act of its creation, both the steps and the end goal are, at best, blurry until reaching the end. In this way, the time blocks are not useful as something with which to “beat the clock.”

Instead, consider blocks of time as single sessions of work to dedicate to a project. That way, you recognize that you may not be done with the work at the end of the dedicated time, and that you may find it useful to continue another session later, perhaps the next day or later in the week. Of course, this also depends on your habit of scheduling projects well ahead of any deadlines.

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.

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A Guiding Principle of Task Management

A Guiding Principle of Task Management

A guiding principle of any solid task management solution is a clear mind. For example, the popular productivity solution Getting Things Done focuses on what it would take to honestly clear the mind, and then designing our environments and systems accordingly.

It may seem odd to consider a clear mind as a centerpiece in building a working system. In many ways, we would hope such a state to be more of a desired end result than as an approach.

But a solid organizational system develops in an iterative acknowledgement and addressing of the things that are on the mind. By regularly placing those things that cannot be done now in places where we honestly and truly believe they may be done, we clear the mind of present concerns while uniquely creating and shaping the useful systems that surround us.

That system, though, must be trusted. So let us take a moment to examine what we mean by a trusted system.

The Importance of a Trusted System

Trust is the foundation upon which we can build systems to develop and maintain whatever we find as meaningful. A trusted system allows us to maintain that sense without our direct attention.

Defining trust:

Trust is a belief, developed over time, that something will continue behaving as it has in the past, such that it may be relied upon.

The theory is:

If we can truly and honestly trust something to be when and where it is needed, it will be off of the mind.

In other words, we use an honestly clear mind as the guiding principle of knowing that our environments can be trusted to help us continue developing whatever we find as meaningful.

We build our systems so that we can trust that they will optimally remind us of what we want to be reminded of, only at those times where we would like to be reminded. To build these systems, we need to know what it would take of our environments and ourselves to honestly trust them.

Trust In Self

Further, this process becomes more than about our surroundings. As we address what is on our mind with whatever honesty we can muster, we also build a trust in our selves. As our skills in addressing what is meaningful to us develop, so does a trust in our abilities. We learn what we can do, what we cannot do, what we can improve, and, sometimes, how we can improve. Another term for this is “confidence”:

Confidence is a trust in our ability. It is a developed sense of our own capacity to meaningfully decide and act, such that it may be relied upon.

The above is an adaption from Workflow Mastery: Building from the Basics

Making Decisions

Making Decisions

Impossibilities in Work

Work can be stressful. Demands, obligations, and the need to make regular decisions can assault us from multiple directions. To make it worse, many of these demands conflict with each other or are impossible to do in the time frames given.

While we can hope that our work world would change for the better on its own, that wish rarely finds reality. We can also decide to work for the idea of future relief: leaving at the end of the workday, getting a massage at the end of the week, or going on vacation sometime in the coming months. But how often, when we return, does that second or third email throw us back into the turmoil as if we’d never been gone in the first place?

Task Systems Are Not Enough

Task management systems can be very helpful. Learning how to arrange work, reduce clutter, and create useful tasks can help us make decisions and work through the things that need to be done.

But they are often not enough. Knowing what we can do, let alone what we can do well, is often unclear until we’ve tried. We can joke that just writing a task doesn’t do the work for us. And, when we see how little we can get done or that there were other paths we could have tried, we might find regret and overwhelm.

The issue is not that current task systems are not good. They are, in fact, quite excellent when used well. However, their approach is entirely “outside-in”. They leave a massive blindspot where our experience sits. How we are during work and how we experience work itself is often lost.

Most tasks take longer than we think: suddenly we realize that some call needs to happen before we start writing, another idea someone had now needs adding, or that we could have gathered our thoughts better before a meeting we now find ourselves in. Decisions and the work itself are often clarified as we get to them, despite our best preparations.

We need to add an “inside-out” approach to help give us the edge, to help us gather a real sense of how our work forms, and to fully realize the limits of time and attention. When we have that experience, we can address our work so that we maintain focus to do what we choose to and do it well, even when too much comes our way.

An Exercise in Decision

As the simplest example of what I mean by an inside-approach, consider trying the following exercise. At some point today:

  1. Stop what you are doing, so long as it is not irresponsible or reckless to do so.
  2. Then pause.
  3. Actively rest your mind on the decision about what you’d like to do next.
  4. Vital to this process is that you wait and not act while you are considering what to do next.

During this time, more than likely, many ideas will come to mind. Things you might want to do, are worried about, things you feel you have to do, or otherwise will appear.

Let these ideas and feelings come to mind. You can have a piece of paper nearby to jot some of them down or you can close your eyes while doing this.

As your mind wanders, let those thoughts fade off and return your mind to the decision until no further thoughts appear.

5. Wait until no new ideas about what to do next come to mind. In other words, when your ideas and feelings start to repeat, fade out, or just sit there, even as you continue to pause, you are ready.

6. At that point, you can make a settled decision.

I’m willing to bet that whatever it is you choose to do, be that a project or checking email, contacting someone about an important matter or even just playing a game if that’s what you decide to do, will be given greater focus and even a greater sense of meaning.

Importantly, you may also notice that this process takes time. It may not be long. Sometimes a few moments will do. But when you have that vital, direct sense of this very useful process taking the time it takes, you will be much more inclined and able to say, “Give me a moment to think here” in the many ways that can be phrased so you can give your thoughts the time they need to form.

This is even more important when you are pressured such as when someone tells you do these 5 things and you already have 7 things to do on your mind.

Much of our work worlds nowadays assault this sort of decision making. We can blame technology, we can blame our work environments, and we can blame ourselves. Regardless, the responsibility to give our thoughts the time needed to form is our own.

The Courage to Pause

The Courage to Pause

We can only act here and now.

Of course, this seems obvious, but it is not. In fact, there are reasons to hide from the present moment, and we can easily do so without realizing it.

Acting from the present means directly facing the real limits of time and attention. We would realize that whatever we choose to do now will take every other choice off the table, at least for now. There are many feelings that come with that knowledge.

But when we do act with full presence, we face the limits of time and attention with strength. The risks needed, the mourning of lost possibilities, and the acknowledging of fears in paths taken — all factor in to a solid decision.

It is not easy to face the current moment. But the act of doing so is simple — that is to pause.

Pausing returns us to the present. When we pause, our current world of worries and want, our thoughts and feelings, all have time to settle in conscious awareness.

It takes courage to pause. But when we do, our decisions gain strength. We find footing, courage, and adaptability to move forward.

Welcome to Zen & The Art of Work

Welcome to Zen & The Art of Work

Zen & The Art of Work is about how we can build our goals and the paths there, throughout life’s chaos. Visit this blog periodically to learn about how we can better build our dreams, with greater focus, creativity, and less stress.

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