Some of us have a “wandering mind”.

Perhaps you are creative, struggle with ADHD or anxiety, or simply have a driving curiosity. In whatever manner by which you have one, a wandering mind can often make it difficult to find focus.

However, one advantage of a wandering mind is that it can sometimes revel in a state of Flow — a hyper-focused world where everything else slips away. The inner critic is quieter, if not silent. Ideas flow and merge. A sense of direction and the possibility of getting somewhere energizes.

But while creativity and the thrill of engagement blooms, there is the Dark Side of Flow to consider. When not managed well, its power can leave a wake of trouble, be that lost responsibilities or even hurt relationships.

Managing can seem impossible.

Flow’s enjoyability blissfully allows you to lose sight of the rest of the world. But, there are other things to do. There are responsibilities. Even things you’d enjoy can get lost in the shuffle. It can be very easy to forget that Flow needs time.

One thing you might try is to set up reminders. But doing so without thought makes them nearly invisible, barely heard. Since they are not part of the hyper-focused world you are in, it’s like they don’t exist.

Another solution is to get other people to help. Either offered by a well-meaning other or requested, the idea is to have someone shake you out of your trance to remind you to do the laundry, take out the garbage, write a report, or otherwise.

Unfortunately, that person doesn’t know where your mind is. Whenever they tap your shoulder, it’s never the right time. Those creative moments can be rare and precious. So you might respond with a polite thank you, often tinged with subtle resentment. Or you might just yell, “Not now!”

To make matters worse, you might even feel guilty because you just shut down this person who was offering help.

There are, however, better ways to use reminders to alert yourself, ways that might just gain your attention.

If you hear a reminder that is unique to the moment, meaningful, easy to engage, and respectful of where you are now, it is much more likely that you will want to act on it. You will be much less likely to disrupt Flow, and instead guide it.

Creating potent reminders is a practice of respecting Future You. Doing so also gives Present You a more guilt-free engagement of whatever you are doing now.

What’s more, because you are taking control, you stop sowing the seeds of a love-hate duality with those you could otherwise enjoy company. Your conversations no longer center on “When are you going to do X?” with the inevitable response, “Later!”. Instead, room forms for conversations about mutual interests, the day-to-day, and future projects.

If you are interested in learning exercises to create more useful reminders, consider joining the list for Waves of Focus — Guiding the Wandering Mind, a live cohort-based class planned for Fall 2021.

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.

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:

Prerequisites

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 isoverwhelming 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 & Flowperspective 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:

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):

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):

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:

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:

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:

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.

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 our 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

Kourosh Dini, MD is a psychoanalyst, time and task management expert, and the author of:

• Zen & The Art of Work: Exercises for Mastery
• Workflow Mastery: Building from the Basics
• Creating Flow with OmniFocus: Mastering Productivity

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.

Kourosh Dini, MD is a psychoanalyst, productivity expert, and the author of Zen & The Art of Work, Workflow Mastery, and Creating Flow with OmniFocus.

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.