GTD, Management Thinking, Self Improvement

6 Reasons Planning Is a Pain (and Why You Should Do It Anyway)

qtq80-WsNgkaSmart, capable people often struggle with one crucial aspect of knowledge work: planning. In my experience, clients resist planning for a number of reasons. Here are some of the most common.

Planning causes mental pain, at least at first. Planning is taxing work. If you haven’t done it recently or it’s not a habit, it will literally cause pain when you do it. My university students helped me define this pain; it is the feeling of frustration. “It’s too hard.” “I’m just not good at this.” So, we give up too easily, avoiding the frustration of learning how to plan and developing the habit of planning.

Planning takes time. On average, your weekly planning will take 45 minutes or so. That’s for a routine week. If your upcoming week is challenging, planning may take twice that long. Daily planning will take 10-15 minutes. As with many activities, it feels easier to just jump in and start work. Doing so makes us feel that we are, at least, making progress. So we skip planning and just get started.

Planning is deep work. Some people think that planning is merely running over their to-do list. But real planning is the difficult exercise of estimating how long tasks will take and a thoughtful look at our tasks versus our constraints. It forces us to clearly define our commitments and deliverables. Most of us prefer to avoid this deep work, so we substitute a shallow, watered down version. We leave our commitments murky and don’t clarify through planning.

Planning forces us to say “No”. We don’t like to say no to others. Good planning shows conflicting commitments and when our capacity is full. Thus, planning forces us to make choices that likely result in difficult conversations. This brings us face to face with our priorities, which may not be clear. It is much easier, in the short run, to play hero and worry about the consequences later, so we don’t plan.

Planning shows hard truths. When you plan, you realize your limitations and understand your constraints. This is much more challenging than just believing everything will work out. Over time, planning also shows you how long it actually takes to get your tasks accomplished. This can challenge your mental image of how good you are at some of your tasks. These challenges are uncomfortable; we avoid planning so we don’t have to face them.

Planning is inexact. Even the most experienced planners and project managers cannot predict the future. Things happen. Key resources take a sick day. A supplier’s truck breaks down. In addition, we are predictably bad estimators, typically underestimating both the time it takes to do something and how much discretionary time we will have in a given day or week. Our plans don’t work out, so we abandon planning.

So, we resist planning because it is painful, time-consuming deep work, that doesn’t work perfectly and forces us to confront an uncomfortable reality. But I would like to show two essential parameters that planning produces: The first is time boxes that show us how much time we can allocate to any given task. The second is milestones, which show where we should be on a multi-step project. Clarity on these two parameters is our responsibility in managing our schedule and tasks.

Time boxes force us to deliver even when the level of quality is unclear. We can be perfectionists and let deadlines slip chasing perfection. Remember that the quality of knowledge work is notoriously difficult to define. Challenge yourself to work hard for the duration, but, when the time is up, ship the result. It is probably at least good enough. Time boxes help give us the courage to “just ship it” on the deadline.

But, even if it is not good enough, you probably don’t know how to fix it. My experience as a writer shows this challenge. I invariably think part X is bad while part Y is good. However, my reviewers and editors think the opposite. So, rather than continuing to perfect part X, I should have been working on part Y. The same holds true for much of our work: presentations, reports, and communication. The parts we think need additional work are actually OK, but we overlook parts that need shoring up. So, instead of exceeding our time boxes and blowing our schedule by chasing our view of perfection, we should set shorter time boxes and use the additional time to get feedback on what needs attention.

In addition, using time boxes gives good historical data on how long a task actually takes. Working on a deliverable in short spurts is inefficient and makes it difficult to tell how much work we actually did. We need to know how long the task took last time in order to guess better how long it will take this time. Disciplined work during time boxes shows us that.

Milestones are advance warning signs that a project may not turn out well. Milestones give us time to renegotiate our commitments while our stakeholders still have time to adjust. In my experience as a project manager, people are usually reasonable when they know of a problem in advance. They are less reasonable when they find out today that we don’t have something they expected to get yesterday. Some of our work is speculative; we guess, in advance, how long a task will take. Sometimes those guesses are wrong. Maybe our stakeholders can do without a piece of the work. Maybe we misunderstood their deadline. Maybe they’re happier with a blue one on time than a green one that is late. But, we only find out by having the conversation. Milestones help us do that earlier.

Planning is challenging and can be painful. But, good planning produces time boxes and milestones. These parameters help us face reality, rather than living in an imaginary, but happy, world of false bravado and superheros who can overcome any constraint. They parameters help us keep our time under control and give us the best chance to make our stakeholders happy. Planning is imperfect, but, when it comes to executing our work, an imperfect view of reality beats a 20/20 view of a fantasy every time. So, overcome the pain and challenges and plan your work.

Question: What is your biggest pain point when keeping on track with your daily and weekly planning sessions? How much does it interfere with creating the habit?

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GTD “trusted” system

In a previous post, I tried to relate the GTD (Getting Things Done, David Allen) reasoning for developing and using a trusted system for storing information and tasks, rather than simply trying to remember things.

A few core ideas and components define a GTD trusted system:

The inbox – there is a single location or entry point for the system. Only one.  Ever. This reinforces the habit of using the system. Further, the inbox should be readily accessible so that when information or an interruption occurs, a note can be put in the inbox quickly, and collected and stored there for later processing. Then you can get back to productive, planned work. Anything, in any form, can go into the inbox. Finally, it is important that you alone control what goes into the inbox, because if others can put things directly into your inbox, it gets cluttered. If it gets too cluttered with junk, it gets difficult to process. If it is too difficult to process, you’ll let stuff collect up – congratulations, you’ve officially fallen off the GTD wagon. This fact alone makes your email inbox a lousy GTD inbox. I’ll cover tips on incorporating email in a later post. Remember – a single, private, inbox that is easily accessible – put everything there.

Processing mentality – process the inbox every few hours, or when there is a natural break in work. There are only three permissible actions: do it, delay it, or delete it. If it can be done (or filed for reference) quickly enough to not break the flow of processing, say 30 seconds, then go ahead and knock it out. If it will take longer to do, then delay it, possibly in a task scheduler or suspension list (more on this in a later post). If it is no longer relevant, just delete it. Remember – decide what it is and get it out of the inbox.

Organized storage – the storage system must be organized so you can find things. What does this organization look like? The answer to this question is not obvious in an age where search has overtaken up-front filing. “Pile and search” is a reasonable choice in the age of Google. For me, search is a valuable tool, but has a complication. I use similar terminology in lots of different ways. If I search my 4500 notes for the word “productivity”, I get back a few hundred notes. This is not particularly helpful.

On the other hand, a hierarchical filing system (such as folders in Outlook) has not proven useful for me. The problem with hierarchical storage is that each item stored can only be about one thing. This constraint means that I am limited on how to find things in the system and have to work too hard to find the “right” place to put things.

I have worked on this for a while and have refined a tag-based organization/filing system that I found on the web. I’ll post details on this topic later, but for a preview, go to The Secret Weapon. The site has a 7-minute overview video. Remember – organization is a key to trusting your system.


  • A single, private, readily-accessible inbox
  • Process often and process to empty
  • Organize your storage so you’ll trust it

GTD has been around for a while and has evolved over time. If you’re interested in more detail, here’s a link I also recommend the book; it is thorough and concise.

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“Getting Things Done” as a productivity tool

I’m constantly working on my personal productivity. It’s an ongoing battle with myself, my toolkit, and the urgent but not important attempts to steal my attention away from important work. This post is the first in a series in which I’ll describe some of the ideas that have helped me; perhaps you can learn from my experience.

David Allen’s Getting Things Done (“GTD”, Amazon books), is a core component of my approach to managing tasks, goals, roles, and vision. I have a lot to say on that broader topic, but I’ll start with the basics of GTD. David Allen talks some about it here (about 22 minutes of video).

 “Your head is for having ideas, not for holding them.” – David Allen

GTD’s central premise is that the human brain is terrible at a specific kind of remembering, namely supplying information at the time we need it. As an example, say your spouse calls and asks you to pick up milk on the way home from work. You are happy to do so, but you’re not leaving for a few hours, so you have to remember to do it. You want your brain to supply the information when you need it – ideally just before you drive past the store. As you may have experienced, this is an unreliable mechanism (i.e. you often forget the milk).

According to GTD, your brain has only one means to “remember” a task – think about it constantly, keeping it in short-term memory. In this sense, your brain is constantly using resources, saying “Did we get the milk?” and “Don’t forget the milk.” GTD asserts that this kind of remembering, in addition to being unreliable, is a background buzz that consistently distracts our attention from the productive tasks we need to be doing. Neuroscience and our own experience show that we do our best work when our attention is completely focused on our task (don’t even start with me on “multitasking”, humans simply cannot do it for meaningful work – look for a specific post later). So, how can we get that brainpower and focus back? GTD’s solution is to get what we need to remember out of our brains and into a trusted system.

The idea of a trusted system is: once your brain recognizes that you will be able to find the information or task in the system, it will stop reminding you of upcoming tasks and other information. Your brain will eventually start thinking: “I don’t need to remember the information or task. I just need to remember how to use the system where the information or task is stored.” In this sense, you experience fewer internal interruptions and can utilize that brain power for greater productivity. Advocates of GTD use the term “mind like water” to describe the feeling of freeing up this part of your brainpower. In an upcoming post, I’ll describe the kind of trusted system GTD recommends.

Personally, I find that I no longer worry much about where information is and that I don’t forget as much as I used to. To me, this is indeed a relief. You may decide to use some of these thoughts, or use some others, but as a knowledge worker (see the homepage), your attention and brainpower is your most important asset. Don’t let it be wasted.

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Time According to Drucker’s Watch
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GTD, Productivity

Great quote on managing your life

“If you can’t manage the details of your life, whatever level you’re at is the highest level you’re ever going to go.”
– Jeff Heilman, from an interview with Mike Williams of DavidAllenCo (GTD)

The interview is a little long at 45+ minutes, but I think it’s worth it.