Goals III: Planning

Everyone has dreams about what they want to do in the future. Write a novel, learn a new language or make a trip around the world. Yet it can be hard to motivate yourself to work on realizing these dreams on a consistent basis. How can we align our daily activities with our long term goals? I address this question with a three part series on goals. In the third part we look at the actual process of planning.

Introduction

Thinking and Acting

Say you get in your car in the morning to drive to work. You get behind the wheel and think about the first point you need to get to. This first point, let us call it A, is halfway between where you are now and your work. Then you think of the second point which is halfway in between where you are now and point A. Let us call this point B. If you follow this line of reasoning, the distance between you and your work can be divided in half an infinite number of times. You will be forever reasoning in your car about what the first point to drive to should be: A, B, C, D, etc …, without actually even starting the engine. This is the first problematic way many people treat their dreams: thinking, but not acting.

The next day in your car, you take a different approach. You get behind the wheel and just randomly start driving in some direction without even thinking about where your work’s office actually is. You just drive. After driving around for a long time, the office is nowhere in sight. You keep driving infinitely without actually getting anywhere. This is the second problematic way in which many people treat their dreams: acting, but not thinking.

The Planning Spectrum

These different ways of approaching a goal are not as mutually exclusive as they seem. Each approach, in a less extreme form, can lead to success. They are on a spectrum. Overplanning is on one side of this spectrum and underplanning on the other. Depending on the situation, people lean more towards either of these extremes based on how they dealt with similar situations in the past: the familiarity of the goal, which changes over time. Consider that if you are driving to a new place for the first time, you probably plan it to some extent. Contrast this with your daily trip to work, which you likely do without any planning.

This goes to three core insights:

  1. Going too far in either direction, underplanning or overplanning, will get you nowhere.
  2. Planning for goals that are concrete, or that you know how to approach already, is far easier than planning for vague or novel goals.
  3. Planning challenges differ a lot from one person to the other, and even for the same person at different times for different tasks.

Contrary to what is sometimes suggested: there is no one right way to plan that works for everyone, every time for every situation. However, what you should learn to do is continuously adapt and improve your own planning process. Not only should a plan itself adapt to changing circumstances, your approach to planning should adapt to your changing self.

Rather than present a rigid planning method, I am going to provide you with building blocks that you can use to enhance your own planning process. You likely need to apply different parts of this toolbox to different challenges at different times. I can show you helpful blocks, but you will need to put them together. Ready?

Macro Planning

The Anti-Climax

When you work towards a goal for a very long time, and finally reach it, it can feel like an anti-climax. The reason for this feeling is that, from a cognitive perspective, you spend most of your time not reaching your goal. This is followed by a very short time in which you will have actually reached it, before you quickly move on to the next goal. Going through several cycles like this can easily deplete your energy to start any large endeavor. This is why large projects can often feel so overwhelming. The reason that most people never get to writing a book or learning a language is that these cognitively feel like ‘big’ things: large commitments followed by a short-lived reward. Unfortunately, this thinking prevents us from ever actually starting.

To get through this impasse, the divide and conquer approach is often advocated. The idea is to break down a goal into smaller subgoals in a top-down fashion. However, though useful, it is not the right first step. The problem with this approach is that it forces you to consider the scope of the entire goal as a single large project. This perspective sucks you into spending a lot of time just planning your project. You never actually get to work on the project itself: the meat, the content, the challenge. This way goal setting counter-intuitively leads to inertia.

Regular Commitment

A good first step is to commit a regular amount of time to a goal and then to start working on it. Initially this commitment could be just half an hour a day, or a handful of hours in a weekend. It is important that you write this commitment down, stick to it, and check it off as you go. This system forces you to keep track of your time, restricts the goal from taking over your life, yet allows you to reap an immediate reward from putting in time and effort.

Simply taking some first small steps in your regular time allotment for the goal will help you get a better gauge on what challenges lie ahead, how much time they will take to overcome and what other resources you may need. Once you get a feeling for this, take a moment to write down accurately what criteria need to be met for you to consider your goal reached. This has the important dual function to provide both a relative sense of progress and absolute closure.

It is only after this that the divide and conquer approach comes in. However, instead of breaking up big goals into smaller ones top-down, I recommend doing this bottom-up. Just plan out the next two or three things you need to do, place it in the bigger picture of your goal, and resist the urge to make a complete plan.

For example: if you want to write a book, commit to writing a smaller part. This could be as little as a half page outline, or as much as a draft chapter. It is important to define this chunk in a way that you feel you can complete within a reasonable amount of time. After completing this you will have a clearer idea about follow-up steps.

Baby Steps to Giant Leaps

If you are just starting out with something, a new project, it is often best to start small: an initial milestone that you can complete in one or two weeks. This first milestone has the important purpose to get you started: to break through any inertia, and move you one step closer to your goal.

As you put in more time, it also becomes more important to review the completion criteria for your goal and plan the next tasks in alignment with it, or even to alter your definition of done. Having a larger overall plan becomes more important only as your project steadily progresses: as you move closer towards your goal. If you are not yet comfortable with large goals that span months to complete: start with smaller, less ambitious goals. Completing smaller goals will move you forward and provides the foundation for tackling larger goals later on.

Thinking about your goals in terms of days, weeks or months, is macro planning. This is what we have just discussed. It is mostly concerned with filling in the bigger picture in manageable steps as you go. Managing your time during the day is micro planning, and we will get to that next, but not before we define deep and shallow work.

Deep versus Shallow

The Distracted Mind

I had a co-worker once who was continuously distracted by anything that required attention ‘now’. He could not prioritize his tasks and ended up constantly ‘putting out fires’. This person was convinced he could multi-task effectively. In meetings he would often work on his laptop, be in an unrelated phone call simultaneously, while also half participating in the discussion. Had he taken the effort to just add some structure and prioritize his tasks, his productivity would have soared. Instead he was now taking a day to produce less than half a day of effective output.

People who multi-task exclusively perform shallow tasks. These tasks are not cognitively demanding and commonly logistic in nature, for example: responding to e-mails, setting up meetings, and making phone calls. However, when we regard larger goals, such shallow tasks constitute only a very small portion of what needs to be done. Instead these goals require large amounts of deep work: tasks performed in a distraction-free state of concentration that requires significant cognitive effort. For example: writing an article, practicing an instrument, or solving a complex puzzle.

Deep work is the ability to focus without distraction on a cognitively demanding task. It’s a skill that allows you to quickly master complicated information and produce better results in less time. Deep work will make you better at what you do and provide the sense of true fulfillment that comes from craftsmanship.Cal Newport
Single-Tasking

Performing shallow tasks does not actually move you much towards your goal. Doing them exclusively is a form of structured procrastination. They tempt us, because they easily combine with other shallow tasks and offer us a quick and easy reward: a ‘sweet marshmallow’. These temptations surround us daily. The consumption of social media, entertainment and news combines easily with performing other shallow tasks, while still providing a false sense of progress. The pull towards a multi-tasking lifestyle is understandable.

If you are used to such a lifestyle, the only way to really advance towards your goals is to part ways with it. I know, this is not easy to do, it will take some time, and you will experience withdrawal symptoms. I would not ask you to do this unless the benefits were significant.

Your goal is to become a serial single-tasker: someone who picks up one task at a time, gives it their full attention, and only then switches to the next task. To lose the multi-tasking habit, a good first step is to stop filling every moment of boredom with a shallow task, like habitually checking your phone for e-mails or messages. Instead learn to schedule activities like internet, e-mail and messaging. You need to start training your mind to prefer working on deep tasks over shallow ones.

A large part of this journey is unlearning habits that you have adopted that do not serve you well in terms of reaching your goals. We have to replace those habits with ones that will help you on a day-to-day basis: micro planning.

Micro Planning

Big Brother

If you are not yet actively planning your day, someone else most certainly is, and that someone may not have your best interest at heart. Many of us consume news, social media and entertainment on a daily basis. None of these things is bad in its own right, indeed they can be very useful. However, most people turn to these as ingrained habit, instead of as a conscious choice. These technologies are not neutral and engineered to foster such habit forming, playing into our desires and insecurities, usually with the end goal of monetization. This learned habitual behaviour interferes with our capacity to work on our own meaningful long-term goals, trading it for goals that are not our own, not in alignment with our interests, and even psychologically harmful. Fortunately, we can change our habits.

The List

Realize that the only real moment under your control is in fact the next moment in your life. It is there that you want to limit your choices beforehand, so you effectively steer yourself to work on tasks beneficial to your long-term goals. To this end, a useful habit to adopt is simply making a list of tasks to do for tomorrow at the end of the present day. Commit to actually writing this list down at the end of a day, and looking at it regularly throughout the next day, especially when you are at a loss as to what to do. View this as a small contract between your past and present self. Stick to the contract and you will learn to trust yourself.

Check off things you have completed on the list as you go through your day. Feel free to swap things around in your list if the day unfolds differently. Planning is in fact all about seeking flexibility within boundaries you set for yourself beforehand. There should be room for spontaneity.

The list approach provides three important things. Firstly, a flexible order in which you can do things, which avoids an imposed feeling. Secondly, a limitation on the number of choices you can make, which prevents choice paralysis. Thirdly, a tracking and reward system, which enables you to reflect on your day positively.

Expanding the List

A single daily list may not do as you pick up a more diverse range of tasks. Indeed, you may need an inbox with tasks to be sorted and a backlog with sorted tasks prioritized. Essentially though, these are all also lists. They hook into your overall planning process at a different point. These tasks too will eventually end up on a daily checklist, which continuously forms your central point of control.

As your planning process evolves, you may need to expand into creating a list for each day of the week. Whatever tools and setup you choose, make sure it meets these requirements: you should be able to,

  1. easily set and see what you should do next;
  2. see all the things you have already done;
  3. prioritize tasks that still need to be done;
  4. set deadlines on tasks (if applicable).
Organize, Track and Reflect

While a task list gives you an order in which to do things, it is not the best place to capture all the information regarding a task. For that you need to use something different. Ideally for each thing you are working on you maintain a separate ‘drawer’ of information. This can simply be a page in a notebook, a set of sticky notes, or an on-line alternative like Trello. Whatever you choose: it should be easy to access that information if you need to continue working on the task.

Estimating and tracking is important, as it the only way in which you can learn to estimate better and plan more realistically. For each task that takes more than a couple of hours, I suggest roughly estimating the total time you think you will need for it and tracking the time you put into it. Prevent getting caught up in details: do not plan or track more precisely than a quarter of an hour. The first couple of times you will be way off. This is fine, and also the point of doing it: to get better at planning.

Tracking time only is not enough. At the end of the week, gather all your daily lists, review them, and write some paragraphs about what went well this week and what can be improved for the next week in a journal. There is no need for deep analysis, keep things short and to the point, so reading it back later will be easier. This too will help you improve your planning process, which in turn helps you complete your goals more quickly and efficiently. Besides points of improvements, remember to actually write about and celebrate your successes.

A Word on Calendars

I have steered clear so far of calendars. While calendars are a good choice for scheduling meetings and appointments with others,  they are a rather poor substitute for planning your day. The reasons for this are simple. Firstly, if you plan your day ahead in your calendar in great detail, your plan is likely already outdated when you start. Priorities change, and tasks shuffle. A plan is dynamic and a calendar is generally too static to capture this well without it turning into micro-management. Secondly, planning in a calendar evokes more anxiety than necessary. If you blocked from ten to twelve to work on that hard math chapter, it may feel like you already failed when you start ten minutes late. A list allows you to plan the order of your day without imposing a strict time schedule.

Moment-to-moment

Now that we structured your day, set-up a filing system and a way to continuously improve your planning process by tracking and reflecting, it is time to bite the bullet: allocating actual time to tasks.

Firstly, I would like to encourage you to schedule an end time for each day: after this time you should stop working on the tasks on your list. The end time can vary each day, but it is important to decide on it beforehand. Secondly, realize your objective is not to cram as many hours in a day as possible. Instead, the objective is to be as productive as possible during a limited number of hours. Realistically, you may be able to work in a deep state for about six hours on an average day. Inevitably, unavoidable shallow tasks and required breaks will consume the rest of the time.

Eat a live frog first thing in the morning and nothing worse will happen to you the rest of the dayMark Twain

Starting with a deep task takes willpower. We usually start the day fresh, hence it is one of the best points in the day to utilize willpower. A good habit is to start on your toughest task as the first thing in your day, also called “eating the frog”. Follow this by easier tasks. Doing this beats doing it the other way around as that leads to postponing the hard stuff: procrastination.

Starting on any task can be challenging. However, having started, you may find it is not so bad after all. The trick then is to get started, to get over the initial speed bump, the initial reluctance. The more often you manage to actually do this, the easier it will get.

Tick-Tock

Get yourself over the bump by committing a limited fixed amount of time to the task: set a countdown timer and start working. This may seem strange, as an alarm guarantees a future interruption. While this is true, setting a timer also creates a choice-point for you in that near future: do I want to continue with this task, or move on to something else? The bounded time investment and the guarantee of an upcoming choice-point makes this approach powerful.

A commonly used starting point is to set a timer for twenty-five minutes, work in a focused state, and after that take a five minute break. During this break it is best to do something physical, such as getting a cup of tea, doing some stretches or taking a brisk walk. This countdown based approach is called the Pomodori Technique, named after the tomato-shaped timers that are often found in kitchens.

As you apply this method more often, experiment with different intervals instead of sticking to the fixed duration of twenty-five minutes. For example: sixty or even ninety minutes, followed by a longer break. The best interval depends on the task at hand. If you get into a state of flow, consider even disabling the timer. The most important function of the timer is to help you get started, and only to a lesser extent to stop you at some point in the future.

Getting Unstuck

What do you do when you get stuck? Do you try harder or give up entirely? Realize that neither approach is right, instead: stop temporarily. This can be a short as a five minute break, or as long as several days. During a short break do something physical which does not tax your brain, for longer stretches of time: simply work on other things. You should get back to the problem at a later time. This approach works remarkably well because it allows your subconscious to work on the problem in the background, while you do other things: diffuse-mode thinking.

Diffuse-mode thinking is what happens when you relax your attention and just let your mind wander. This relaxation can allow different areas of the brain to hook up and return valuable insights.Barbera Oakley
Habitual Tasks

Not all goals require equal attention all the time, some of them require daily dedication, others weekly and some only short stretches of very intensive work. I will refer to tasks that require some form of continuous attention as habitual and those that require short stretches as focused.

If you are learning an instrument you will have to attend to this daily. Pick a fixed moment in your daily schedule for this. For example: playing the instrument after you have breakfast. The goal is to develop a habit, to get into a routine: a system that takes away the cognitive load of having to make a choice. The time you spend need not be long. Half an hour a day translates into almost two whole working days a month. Picking an approach, and sticking to it consistently for at least thirty days, not breaking the chain, will automate the decision process.

This habitual approach works well for learning and producing things. Regularity is the key for progressing towards such goals. Consider that if you wake up every morning and write for thirty minutes before doing anything else, that may not amount to much in several days, but keep it up for a year and you will have put in a good hundred-eighty hours: more than four full-time workweeks.

Immersive Tasks

For projects that require a spurt of activity to complete: dedicate most of your time to them for a set period. Immerse yourself in them from several days up to one or two weeks. This can help put some pressure on finishing the task, instead of letting it endlessly drag on. That said: work on projects in an early phase is often best interleaved with work on other projects. This interleaving allows the early phase projects to incubate, giving you the time to learn the best way to progress on them. You can use this knowledge later on for that period of exclusive immersion.

Over time some goals may become more important. Other goals recede to the background, only to return to the forefront of your attention after a while. This is normal, and progress on projects that require longer immersive time often proceeds in waves. This in fine, as long as you do not stall completely. Try to always keep working on things a bit with some regularity. This way you leverage your unconscious processes to eventually produce better quality output.

Conclusion

Planning is personal. The approach you take should avoid overplanning and underplanning and work for you. Gradually enhance your planning process by integrating the ideas, principles and approaches presented in this article and other resources you find. This will take time and effort, but it is worth it. Moving towards your own goals, and learning to enjoy that journey more so than actually reaching the goal itself, is what planning should enable.

You know about the importance of committing regular time to your goals, taking small steps initially and constructing a larger plan with clear completion criteria as you go. You learned about the difference between shallow non-cognitively demanding tasks and deep distraction-free work. Becoming a serial single-tasker is your next challenge. You became aware that when you are not planning your day, someone else with different goals is, and that the anti-dote to this is a list-based planning approach, not a calendar. You realize a list is not enough, and that you need to track and reflect on the time you spent. Upon getting stuck you know you need to walk away temporarily. You also know how to properly allocate time by using countdown clocks, foster habit forming for long-term goals and immersive yourself in tasks nearing completion.

Let me end with a challenge to get you started: dedicate the next half hour to one of your dreams. Something that you have been thinking about picking up for a long time, but never actually seem to get to. Visualize it, hear it, feel it. After the half hour is over, either keep going if you are in flow, or plan the next moment you are going to get back to it. Now: just set a timer, think of the first step, and go!

Sources:

  1. Allen, D. (2002) Getting Things Done.
  2. Harris, T. (2014) Why Design Needs Ethics.
  3. Newport, C. (2016) Deep Work.
  4. Oakley, B. (2017) Mind Shift.
  5. Oakley, B. (2014) A Mind for Numbers.
  6. Schwartz, B. (2005) The Paradox of Choice.
  7. Tracy, B. (2007) Eat That Frog.

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