The Common Problem with Planning (and why it makes you feel miserable)

Prediction makes us feel good as it gives the illusion that we know what will happen in the future and that conveys certainty and less risk. I once read of how the first weather forecasting service in Great Britain started in the 1700s, or thereabouts. It was hopelessly incorrect, being wrong on almost every occasion and so the service was stopped. However, there was such a backlash of complaints (and remember, this happened back in the days that you had to put pen to paper, buy a stamp and post your complaint, so the public must have been really riled), that the service was reinstated. Such is our thirst for the certainty that we think that prediction can give us.

Most personal and business plans focus heavily on predicting how long it will take to get something done and to finish it. Most of the time these predictions are wrong, but few people learn from this and do something about it. However, there is an enormous downside to inaccurate prediction that generally goes unnoticed.

When we create time estimates for when things will finish, we set up new objectives and expectations. When we fail to achieve these objectives we end up feeling bad. We then either rage against reality for not meeting our predictions, or against ourselves for proving inadequate. These are, in fact, ridiculous stances to take, but it happens very commonly. The real problem is that creating a plan based primarily upon time estimates and expecting it to be right actually designs failure into the whole effort.

When you look up the word ‘plan’ in the dictionary or thesaurus, no mention of time is given. Most descriptions and synonyms refer to process and organization. An action plan should not initially focus on the time taken to do something. It should focus on the process required to get something done. You can only get a job done by carrying out every single point of the process that gets the whole job done. If you overlook any single part, then the job will not get done.

Where most people go wrong with personal planning is that they set an objective and then give a time estimate for how long it will take to complete the job. If you have never done a particular task before, or if it’s something that you’ve done before but it requires new aspects of problem solving, then your time estimates will, more often than not, be very inaccurate. In my experience, most people underestimate the time by by half, i.e. it takes twice as long to do as they expected.

With this kind of plan, you set off with a poorly thought out process in place for getting things done, encounter all sorts of problems, get waylaid and frustrated, fail to meet your targets and then end up feeling annoyed, or even miserable with yourself. Once again, reality failed to bend to your will.

If you want to create a useful plan, then proceed as follows:

* start by identifying and describing your objective very clearly

* work out the major activities, or subtasks, required to reach the end point

* split those those activities into the different types of work needed. For example, when working alone, think of the different modes of thinking that you require (creative/imaginative, analytical, compositional, procedural, organizational, productive) and divide the work accordingly

* consider the resources needed (skills, materials, equipment, services and so on) and their availability

As you go through this process you are, in effect, carrying out the task, in principle, in your mind and as you do this you get a better idea of the order in which things must be done as well as what you need to get things done. The most vital thing to take note of are the foreseeable difficulties. These are the things that will block your progress, usually because you don’t have a possible solution to move you forward, or you lack the personal skills, knowledge, experience, process necessary, or you don’t have the physical resources necessary to get the job done. If you don’t identify these things in advance, then when you reach them you will grind to a halt - guaranteed.

When you have planned, i.e. designed your process for getting things done, in sufficient detail that you know all of the things that combine together to create the finished thing and you have identified and solved the foreseeable, or likely, problems, then you can start. You might still feel the urge to put time predictions onto things for the convenience of planning your day, or week, but never let the time estimate determine whether you feel successful, or not. Success comes from getting the end result, and that is done by completing the whole process that takes you there. The prime focus is always upon progressing with the process. If it takes longer than you wanted, then you either have to accept the lateness, or else give up when the time runs out.

Accurate time predictions for things that you’ve never done before, or don’t repeat often, is fiendishly difficult. By focusing on designing a full and accurate process for getting the work done, you focus on planning for an accurate reality, rather than stressing yourself out with imaginative, but highly inaccurate timescales as the determining factor for how you carry out the work and how your judge your performance.

The most important thing to identify and focus upon with your planning are the real hard difficulties that you will have to get through. This is where planning has the greatest effect for allowing work to progress smoothly. By identifying these problems in advance and by working out solutions for them, in principle at least, you prepare yourself to cope with the worst of what is to come. Most people don’t do this. They pay little attention to these things and then, when they reach that point where progress is impossible, they find themselves frustrated. This leads to the generation of negative emotions, which tend to drive people into procrastination and into feeling inadequate. In the worst case, it can lead to putting in a lot of effort, only to arrive at a hold up that is just too big to overcome. This is leads to paralysis and very often it finally leads to quitting. If you have already put a lot of effort into something, then this a tragic event.

On a day to day level, the ‘How To Do‘ list turns an ordinary ‘To Do’ list into an effective process for getting things done during the day and it focus on that especially important point of identifying and dealing with barriers to progress in advance of going into action.


The guiding principle behind the writings on is that if you are emotionally well-balanced, then you naturally want to engage in carrying out useful and productive activities. If not, then you will struggle against yourself to get things done. This reduces your efficiency and your effectiveness and, at times, it leaves you immobilized and unable to get anything done on important, yet difficult issues. There are four key topics that remove the resistance to getting things don...

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