Two Ways to Step Up to Meet a Deadline

Image of an hourglass nearly out of time against dark blue background
A deadline is the date a task needs to be finished. It is different from an estimated completion date in that there are real negative consequences for missing the target.
For example, the deadline for filing taxes in the US was May 17 this year.  The penalties are spelled out in advance for failing to do so.
Similarly, many people set a deadline to complete important tasks before they go on vacation. They know that if they don’t wrap up critical tasks before they leave, they risk being interrupted during the vacation or coming back to a mess.
Sometimes people take deadlines seriously only when they are set by other people. But a deadline is real even when you have total control over it. I gave myself four hours to write this newsletter.  I could have budgeted more time, but this was an appropriate amount for the task.  If I hadn't finished this article in the four hours allotted, I would have been cannibalizing time from other priorities.
So how do you make sure you meet a deadline? I've investigated many aspects of this question over the years. Clearly, you need to know enough about the project to accurately estimate the time it will take. Otherwise you set yourself up for failure. And you need to make real to yourself the consequences of not finishing. You may also need to have contingency plans for how you will finish if things don't go as planned. These are all learnable skills.
But even if you have set a very reasonable deadline, there is another element of success. You need to shift your mind into gear to jump into the work to get it done in a timely way.
Most people do this by applying pressure to themselves. They focus on all of the terrible consequences that will happen if they don't finish. They use the fear of those terrible consequences to push out anything else from their awareness. If you feel "stress" at work, this is how you are meeting your deadlines: by girding your loins, blocking out everything except the task at hand, and concentrating on it.
If you have read my work for a while, you know that I object to that method of getting things done on several grounds. For one thing, it involves suppressing anything unrelated to the task at hand. This creates long-term motivational damage, in that you associate tension with important work, you block out awareness of your other values, and you overuse willpower. You end up exhausted and unhappy even if you meet the deadline. Worse, pressure only enables you to get routine work done. When the project requires any kind of creativity, pressure kills your ability to do the work. Pressure is a frequent cause of creative blocks.
For a long time, I thought all you needed to do was to increase the value of doing the work and finishing. All of the other strategies I mentioned earlier (understanding the goal, clarifying the consequences of missing the deadline, working out contingencies) are designed to strengthen your values and help you hold them in mind. But they don't necessarily propel you into action, right now, to ensure you finish by your deadline. When you focus only on values-clarification, you can use up all of your time clarifying what is important. Believe me, I have done this.
You need a mental set that keeps your sense of urgency without blocking out awareness or overwhelming you.
But in addition, you need a mental set that answers thoughts like, "I'm not sure this really is the most important thing to do. Maybe I should spend more time figuring out my priorities" or "Why don't I just take some extra time to make this higher quality. It will be better" or "I don't really feel like doing this right now, so I'm probably not going to be as effective at this work." You know these thoughts. They are the thoughts that lead you into procrastination and perfectionism, and you can bet they will occur to you on this task, too.
You need a mental set that infuses your intention with determination to finish by the deadline. The best way I've found to do this is to affirm three essential thoughts before I start work:
1. "This task is going to be unpleasant in the short term, but I can handle the unpleasantness because I see how important this task is."  
You can handle unpleasantness. You have turned in work that is lower quality than you prefer. You have done tasks when you were tired or uncomfortable or feeling lousy. You just need to keep in mind that this is one of those times when the unpleasantness (not pain, strain, or suffering) is a part of the commitment. Reminding yourself that you can handle this predictable obstacle answers any moaning and groaning while also generating the emotion of confidence.
2. "In fact, I hereby embrace any unpleasantness because I need to become more aware, not less, of what's getting in the way of doing this on time. I will introspect any negative affect to reveal the underlying values. So, I'm investing in my future, knowing I will untangle this issue and grow my skill as a result."
There is a subtle shift when you accept the unpleasantness. You recognize that you are using your mind to do this work. You are committed to strengthening the values you have chosen to pursue. Acting to gain them despite unpleasantness will strengthen your emotional resilience, which will make all these situations easier. It will also reveal exactly the things you need to know to make this work more pleasant in the future. The unpleasantness is in fact just growing pains, and you value growth.  This reasoning is an application of the virtue of pride at work. When you believe it, you feel the corresponding emotion of pride.
3. "In order to finish this task on time, my normal methods are not going to work. I see that because of the slips in the schedule so far. Therefore, I need to shift the status quo. I need to put in a burst of effort to gain the values related to timeliness here. I need to invest my energy to break through whatever residual barriers are stopping me from making the decisions, taking the steps, and/or reaching closure."
This final statement couches the situation in terms of fighting for your values. This triggers a positive anger directed at obstacles rather than at people. It helps you to concentrate through forward momentum rather than blocking out other thoughts. Activating this kind of anger is how I got my master's thesis finished at MIT. I realized if I didn't shift into gear during spring break to finish the third draft, I wouldn't get through the necessary approval cycle by the deadline to graduate. That thought made me feel mad, and I turned on the power and finished.
This mental preparation, by its nature, activates feelings of confidence, pride, and a hint of anger that all motivate you to focus on completion.
Three guesses as to which method I recommend you use. Determination is a method based on increasing awareness, not reducing it. It uses that burst of willpower to fight for your values rather than fight off "enemy" thoughts.
The difference in short- and long-term results is profound.
When you take action under pressure, you feel like a victim, you increase your level of stress, and you feel only a temporary relief when you meet the deadline. You know you'll be back under pressure again soon and it will be just as bad or worse. You feel like you need some time off just to recover.
When you take action using determination, you feel in control, you grow your emotional resilience, and you have a sense of victory when you meet the deadline. You are energized by the effort and ready to turn your attention to the next project on your schedule.
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