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This question is related to an earlier question I asked Should I schedule my tasks with deadlines?

Recently, I've had break from work for two months, so I focused on my personal projects. My experience was that Parkinson's law is very real. In case of infinite time available, i.e. without deadline, tasks fill up infinite time and progress painstakingly slow. Procrastination and distraction become really big issues. So I've switched to scheduling and setting deadlines for my personal projects as well. For example, "read X pages from book Y by next Sunday".

One thing I was wondering about is if I should also set penalties for myself when I miss a deadline and what the penalty should be. Otherwise, I have a feeling that deadlines by themselves wouldn't be very effective.

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If there is no penalty - it's not a deadline.

That's the headline - but if we look a little bit deeper we might find that there are a lot of in-built penalties:

  1. Project is delayed - you set the deadline for a reason, and you also set it when you had a nice global big-picture view of where you wanted to be. If a project that you want to be successful is delayed then that's it's own penalty.
  2. Loss of face - in the outside world your penalty might be the loss of face or personal reputation in the eyes of the people who were expecting you to meet that deadline. For personal projects that aspect is still true, you are risking self-esteem and a certain amount of our own identity if you can't cope with your own deadlines.

Whoops - got to go! Back to expand later... edit Okay more..

So another issue to consider is flexibility - one of the very powerful things I got from Randy Pausch's Time Management talk about deadlines was this:

Never break a promise, but renegotiate them if need be. If you've said: "I have this done by Tuesday at noon", you can call the person on Friday and say, "I'm still go to my word but I'm really jacked up and I'm going to have to stay and work over the weekend to meet that Tuesday deadline. Is there any way there's any slack on that?" And a lot of times I say: "Thursday's fine." Because I really needed it Thursday, but I told you Tuesday." Or they'll say: "It's no problem, I can have Jim do that instead of you. He has some free time." Now if they say: "No, there's no wiggle room here", you say: "That's okay, no problem, I'm still go to my word."

which has been wonderful for flexibility in time management and for not letting people down. The problem with personal deadlines is that when you negotiate with yourself things can go very wrong - maybe this is why so many people have the thought process "I was going to start my diet today but X, Y and Z came up so I'll start tomorrow." As an example - I renegotiate my getting out of bed time on a regular basis. So I would try and make sure you have someone to be accountable to. Even if it's just a friend who is interested in your day. This can be the person who is willing to call you out when you move a deadline that you didn't have to.

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How about shifting this a little? Instead of a penalty, how about a reward? Upon completion of a task or phase, treat yourself. Maybe it's a slice of pie or maybe it's a ski weekend. The penalty (not getting your treat) is built-in. It'll be best if it's a predefined thing and that it's scale is appropriate. Make sure you follow through with yourself, though! Give yourself the carrot instead of the stick!

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I think formal commitment devices are the way to go for this sort of thing, so you can't later weasel out of your own penalty. If it's just a binary thing (I made the deadline or not) then you might like or if it's more of an ongoing thing, or something you can graph -- like spending so many hours per week on something -- then, IMHO, Beeminder is much better.

Either way, the commitment device locks you in to externally imposed consequences so that you are forced to take the deadlines seriously.

[disclosure, if it wasn't obvious: I'm part of Beeminder]

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How about shifting this a little? Instead of a penalty, how about a reward? Upon completion of a task or phase, treat yourself. Maybe it's a slice of pie or maybe it's a ski weekend.

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