It seems I keep missing deadlines I set myself. I’ve been wondering why this is, and come up with a couple of reasons:

I’m almost always treading new ground
This means that I’ve no or very little experience to draw on when I’m making my estimates.

I feel pressured to estimate lower than I think realistic
Wishing to please I will say two to three days when my subconscious is screaming that a week is more likely.

I often don’t have time to make a qualified guess
I’m often asked to make ball-park estimates off of the top of my head, which makes me rush through and reach a result where I haven’t calculated with everything that needs to be done.

I procrastinate
I usually jump into a task working with great focus for the first while. Then, having made good progress, and knowing I don’t have to deliver until next week, I feel I can spend a couple of days just fiddling around, getting distracted and such. Problem is, the feeling doesn’t go away as the deadline nears.

And finally:
I get away with it on a regular basis
I’ve yet to be even reprimanded for missing a deadline. Not at school, nor at work has anyone scolded me for missing an assignment. Learning that I could get away with it, I prioritized my time differently.

Wanting to change this, I think I’ll have to work on each of these points.

Treading new ground is in my circle of concern, but not so much in my circle of influence, which means I can’t change the fact that I’m often working with new things. It’s what I love doing, even. I can, however, stall the estimate until I know some more about the technology and the demands.

Trying to please by estimating low is in my circle of influence. I have to remember that when I say something takes a week, it’s going to take a week no matter how much you need it tomorrow, and I’m not really pleasing anyone by not delivering when they expect it. Plan with the end in mind, I guess.

The having time issue is partly in my circle of influence. I can refuse to do ball-park, which isn’t going to work, or I can calculate with a buffer of sorts, something which I should probably do in all my estimates.

Procrastination is totally in my circle of influence. Nothing outside of me can change that. I have to work on doing first things first, getting important things our of the way before they become both important and urgent.

Getting away with it is only a problem as long as all the other things are. If I don’t underestimate my tasks, and always deliver on time, I won’t need the habit of getting away with missing deadlines.