Why is estimation so difficult?
Estimation is a very difficult task - depending on what is being estimated.
For the project we are on we have tried most of the "standard" ways of estimating work. We have tried man days, t-shirt sizing, story points and a bunch of others. However none of them proved particularly successful. The nature of the work we do is very varied and it is definitely not a cookie cutter exercise where we have work on similar tasks before.
This also applies to life. Derek Sivers makes a statement:
Most people overestimate what they can do in one year, and underestimate what they can do in ten years.
And there is definitely truth in this. We can look at the short term and make a long list of things we are going to achieve - and very likely we won't achieve anywhere near all of them. On the other hand, when we look back 10 years we can be amazed at how much we have achieved over that time.
I wish there was some magic piece of advice to distil here. I guess it could be rein in the short term and expand the long term aims.
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