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I don't try to find out how long it will take but how to do it. So the first time the item is on the list is 'How can I do this?', and it will transform from there. Each time it counts as a full-blown task. Usually there are some older items as well where no further overhead is needed and which are well-known. And I feel ok if I get 3-5 in total done. (Simple ones are 'Do the laundry', 'write this email where you know exactly what to write'.)

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