Say you throw a single fair die, what is the probability you get a 6 on your roll?
Now say your throw the same die ten times recording the result of each roll. What is the probability that you will have at least one 6 recorded on your sheet of paper?
If that six is say a great work of art, people will usually not care about all the other 1-5s you accumulated in the search for your six.
If however someone is grading you on both your positive and negative outliers, perhaps a game where your score is equal to the average of all dice throws, you won't be better off with a set of a 100 die throws than with a set of just one die roll. Indeed if you had a tournament with that game, all the champions (and all the worst losers) would be people who threw the die just once, because 100 dice rolls with an average result of 6 are far more improbable than a set of one die roll with an average result of 6.
http://www.codinghorror.com/blog/2008/08/quantity-always-trumps-quality.html
For some reason it just seems we in particular could learn something from this anecdote.
Iterate more. The practice effect is your friend as is mining out positive outliers in really huge sets. I wanted to also mention something about using going meta as a way to procrastinate but I feared I would summon a Newsome.
Edit: This has been mentioned before. I think it is good to remind people of it. Desrtopa writes:
It is therefore best to assume this is a parable.