There may be evolutionary psychological factors that encourage modesty and mediocrity, at least in appearance; while some of that may still apply today, you should mentally plan and strive to pull ahead, if you are doing things right.
This post is part of a series rerunning Eliezer Yudkowsky's old posts so those interested can (re-)read and discuss them. The previous post was Tsuyoku Naritai! (I Want To Become Stronger), and you can use the sequence_reruns tag or rss feed to follow the rest of the series.
Sequence reruns are a community-driven effort. You can participate by re-reading the sequence post, discussing it, posting the next day's sequence reruns post, or summarizing forthcoming articles on the wiki. Go here for more details, or to discuss the Rerunning the Sequences series.