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Here is a collection of (hopefully) useful advice from a number of sources around the web. Slowly, I will put up my advice from my own experience, but at the moment the list primarily includes reference material that I have found useful. I try to give credit where credit is due, but let me know if something is attributed incorrectly or if a link is broken.

...for Caltech students

Orientation slides for the CS major (from 2013)
Option guidelines for PhD students in the CMS department

... on applying to grad school

Applying to PhD programs in computer science by Mor Harchol-Balter
What graduate schools want by Matt Might
Why go to graduate school and how to get in by Amin Vahdat
Graduate School FAQ by Mike Gleicher, Wisconsin-Madison
Advice for Undergraduates Considering Graduate School by Phil Agre
Graduate school info guide from the CRA
Applying to grad school in CS Slides by Adam Wierman

... on being a grad student

Managing your advisor by Nick Feamster
Advice to a beginning graduate student by Manuel Blum, CMU
How to have a bad career in research/academia by David Patterson, UC Berkeley
How to be a good graduate student by Marie desJardins, UMBC
How to write a good (no great) dissertation by Priya Narasimhan, CMU
Time Management by Randy Pauch, CMU
So long and thanks for the PhD by Ronald Azuma, UNC
Advice for Graduate Students in Statistics J. Michael Steele, UPenn
Writing and presenting your thesis dissertation S.J. Levine, Michigan State U.

... on writing papers

Conference acceptance statistics from Kevin Almeroth, UCSB
Three sins of authors in computer science and math by Jonathan Shewchuk, UC Berkeley
We are sorry to inform you by Simone Santini, UCSD
How to write a good research paper by Simon Peyton Jones, MSR
Mathematical writing by Donald Knuth
How to write a bad article by Fredo Durand, MIT
Storytelling 101: Writing tips for academics by Nick Feamster

... on giving a talk

How to present a paper by Ashwin Ram
Giving an academic talk by Jonathan Shewchuk, UC Berkeley
The cognitive style of powerpoint by Edward Tufte
Really bad powerpoint (and how to avoid it) by Seth Godin
In defense of powerpoint by Dan Norman
Giving a good technical presentation by Kim Fowler
How to give a good research talk by Simon Peyton Jones, MSR
Presenting a technical talk by Nick Feamster

... on refereeing papers

Self-plagiarism in computer science by C. Collberg and S. Kobourov
Notes on constructive and positive reviewing by Mark Hill and Kathryn McKinley
How to review Michael Bieber, NJIT
The paper review process by Nick Feamster

... on an academic job search

The Chronicle of Higher Education message boards
CRA Taulbee Survey
Academic job search: a practical overview, Stanford
The PhD job hunt - helping students find the right positions by Ed Lazowska
The "Job Talk" Talk Tom Wenisch
The N things I wish I knew before the job search
Tips on the interview process by Jeanette Wing, CMU

... for new faculty

Patterson's rules for new CS and Engineering profs by David Patterson, UC Berkeley
How to have a bad career in research/academia by David Patterson, UC Berkeley
Building a research career by Francine Berman, UCSD
Time Management by Randy Pausch, CMU
The dignified professor by Richard Feynman
Ten lessons I wish I had been taught by Gian-Carl Rota, MIT
21st century professor by Thomas Grose
You and your research by Richard Hamming
Research patterns by Nick Feamster

... on obtaining funding

You and your research proposal by Nick Feamster
Advice on writing NSF proposals by Susan Finger, CMU
How to write a good research proposal by Simon Peyton Jones, MSR
Guide for writing a funding proposal S.J. Levine, Michigan State U.
NSF CAREER proposal writing tips