Here's a fun format: get a big white board, and write the years of the 21st century. Write a category; something that has many variations come out every year. Next, write your picks or favourites. Now invite everyone attending to replace a year's pick if they want and replace it with something they like.
This was a rolling game played last month at Lighthaven. I put up “Best blog post of every year” when the opportunity arose.
2000
My pick: Painless Software Schedules
This Joel SPolsky piece is applicable to far more than software. It's been the foundation or ancestor of all my good project management.
Crowd pick: Why the Future Doesn’t Need Us
Billy Joy writes with foresight about new technologies and their ethical dimensions.
2001
My pick: Suck in the Middle with Bruce
A stream of conciousness, half manic fever dream, half calculatingly ruthless ode to victory. Don’t worry about the Magic: The Gathering details, they don’t matter.
Crowd pick:
2002
My pick: Taste for Makers
Paul Graham had not yet learned brevity, but he had learned design. This is a beachhead of aesthetic - perhaps just the legible outcrop into software engineering.
Crowd pick:
2003
My [...]
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Outline:
(00:39) 2000
(00:42) My pick: Painless Software Schedules
(00:56) Crowd pick: Why the Future Doesn't Need Us
(01:07) 2001
(01:10) My pick: Suck in the Middle with Bruce
(01:27) Crowd pick:
(01:30) 2002
(01:34) My pick: Taste for Makers
(01:49) Crowd pick:
(01:52) 2003
(01:56) My pick: Welcome To The Site
(02:13) Crowd pick:
(02:16) 2004
(02:20) My pick: What You Can't Say
(02:33) Crowd pick: Mind the Gap
(02:53) 2005
(02:57) My pick: Fable of the Dragon Tyrant
(03:11) Crowd pick:
(03:14) 2006
(03:18) My pick: The Martial Art of Rationality
(03:33) Crowd pick:
(03:36) 2007
(03:40) My pick: Policy Tug of War
(03:54) Crowd pick: The Alameda-Weehawken Burrito Tunnel
(04:10) 2008
(04:13) My pick: Security Mindset
(04:29) Crowd pick: 37 Ways Words Can Be Wrong
(04:40) 2009
(04:43) My pick: Descent: The Game That Ruined Me
(05:01) Crowd pick:
(05:04) 2010
(05:08) My pick: Ureshiku Naritai
(05:26) Crowd pick:
(05:30) 2011
(05:33) My pick: Hack Away At The Edges
(05:47) Crowd pick: The Alouside Boytmend
(05:56) 2012
(06:00) My pick: Participation in the LW Community Associated With Less Bias
(06:22) Crowd pick: Salary Negotiation: Get paid more, be more valued
(06:47) 2013
(06:50) My pick: The Lottery of Fascinations
(07:05) Crowd pick:
(07:08) 2014
(07:11) My pick: The Control Group Is Out Of Control
(07:29) Crowd pick: Meditations on MOloch
(07:44) 2015
(07:47) My pick: Not Because You Should
(08:01) Crowd pick: The Value Of A Life
(08:23) 2016
(08:26) My pick: The Pyramid and the Garden
(08:40) Crowd pick: A Possible Way To Achieve All Your Goals
(08:50) 2017
(08:54) My pick: Melting Gold, and Organizational Capacity
(09:08) Crowd pick: The Face Of The Ice
(09:28) 2018
(09:31) My pick: Write a Thousand Roads To Rome
(09:46) Crowd pick:
(09:49) 2019
(09:53) My pick: Asymetric Justice
(10:08) Crowd pick:
(10:11) 2020
(10:15) My pick:
(10:18) Crowd pick: Pain is Not the Unit of Effort
(10:32) 2021
(10:36) My pick: Self Integrity and the Drowning Child
(10:49) Crowd pick: Willingness to Look Stupid
(11:06) 2022
(11:10) My pick: Sazen
(11:25) Crowd pick:
(11:28) 2023
(11:32) My pick: Things I Learned By Spending Five Thousand Hours In Non-EA Charities
(11:51) Crowd pick:
(11:54) 2024
(11:58) My pick: Situational Awareness
(12:17) Crowd pick: No Good Along
(12:47) 2025
(12:50) My pick: On Priesthoods
(13:02) Crowd pick: An upcoming post by one of Inkhaven Residents
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First published:
November 30th, 2025
Source:
https://www.lesswrong.com/posts/6xa372sg77jL5gWti/a-blogger-s-guide-to-the-21st-century-1
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Narrated by TYPE III AUDIO.
LessWrong (30+ Karma)