Effort, Pain, and Looking Stupid (2020–2021)

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.