A curated list of articles & books that effected my thinking, updated periodically. They tend to live at the intersection of technology, community, & culture. They are in no particular order beyond their chronological headings. Linking something here doesn’t mean I endorse every thought in it, of course.

2021-2023

• His software sang the words of God. Then it went silent. (S.I. Rosenbaum)
• A year of new avenues (Robin Sloan)
• 6 months with GoLang after many years with PHP (Dan Gurgul)
• On sarcasm (Boz)
• How Complex Systems Fail (Richard I. Cook)
• Software Engineer Manager Roles (Octopus Deploy)
• SOLID Principles of Object-Oriented Programming Explained in Plain English (Yiğit Kemal Erinç)
• Stop Measuring Community Engagement (Michael Hall)
• Site: Customer Experience Musings (Evan Hamilton)
• Revisiting the public commons (Deb Schultz)
• I Was Wrong About Mastodon (Marcus Hutchins)
• View a SKU (Cory Doctorow)
• My Ideas For Improving Alt Text Features On Social Media (Veronica Lewis)
• Video: The War for the Soul of Open Source (Adam Jacob)
• Hiring Software Engineers? 7 Engineering Leaders Share Their Biggest Lessons (Carmo Braga da Costa)
• How to run a small social network site for your friends (Darius Kazemi)
• The Matrix Holiday Update (2022) (team)
• Why Nintendo’s Satoru Iwata refuses to lay off staff (2013, Colin Campbell)
• The Ed Sheeran Problem, or, How the Record Industry Got What It Asked For (Cory Doctorow)
• Pay It Backward (Matt Ruby)
• Removing the stigma of a CVE (Madison Oliver)
• Book: Inclusive Design Communities (Sameera Kapila)
• Book: You Deserve a Tech Union (Ethan Marcotte)
• Don’t work with psychopaths (Livia Labate)
• An Engineering Manager’s Bill of Rights (and Responsibilities) (Emily Nakashima)
• I’m not fucking about, I’m internalising (Samir Talwar)
• Proof That Positive Work Cultures Are More Productive (Emma Seppälä and Kim Cameron)
• Reimagining how we think about career development (Amy Chantasirivisal)
• The Year in Design (2015) (Jeffrey Zeldman)
• The Coach and the Fixer (Rands)
• PDF: Sludge for Good: Slowing and Imposing Costs on Cyber Attackers (multiple)
• The Tyranny of Structureless (Jo Freeman)
• 7 Fatal Flaws in the Software Engineering Industry (Elso Kant)
• Best Practices for Gender-Inclusive Content Moderation (Alice Hunsberger)
• You Can Only Maintain So Many Close Friendships (Sheon Han)
• From IC to Engineering Leader: 3 Essential Lessons (Elso Kant)
• I don’t want to do front-end anymore
• Content debt (2016, Melody Kramer)
• How to Eliminate Organizational Debt (Aaron Dignan)
• Why are hyperlinks blue? (Elise Blanchard)
• The Big Picture (Mark Rosewater)
• Laziness Does Not Exist (Devon Price)
• I Hid My Disability At Work For 6 Years (Jill D. Griffin)
• Why open source projects should embrace operational transparency (Julia Ferraioli)
• Building For The 99% Developers (Jean Yang)
• Shields Up — Emergency Enhancements to Security Procedures (Krebs Stamos Group)
• Trapped In Silicon Valley’s Hidden Caste System (Sonia Paul)
• Is Our Definition of Burnout All Wrong? (Eve Ettinger)
• The art of the tick tock doc (Lara Hogen)
• Fire me if you have to (Raw Signal Group)
• The Mortifying Ordeal of Pairing All Day (Nat Bennett)
• Introducing the Public Interest Internet (Danny O’Brien)
• Why the Hybrid Workforce Requires the Geriatric Millennial (Erica Dhawan)
• Joe Swanberg is running a secret VHS rental shop from Ravenswood pizzeria (Emma Krupp)
• The Art of Managing Stakeholders Through Product Discovery (Teresa Torres)
• Drunk Post: Things I’ve learned as a Sr Engineer (u/flipstables)
• This one email explains Apple (Matthew Panzarino)
• This is the Awful Voice Inside My Head (on employee intimidation) (Charlie Warzel)
• PAGNIs: Probably Are Gonna Need Its (Simon Willison)
• The End of Agile (Kurt Cagle)
• 8 ways to create psychological safety in the workplace (Greg Barnett)
• Site: What Web Can Do Today?
• “Emotional strip-mining”: Sympathy sockpuppets in online communities (Devon Greyson)
• The Most Common Type of Incompetent Leader (2018, Scott Gregory)
• Peter Thiel’s Origin Story (Max Chafkin)
• File Not Found: Student who grew up with search engines (Monica Chin)
• Iceland’s Trials of a 4-Day Workweek (Villegas & Knowles)
• AMP Has Irreparably Damaged Publishers’ Trust in Google-led Initiatives (Sarah Gooding)
• A vision for a social model of open source (Julia Ferraioli)
• Standards Slip Slowly At First, Then Rapidly (Richard Millington)
• You aren’t your user (Laura Klein)
• Published Assets? We Had a Few (Doug Donohue)
• Mastering the art of workplace well-bring: 5 lessons from Denmark (Laetitia Vitaud)
• How to defend good code (Jason Swett)
• Jeans, Jorts, and Tough Feedback (Lara Hogan)
• PDF: Community Interaction and Conflict on the Web (multiple)
• Case Study: How FeverBee Tripled A Community’s Retention Rates (Richard Millington)
• Fear of getting noticed (Jeffrey Zeldman)
• The unreasonable effectiveness of simple HTML (Terence Eden)
• 3 points you should have paid attention to in the Spotify Engineering Culture videos (Jason Yip)
• Move over Javascript (Klint Finley)
• The good, the bad, and the ugly of making decisions in open source (Juan Pablo Buriticá)
• 5 Secrets to Community Onboarding (Michelle Knight)
• The hottest hire is still the Chief People Officer (Jess Yuen)
• How to create luck (Shawn Wang)
• Why are there so many tech layoffs? (2022, Melissa De Witte)
• Social Quitting (Cory Doctorow)
• We come to bury ChatGPT, not praise it (Dan McQuillan)
• I don’t want to log into your website (Elizabeth Lopatto)
• Disciplined Making (Matthew Cheney)
• The library is a safe place (Will Wheaton)
• It’s Not the Bike Lane’s Fault You’re a Bad Driver (Collin Woodard)
• New Questions on the Impact of Technology (2011, Al Erisman)
• The Cult of the Founders (Henry Farrell)
• Tiktok’s enshittification (Cory Doctorow)
• Belonging isn’t enough (Mandy Brown)
• The maddening saga of how an Alzheimer’s cabal thwarted progress (Sharon Begley)
• Podcast: Fostering Inclusivity for Neurodivergent Community Members (Patrick O’Keefe)
• Companies oversold 5G. It won’t be the last overhyped tech (Shira Ovide)
• Let the Platforms Burn (Cory Doctorow)
• The End of the Honest Internet (Ed Zitron)
• The Last Page of the Internet (Alex Pareene)
• The Coming Enshittification of Public Libraries (Karawynn Long)
• Why Open Source Matters (Stephen O’Grady)
• On Craft (Cat Hicks)
• Shmile (Ava Zeldman)
• Why We Don’t Recommend Ring Cameras (Adrienne So)
• The ABCD Method: Building Rapid Communities in Smaller Groups (Richard Millington)
• The invisible problem (text editing on mobile) (Scott Jenson)
• The Web Is for User Agency (Robin Berjon)
• Let’s Make Sure GitHub Doesn’t Become the Only Option (Edward Loveall)
• Web developers: Remarkably untalented and careless? (Baldur Bjarnason)
• Loved, yet lonely (Kaitlyn Creasy)
• Why I Tend Not To Use Content Negotiation (Carson Gross)
• KPI Trees (Christoph Steinlehner)
• Why I Don’t Dig the Singularity (Sara Amis)
• Dominaria Cartography (2018, Ethan Fleisher)
• Rethinking Engagement Analytics (Rachel Happe)
• Most breaches actually begin in corp (Ariadne Conill)
• The birth & death of search engine optimization (Xe Iaso)
• Software Is Beating The World (Ed Zitron)
• The Importance of Silos (Dave Snowden)
• CUPID — the backstory (Dan North)
• Open Source Licenses: Who Holds The Power? (Jennifer Higgins)
• How Do You Foster Trust? Moderation Is Not Enough (Rachel Happe)
• A Secret Society of Chicago Bakers (Jennifer Billock)
• The reckless, infinite scope of web browsers (Drew DeVault)
• How We’ve Compromised 10 CI/CD Pipelines (multiple)

Mar 2021

• Things your manager might not know (Julia Evans)
• They can’t even fire us right (Jack Crosbie)
• Programming Sucks (Peter Huntwelch, 2014)
• Why project managers get no respect (Scott Berkun)
• On Context: The Cambridge School and Curt’s jacket (Leda Glyptis)
• Institutional Betrayal and Institutional Courage (Jennifer J Freyd, PhD)
• Charm Your Communities (Victoria Tran)

Feb 2021

• [Book] The Art of Leadership: Small Things, Done Well (Michael Lopp)
• How Deflector became a media success (Margaret Sullivan, NYT)
• Reflecting on a year of Alpine Parrot (Alpine Parrot)
• Founding Growth Lead (Amazingly-composed job posting @ Commandot, via Jennifer Kim)
• 8 Interview Questions About Diversity & Inclusion Every Job Seeker Should Be Able to Answer (Kelli Newman Mason, TheMuse)
• How Avocode Improved Dev Process 10x with Shape Up (Josef Kettner)
• How money dictates design decisions (Jonas Downey, Hey.com)
• [Scrum] Why relative estimation beats planning poker (Joel Bancroft-Connors, Applied Frameworks)
• I’m a Short Afternoon Walk And You’re Putting Way Too Much Pressure On Me (Emily Delaney, McSweeney’s)

Jan 2021

• They left Mozilla to make the internet better. Now they’re spreading its gospel for a new generation (Anna Kramer, Protocol)
• Hotwire: HTML Over The Wire (Josh Graham)
• What Tracy Chou learned about online harassment while building an app to solve it (Anna Kramer, Protocol)
• The 5 Commandments of Naming Variables (Khalal Walker)
• We Are Not Special [Engineers vs Engineers] (Killel Wayne)
• Understanding Incidents: Three Analytics Traps (John Allspaw)
• Singletons and their use in WordPress (Carl Alexander)
• Expensify CEO David Barrett: ‘Most CEOs are not bad people, they’re just cowards’ (Benjamin Pimentel, Protocol)
• 21 Signs You or Your Organization May Be the White Moderate Dr. King Warned About (Vu Le, Non Profit AF)
• PHP 8.0: A Perfect Storm (Juliette Reinders Folmer, 24 Days In December)
• Twitter thread: Foundational work in regulating online speech (Alex Stamos)
• Make Boring Plans (Camille Fournier)
• Resilience engineering: Where do I start? (Lorin Hochstein)
• Conditions For Learning [Everyday, vs During Incidents] (Erik Hollnagel, HindSight)
• Meaningful Questions to Ask People Right Now (Marina Khidekel, Thrive Global)
• When Black Women Go From Office Pet to Office Threat (Erika Stallings)
• Error Budgets and the Legacy of Herbert Heinrich (Lorin Hochstein)
• Facebook Is a Doomsday Machine (Adrienne LaFrance, The Atlantic)
• [Shot] Video: Commercial Open Source Business Models (Brendan O’Leary)
• [Chaser] GitLab Removes Its Starter Tier: Pay 5x or lose features (Tim Anderson, The Register)
• OSL 3.0 Explained (Lawrence Rosen)
• A Quick Political History Of White Supremacy (Steven Conn, HuffPost, 2017)
• You’re Using Transients Wrong [In WordPress] (Ryan McCue, 2013)

Jun-Dec 2020

• Book: Working in Public: The Making and Maintenance of Open Source Software (Nadia Eghbal)
• Hotwire: HTML Over The Wire (Basecamp)
• Second-guessing the modern web (Tom MacWright)
• 100 Years of Voting Hasn’t Done What We Thought it Would (Gail Collins, NYT)
• Why Black People Don’t Go Camping (Nikki Brueggeman, Medium)
• Why Redis beats Memcached for caching (Itamar Haber, Infoworld)
• A Sneaky Theory of Where Language Came From (Ben James, The Atlantic)
• The culture of hurry: the value of ‘free’ work time (Erin ‘Folletto’ Casali)
• Measuring Engagement & Culture (Rachael Happe, TheCR)
• Communities Change How We Work (Rachael Happe, TheCR)
• So Much Community Data, So Little Insight (Rachael Happe, TheCR)
• How Open Source Communities Work (Stormy Peters)
• Many Games Are Held Together By Duct Tape (Patricia Hernandez, Polygon)
• The Anti-Capitalist Software License (Ramsey Nasser & Everest Pipkin)
• Future of Cygnus Solutions (Michael Tiemann, 1999)
• The Cost of Workaholic Leaders (Suzan Bond)
• Sticking To It (Zeldman, Automattic)
• Building The Woke Web (Olu Niyiawosusi, ALA)
• Implementing Shape Up (John Stokvis)
• An Incomplete Guide to Inclusive Language for Startups and Tech (Courtney Seiter, Buffer)

Jan-May 2020

• Responsive Design Turns Ten (Ethan Marcotte)
• Open Source Beyond The Market (DHH, SvN)
• Is Your Work Truly Essential? (James Kaelan, Medium)
• On Mid-Career and Thinking About Your Path Forward (Ryn Daniels)
• Laziness Does Not Exist (Devon Price)
• Feedback Ladders (Leslie Cohn-Wein, Kristen Lavavej & swyx, Netlify)
• The Old Internet Died And We Watched And Did Nothing (Katie Notopoulos, BuzzFeed)
• Why Developers Hate PHP (Mehdi Zed)
• Book: It Doesn’t Have to Be Crazy at Work (DHH & Jason Fried)

2018-2019

I didn’t regularly update this list for a couple years, so this is a retroactive list.

• Book: Crucial Conversations
• Book: After the Ecstasy, the Laundry (Jack Kornfield)
• Book: Generation Decks: The Unofficial History of Magic the Gathering (Titus Chalk)
• Book: The Manager’s Path (Camille Fournier)
• The Imbalance of Culture Fit (Matt Griffin, ALA)
• Mental Illness in the Web Industry (Brandon Gregory, ALA)
• Video: How to Keep Your Systems Running Day After Day (John Allspaw, Devops Ent. Summit)
• Video: Explaining Kanban Using Kanban (Eric Brechner, Talks@Google)

Jul 2017-Feb 2018

• The Difference Between Amateurs and Professionals
• Want readers to start trusting you again? Stop stalking them across the internet
• Improving Our Engineering Interview Process
• Backyard Pond
• Advanced query optimization techniques on large queries
• Top 20+ MySQL Best Practices
• Hacking, Refactoring, Rewriting, and Technical Debt
• You are the product
• I significantly underestimated the power of Jeff Bezos
• Join our startup, we’ll cut your pay by 40%!
• Sleeping barber problem – Wikipedia
• Face ID, Touch ID, No ID, PINs and Pragmatic Security
• Just 22, this digital news publisher is ready to go old-school with print
• Reddit’s campaign against hate speech worked
• Refresh Is Sacred
• Software is a Long Con
• On Improving Diversity in Hiring
• Why open source software isn’t as ethical as you think it is
• Whom the Gods Would Destroy, They First Give Real-time Analytics
• The Week My Husband Left And My House Was Burgled I Secured A Grant To Begin The Project That Became BRCA1
• The privilege of risk
• We fired our top talent. Best decision we ever made.
• The Web began dying in 2014, here’s how
• AMPersand
• When we only hire the best means we only hire the trendiest
• We’re making Slate’s advertising as smart as its content.
• Do Facebook and Google have control of their algorithms anymore? A sobering assessment and a warning
• May the next Etsy learn its lessons
• How to prepare for a one-on-one meeting as an employee
• The Mortality and Joy of Productivity
• Oh, shit, git!
• Net Promoter Score Considered Harmful
• How To Create A Useful Value Proposition w/ Examples
• “username or password incorrect” is bullshit
• The presence prison
• Why Good Managers Are So Rare
• So Now You’re A Manager
• How good code dies
• How to crush remote team retreats
• DOES17 (conf talk video) – How Your Systems Keep Running Day After Day
• Stimulus 1.0: A modest JavaScript framework for the HTML you already have
• Better Onboarding, Better Retention, Happier Humans
• Is PHP relevant?
• Everything Easy is Hard Again
• Why supporters pay for journalism (hint: it’s not about exclusive access)
• A beginning consultant brings skills, an experienced consultant brings value
• Be a Pal, My Dudes
• Who I want to work for

Mar-Aug 2017

• Product Roadmap Prioritization: Weighted or Kano?
• 20 Product Prioritization Techniques
• JWT (JSON Web Tokens) is a Bad Standard
• Index cards are pretty cool
• Why Employees At Apple And Google Are More Productive
• Anthony Bourdain Does Not Want to Owe Anybody Even a Single Dollar
• Front-end Developer Handbook 2017
• 6 Rules To Live By When You Work In An Office But Have Remote Team Members
• Fog Creek Professional Ladder
• What is the best way to evaluate a software engineer?
• JSON Feed
• Why I Never Let Employees Negotiate a Raise
• Fog Creek Compensation
• What Really Happened with Vista
• Short Story – Superiority – by Arthur C. Clarke
• The Myth of Developer Productivity
• The Old Guard
• Cannot Measure Productivity
• Hitting the High Notes
• What if companies interviewed translators the way they interview coders?
• The Unacceptable Persistence of the Digital Divide
• Let’s Talk About Your Plan to Run A Consequence-Free Company
• How Fucked Up is Your Management?
• How to Recruit
• How we pay people at Basecamp
• Basecamp: Our Rituals
• GitHub: Balanced Employee IP Agreement
• So, about this Googler’s manifesto
• So you’re surrounded by idiots. Guess who the real jerk is
• Apache vs Nginx: Practical Considerations

Jan / Feb 2017

• Bring in the Goddamn Adults Already
• The Reality of Developer Burnout
• Effective Product Roadmaps
• Abraham Lincoln’s “Blind Memorandum”
• What I Wish I’d Known About Equity Before Joining A Unicorn
• The Problem With AMP
• Hacking the Army
• Setting Expectations as a Manager
• How to Improve After a Sprint
• Let’s stop calling them ‘soft skills’
• These Are the Most Productive Countries in the World
• Does Unlimited Vacation Time Really Work?

Dec 2016

• A Favor for Your Future Self
• We Need to Talk About Technical Debt
• Accessibility Whack-A-Mole
• How to have an honest one-on-one with an employee

Nov 2016

• The Dirty Dozen Roadmap Roadblocks
• Pay the Price for Open Source
• Video: No one expects the woman code troll – Jenn Schiffer, Engineer/Artist at XOXO Festival
• Redesigning Waxy, 2016 edition
• Quit Social Media. Your Career May Depend on It
• Social Media Is Killing Discourse Because It’s Too Much Like TV
• A look at the impact of inclusive design

Oct 2016

• Contempt Culture
• Field experiment on posting rules in discussions
• Task Performance Indicator: A Management Metric for Customer Experience
• The inaccessible web: how we got into this mess
• Taking PHP seriously
• And it’s gone —The true cost of interruptions
• Your Team In Four Dimensions
• Agile Manifesto
• Writing good code: how to reduce the cognitive load of your code
• Be Careful What You Code For
• My condolences, you’re now the maintainer of a popular open source project
• The way we evaluate developer performance is broken
• Product strategy means saying no

Etcetera

Books I read before I started this list that were particularly formative and that I recommend to any web developer (or manager of them). I’ve resisted linking them to Amazon in the naive hope you might buy them elsewhere.

• Being Geek (Lopp)
• Managing Humans (Lopp)
• Rework (DHH & Fried)
• Remote (DHH & Fried)
• Getting Real (DHH & Fried)
• Designing with Web Standards (Zeldman)
• Don’t Make Me Think (Krugman)
• The Design of Everyday Things (Norman)
• A Book Apart series (several)
• Buzzing Communities (Millington)
• The Indispensable Community (Millington)