Greenfield vs brownfield: working with messy legacy systems

Special thanks to John Allspaw, Sheeri Cabral, Martin Smith, and David Woods for joining us!

Ben Affleck’s been making the promo rounds, but the specific convo we reference is recapped here: https://www.moviemaker.com/ben-affleck-ai-explains/

The Messy 9 are:

congestion

cascade

conflict

lag

saturation

friction

tempo

surprise

tangles

Dave’s been doing a set of videos on Resilience Engineering, some of which have some crossover with the Messy 9 - you can find the first one here:

https://resiliencefoundations.github.io/video-1-introduction-pt-1-it's-all-about-viability.html

Previous TiF episode on the messy 9:

https://www.thisisfinepod.com/the-pod/complex-systems-and-the-messy-nine-wspecial-guests-dave-woods-and-john-allspaw

Richard Cook on Above the Line/Below the Line: 

Written - https://dl.acm.org/doi/pdf/10.1145/3379510

A good excerpt from a talk from John Allspaw on Above the Line/Below the Line: https://www.youtube.com/watch?v=8bxj-FLEi10&list=PLb1aZTnPf3-OMChMkrr6WsokRI6LOnuem

Colette mentioned the competence knowledge model: https://en.wikipedia.org/wiki/Four_stages_of_competence

There’s a good argument based on the conversation here that AI makes it harder for Consciously Incompetent people to graduate to Conscious Competence. And, in Martin’s case, it makes Unconsciously Competent folks need to backtrack into Conscience Competence to “teach” it how to do things they don’t always think about.

We can reset the clock to 0 episodes since we’ve mentioned the Ironies of Automation: https://ckrybus.com/static/papers/Bainbridge_1983_Automatica.pdf

There is a good blog on Jamie Zawinski’s saying on regular expressions here: https://regex.info/blog/2006-09-15/247

Alex Gorbachev and The Battle Against Any Guess seems to have become a paper https://www.researchgate.net/publication/251255185_Battle_Against_Any_Guess

Dave talks about Robust Yet Fragile as part of Resilience Engineering here: https://www.youtube.com/watch?v=gFotUdLL2zs

Lorin Hochstein’s blog post that Dave is referencing is https://surfingcomplexity.blog/2026/01/19/amdahl-gustafson-coding-agents-and-you/

Fred writes a good one on the Law of Stretched Systems: ​​https://ferd.ca/the-law-of-stretched-cognitive-systems.html

The 1985 paper Dave keeps mentioning could be any number of things he released that year, but I have a hunch it’s this one: https://ojs.aaai.org/aimagazine/index.php/aimagazine/article/view/511 or this one: https://link.springer.com/chapter/10.1007/978-3-642-50329-0_11

Dave references a lot of things around the economic sustainability around AI, and Ed Zitron has been writing quite a bit about that for the last year and change. See: https://www.wheresyoured.at/wheres-the-money/

https://www.wheresyoured.at/big-tech-2tr/

Among others.