The Library Link to heading

I tend to think of books as long-form conversations. Someone invested time and effort to write about something they care about, and I chose to spend time with their thoughts on the topic. Some of the books below sharpened how I reason about systems, others about failure, risk, or how groups of people actually work under pressure.

This page is a curated subset of books that influenced how I think and work. It is intentionally incomplete and biased toward works I still reference mentally, if not explicitly.

The books are grouped by how I use them, not by genre. Inclusion in this list does not imply agreement with everything in a given book, just that I continue to find them useful.

Systems & Architecture Link to heading

Books that shaped how I think about complexity, trade-offs, and long-lived systems.

  • Designing Data-Intensive Applications — Martin Kleppmann
  • Patterns of Enterprise Application Architecture — Martin Fowler
  • Software Architecture: The Hard Parts — Neal Ford et al.
  • Operating Systems: Internals and Design Principles - William Stallings
  • Clean Architecture — Robert C. Martin

Reliability, Failure & Risk Link to heading

How systems fail — technically and socially — and what that implies for design and operations.

  • Site Reliability Engineering — Betsy Beyer et al.
  • Building Secure and Reliable Systems — Heather Adkins et al.
  • The Field Guide to Understanding “Human Error” — Sidney Dekker
  • The Checklist Manifesto — Atul Gawande
  • Beyond the Goal — Eliyahu M. Goldratt

Security & Adversarial Thinking Link to heading

Security as a sociotechnical problem, not a checklist.

  • Beyond Fear — Bruce Schneier
  • The Cuckoo’s Egg — Cliff Stoll
  • Security Engineering - Ross Anderson
  • Agile Application Security — Laura Bell et al.
  • Crafting the InfoSec Playbook — Jeff Bollinger et al.

Software Engineering Practice Link to heading

How code is written, tested, maintained, and understood over time.

  • Software Engineering at Google — Titus Winters et al.
  • Working Effectively with Legacy Code — Michael C. Feathers
  • Domain Driven Design - Eric Evans
  • The Pragmatic Programmer — Andrew Hunt, David Thomas
  • Why Programs Fail - Andreas Zeller

AI & Machine Learning Systems Link to heading

How machine learning and language models behave as production systems, and how they affect system boundaries, reliability, and decision-making.

  • Designing Machine Learning Systems — Chip Huyen
  • AI Engineering — Chip Huyen
  • Building LLMs for Production — Louis-François Bouchard, Louie Peters

Organizations, Leadership & Work Link to heading

How people coordinate, decide, and sustain performance.

  • Staff Engineer — Will Larson
  • The Manager’s Path — Camille Fournier
  • The Fearless Organization — Amy C. Edmondson
  • The Goal — Eliyahu M. Goldratt
  • Lean from the Trenches — Henrik Kniberg

Analysis, Decision-Making & Context Link to heading

Books that influenced how I evaluate information, uncertainty, and second-order effects.

  • Structured Analytic Techniques — Richards J. Heuer Jr., Randolph Pherson
  • Cases in Intelligence Analysis — Sarah Miller Beebe, Randolph Pherson
  • Naked Statistics — Charles Wheelan
  • Talking to Strangers — Malcolm Gladwell

I tend to return to a small number of these books repeatedly. Most influence comes less from reading than from revisiting ideas when context changes.