100 Books Like Managing Chaos

It is through Brené Brown’s words in this book that I began to make sense of my journey, which is marked by loss, resilience, and an unwavering search for belonging. As I navigated the often-turbulent waters of corporate life, I wrestled with a deep-seated issue, a trait so common among my fellow Gen Xers: the struggle with authority. Through this book, it is evident that attempting to fit in, to mold myself into the expectations of others, often leads me to more heartache than success.

My path has been riddled with tremendous trials designed to dampen my spirit. Yet, through them, I have found strength. I appreciate the depth of resilience that Brené Brown speaks about. In this digital age, I often reflect on my past before the existence of social media, the simplicity of outdoor moments when I was young, and face-to-face conversations that now seem increasingly rare. I… show more.

A mental model is our unique map of all our knowledge. Each person has their own, and we can’t see each other’s mental models or even see our own. Yet those maps dictate everything about how we show up and how we interpret the world around us. 

Mental Models by Indi Young is the best deep dive into this subject and stands as a must-read for anyone making things for other humans to make sense of. If you are going to succeed in practicing information architecture, you must become increasingly adept at understanding how other people think about the world. 

I recommend this book because it takes something theoretical and presents a solid methodological approach that anyone can grasp and adapt to their process as long as they are curious. This book also served as a major inspiration when writing How to Make Sense of Any Mess, as it… show more.

Living in Information by Jorge Arango introduces information-soaked individuals to an easy-to-grasp architectural vocabulary that describes the patterns and shifts of context in the digital (and increasingly the digitally-enhanced-physical) world.

I recommend this book as a map of the territory when it comes to designing with or for digital systems and experiences. Jorge is a wonderful storyteller as well as a crystal clear communicator and this book is a jewel on my sensemaking bookshelf.

Jorge is also one of my favorite authors to keep up with regarding information architecture. His podcast and blog are worth a follow should the subject of his book perk your interest.

Liminal Thinking by Dave Gray provides a solid roadmap to help navigate through the rocky terrain of understanding and being able to change your own mind and habits.

When I first read this book, the words mind-blown could not quite cover it. I was in fact completely devastated by the truth that I learned in this book. It taught me the danger of making sense of messes while on autopilot and the power of the present moment as a forcing function in my work. ‘Liminal’ is a word I had to look up the first time I heard it, but it has since become the go-to word I use to describe those hard and squishy times when I am still making the decision about how to show up in the world. 

I recommend this book because as Dave Gray writes “Beliefs form the basis of everything people say,… show more.

This is a book for practitioners, by a practitioner, full of practical learnings that I was able to start using in my work immediately.

I especially appreciated the parts teaching the core principles of infrastructure as code (e.g., systems are disposable, consistent, can easily be reproduced, etc.), core practices of infrastructure as code (e.g., use definition files, self-documented systems and processes, version all the things, etc.), and the idea of antifragile systems (rather than just systems that you prevent from breaking) and autonomic systems (rather than just automated systems).

This book felt like a chance to sit with a few experienced Ops people and hear their war stories.

The book is full of concrete, actionable learnings that are essential for running software, including operational requirements (e.g., configuration, draining, hot swaps, feature toggles, graceful degradation, etc.), software architecture (e.g., three-tier web service, four-tier web service, load balancing models etc.), scaling patterns (e.g., horizontal duplication, service splits, caching, etc.), resiliency patterns (software vs hardware resiliency, spare capacity, failure domains, etc.), and much more.

I loved being able to pick up decades of experience and hard-won knowledge by just flipping through a few pages of a book! 

When I worked in application security at Microsoft, we still had products that shipped every few years. I learned to scale application security in that world, but many people live in a different world now. AAS helped me understand which of our approaches translated well, which had to be transformed, and which needed to be discarded or replaced. I regularly refer back to it, even a few years later.

One of the best ways to understand how software works is to study how it fails. When I was just starting my career in software security, I read this book to learn about binary exploits like buffer overflows. It’s been a long time since I’ve written a binary exploit, but digging into the nitty-gritty, low-level details of how software runs on a real system has helped with everything I’ve done as an engineer since.

A lot has changed since this book was published in 2008 (and running the accompanying Live CD has gotten trickier), but the fundamental concepts are as relevant as ever.

This book is set in the same universe as The Phoenix Project and The Unicorn Project, but it's at a new company named investments unlimited.

It's also a fictitious story, but with all brand new characters, and brand new problems! In this book they cover security much more deeply than any of the other previous books, talking about how compliance and audit can work together with the information security and DevOps teams.

They talk about common problems that I have faced in many organizations, and a lot of the stories feel so familiar I wonder if the authors have followed me around throughout my career.

Although of course they save the day in the end, there are many parts of the book where we're not quite sure if they're going to make it or not with various characters learning to see things in new ways, so that they can make… show more.

This book is one of the first comprehensive accounts of the ways that code and algorithm design have transformed our society. While reading this book, I also learned about the complex legal battle in which large corporations push forward their commercial interests through their code.

Using copyright laws and with the support of governments, big tech companies have successfully managed to dominate our social and cultural spheres, making it more difficult for smaller companies and individual users to raise their unique voices. What I also like about this book is that it offers practical solutions and directions to fight back and make this world more equal.