In the heart of software development lies “the system”. The system is always complicated enough that you cannot fully grasp it and it is built by stacking parts on top of another that are just a tad too big to be called simple. The life of a software developer is an ongoing series of isolated projects that are at the threshold of his or her capabilities. We call these projects “epics”, “stories” or just “issues”. The sum of these projects is a system.
Don’t get me wrong – there a tons of issues that just require an hour, a cup of coffee and a few lines of code. This is the green zone of software development. You cannot possibly fail these issues. If you require twice the time, it’s still way before lunchtime. And even if you fail them, a colleague will have your back.
I’m talking about those issues that appear on your to-do list and behave like roadblocks. You dread them from far away and you know that this isn’t smooth sailing for an hour, this will be tough work for several days. This isn’t just an issue, it is an issue by itself for you. You are definitely unsure if you can make it.
Typical small project management
How do you approach such a project? It isn’t an issue anymore, as soon as you get emotionally involved, it becomes a project. Even if your emotion is just dread or fear, it is still involvement. Even if your management style is evasion, it is still project management. Sure, you can reassign a few of these icebergs, but they will always be there. You need to learn to navigate and to tackle them. Hitting an iceberg in the “frontal collision”-style isn’t a good idea.
On closer inspection, every project consists of numerous parts that you already know a solution for – typical one-hour issues – and just a few parts that you cannot estimate because you don’t know how to even start. Many developers in this situation take the route of least resistance and start with the known pieces. It’s obvious, it feels good (you are making good progress, after all!) and it defers failure into an uncertain future (aka next work week). Right now, the project is under control and on its way. We can report 8
0% finished because we’ve done all the known parts. How hard can the unknown parts be anyway? Until they strike hard and wreck your estimates with “unforeseen challenges” and “sudden hardships”. At least this is what you tell your manager.
Risk first!
My preferred way to approach those projects is to reveal the whole map, to estimate all parts before I delve into the details. I already know most of the easy parts, but what about the unknown and/or hard parts? I don’t know their solution so I cannot reliably estimate their size. So I sit down and try to extract the core problem that I don’t know how to solve yet. This is the thing that prohibits an estimate. This is the white area on my map. This is the “here be dragons” area. If I spend my resources doing all the work other than this, I will succeed until I stand on the border of this area and see the dragon. And I will not have sufficient resources left. My allies (like my manager and colleagues) will grow weary. I will have to fight my hardest battle in the most inconvenient setting.
My approach is to take the risk upfront. Tackle the core problem and fail. Get up and tackle it again. Fail once more. And again. If you succeed with your task, the war is won. Your project will still require work, but it’s the easy kind of work (“just work”). You can estimate the remaining tasks and even if you’ve overspent in your first battle, you reliably know how much more resources you will need.
Fail fast
And if you don’t succeed? Well, then you know it with the least damage done. Your project will enter crisis mode, but in a position when there is still time and resources left. This is the concept of “fail fast”. To be able to fail fast, you need choose the “risk first” approach of task selection. To tackle the risk first, you need to be able to quantify the “risk” of your upcoming work.
Assessing risk
There are whole books about risk assessment that are interesting and helpful, but as a starter, you only need to listen to your stomach. If your stomach tells you that you are unsure about a specific part of your project, put that part on the “risky” list. If you don’t have a reliable stomach, try to estimate the part’s size. Do the estimation game with your colleagues. Planning poker, for example, is a great tool to uncover uncertainty because the estimates will differ. Just remember: Risk isn’t correlated with size. Just because a part is big doesn’t mean it is risky, too. Your crucial part can maybe be developed in an hour or two, given an inspiration and a cup of coffee.
Failing late means you’re out of options. Failing fast means you’ve eliminated an option and moved on.

If we were to choose the holy book of software development, we probably couldn’t agree on one or even a dozen titles. And that is a good thing, because there is no one true way of software development. Clean Code by Robert C. Martin would maybe show up in the late contenders. But if we were to choose the most preachy book of software development, well, I have a favorite. This book is so loud that you cannot ignore it. And it is so opinionated that you’re either nodding your head like a heavy metal fan or writhing in averseness. That’s a good thing, too. Because it forces you to think. Your immediate emotional answer needs support by rational arguments and this book will provide you with ample opportunity to gather arguments for your consent or rejection. What this book probably won’t do is leave you unaffected. When it came out in 2008, it was an instant classic. You could spice up any gathering of software developers by making a statement about this book, be it pro or contra. And even today, ten years later, I would say that even if the loudness is deafening, the clarity of the messages makes this book a worthwhile read for every software developer. My grief with it is foremost that for a book called “Clean Code”, some examples of actual code are quite dirty or even plain wrong. Read it with an active mind and it will be a cornerstone of your professional career. But be careful, it seems that currently printed instances have physical quality problems.
Ever since Extreme Programming hit the (european) scene in 1999, I was curious about Test Driven Development (TDD). I tried automated testing and unit tests whenever I could, read books and later watched videos about the topic. But I never grokked it. It just didn’t work for me and I didn’t even know why. My most feared trap was the one-two-everything syndrome, where you write two simple tests and then have to implement the whole algorithm to fulfill the third test. It was always the third test that broke my rhythm. I tried to exchange experience with TDD practitioners, but their own examples were mostly trivial and my examples always led nowhere (for reference: Try a simple Game of Life in TDD style). I felt dumb and inadequate. When Robert C. Martin (the author of Clean Code) told the developer world that you are either “TDD or not professional” (read
Some years after the GOOS experience, another summer beach holiday was due and as usual, I included a software development book in my luggage. “Domain Driven Design” by Eric Evans came out in 2003 and was praised by some and ignored by most, including me. It took me ten years to finally read it and when I did, it hit me hard. Since my early days as a programmer, I tried to build a meaningful data model with actual types for each program I developed. But it occurred to me that I did it half-heartedly all the time. It shouldn’t stop at a data model, it should be a complete domain model. And for that to work, you need to grok the domain. I review a lot of my code before that insight and always find it funny how I invested effort in my models but more often than not stayed in the technical realm. I cannot say that my programming has changed much from the book, as most concepts meandered through the community since 2003 and were picked up by me mostly under different names. But my software development approach has changed dramatically. I don’t start my thinking from the technical side anymore. And that helps with “business alignment” and all the other magic words that finally have real tangible benefit. And I can now pinpoint when that alignment loosens and employ counter-measures instead of ending up in a special case hell. The best thing was that this book doesn’t require a laptop so I got to sit on the beach that summer with the book in my hands and my head in the clouds. It might be old, but it’s still gold.
I anxiously waited for this book to be printed. Not because I pre-ordered, but because I held talks, workshops and lectures about the topic before the book was available. And I wanted to make sure that I’m not telling nonsense. But Robert C. Martin took his time and delayed the deadline month after month. Then, nearly a year later, the book reached the stores in late 2017. So I would have to wait for my winter holiday to read it. I couldn’t wait and began right away. The book is a slow burner and feels like a long introduction. By the time the central proposition is revealed (and yes, it reads like good unagitated spy thriller at times), you’ve probably already figured it out yourself. And that’s a good thing in my mind, because it feels as if it was your idea and Uncle Bob is just there to nod and congratulate you for your intellect. This book is so many times less preachy than “Clean Code”. If we compare spy thriller literature, this is a John le Carré while Clean Code would be an Ian Fleming (James Bond). “Clean Architecture” is not about programming, it talks about software architecture, a topic that I missed greatly in my early developer years. I liked this book so much
All the other books talk about different aspects of programming, software development or related technical topics. But what about a book that raises a simple question: “Why is IT technology so complicated?”. And gives the answer: “Because we want it this way.”. That’s actually true. In a world without most of the restrictions of the physical world, we were unable to build solutions that actually helped us and came up with machines and software that overwhelmed most people. It needed a whole new generation of “digital natives” until concepts like internal operation modes (e.g. insert vs. overwrite) were intuitively understood. Not because they became simpler, we were just used to the complexity. Alan Cooper described the problem and gave at least hints for solutions in 1999, nearly 20 years ago. That’s the timespan of a generation. This book made me think hard about the status quo I silently had accepted with technology. It just was like it was, what else could there be? If I reveal a tiny bit of different approaches I can think of now, I’m often confronted with incomprehension. Not because I’m particularly clever and everyone else is dumb, but because there seems to be no problem if you’ve grown accustomed to it. If you want to see some of the pain other (older) people feel when interacting with technology and software, read this book. It is an eye-opener to common problems no software developer ever had. It is the first step into the world of UX (user experience), where it’s not as important if the developer feels alright but if the user feels at least adequate. It might be a classic and feel a bit outdated and weak on the solution side, but to understand the problem properly is the first step to appreciate possible answers. And Alan Cooper didn’t stop there. Read his
More by chance, my co-founder stumbled upon “
In 2004, Michael Feathers wrote a book that contains his 20+ years of experience with software development and named it “
Martin Fowler was a very productive author in the late nineties. I’ve read most of his books from this period, if maybe with a few years delay. “
Since the late 80’s, Tom DeMarco and Timothy Lister wrote one book after the other. Each book describes a common business-oriented problem and at least one working solution for it. And yet, the very same problems still persist in the business world. It’s as if nobody reads books. “