Chapter 1. How to Win

You’ve had a small number of career-defining moments.

Small decisions cross your desk, your inbox, all day, but this isn’t a small decision. It’s massive, and once you’ve made this decision, there is absolutely no going back. It is in this moment you make a painful discovery—shit, I’m a geek.

You don’t have an MBA. You know there are HR people in the building somewhere, but you’ve no idea what to do with them. You want to hide in the comforting structure of code, but you know that in this moment, this decision is going to significantly affect your career...if only you knew how.

Can I argue for more money after I received an offer? OK, how? Who do I do when my boss lies to me? What do I need to do to resign? What’s a program manager? Should I apply for a management gig? They make more money doing less, right? Can I get a promotion without talking to a single human being? There isn’t a class in college that teaches any of this. Wikipedia can give you definition, but it can’t help a social introvert who sees much of the world through a keyboard.

This is the hand you’ve been dealt. Let’s embrace the geek.

A System Thinker

We’re different, and understanding these differences is a good place to start. At our core, I believe geeks are system thinkers. A simpler way to think about this is that in the mind of a geek, the world is like a computer—discernible, knowable, and finite. After years of successfully using the computer as a means of interacting with the world, we’ve come to follow a certain credo:

We seek definition to understand

the system so that we can discern

the rules so that we

know what to do next so that

we win.

Definition, system, and rules. It all goes back to our ever-favorite tool, the computer. Our success with the computer has tweaked our perspective of the planet. We believe that given enough time and effort, you can totally understand the system. A hard drive has these attributes and make this type of operation faster. More memory will improve these types of operations. When my boss tells me I’m passive-aggressive, I should....

Wait, what? Passive what?

A crisis occurs when a situation appears that doesn’t follow the rules, doesn’t fit in the system, and is inherently indefinable. We go into high alert when we see a flaw in the system because the system is what we tell ourselves to get through the day. Unfortunately, this structure is a comfortable illusion and full of certain flaws that I like to call people.

People Are Messy

People screw things up. They are the sources of bugs. They ask odd questions, and their logic is flawed. In the pleasant mental flowchart we have in our geek heads, it’s a single person who causes us to frustratingly ask, “Who are these people and why the hell don’t they follow the rules? Can’t they see the system? DON’T THEY WANT TO WIN?”

Yes, they do.

No one wants a reminder that life is a crapshoot. That we’re all making it up as we go based on reacting to whatever random strangeness occurs in our corner of the world. The lack of control is especially discomforting to the geek, which is why we construct imaginary structured versions of our world to make the chaos a bit more palatable and predictable.

I’m a geek, and while I’m just as ambiguous and emotionally slippery as that comic book dork in the cube next door, I’ve been staring at geeks struggling with messy parts of high tech for over a decade. I believe I can improve the chances that we can win, even with all these people stumbling around and touching our stuff.

The advice and this book begin with a contradiction: prepare for the unpredictable.

The unpredictable shows up on your doorstep in two forms: simple unpredictability, which you can assess and act on immediately, and world-changing unpredictability that rocks your world and requires serious work on your part. In Being Geek, my hope is to first equip you with a system of improvisation that will help you act on the simple unpredictability and, second, to encourage you to develop a blueprint for your career to prepare for when the sky really falls.

A System of Improvisation

In my head, a handbook is a book with curled pages, a beaten cover, and folded pages that is never far away. It’s achieved this state by being repeatedly and tactically useful. Being Geek’s chapters are structured around a single job. From the initial job search, the interview, the offer negotiations, and learning about your company and your coworkers, to finally deciding it’s time to search for a new gig. The idea is not the arc; the idea is that as you’re going through a small bit of unpredictability, you can flip to Chapter 34 and read about how to interpret your yearly review so you can make a decision: am I or am I not going to get fussy about this poorly written review?

The chapters of Being Geek are standalone, meaning there are minimal threads tying one chapter to the next. This is partially a function of where some of the chapters originated—my weblog, Rands in Repose—but also a function of the geek attention span, which can My hope is these fully contained, easily consumable chapters are useful when small decisions show up, in that they help you take apart your decisions. They aren’t prescriptive, because whatever decisions you have on your plate are yours to make, and the best I can offer is to tell you the story of when I found that decision, what I thought, and how I moved forward.

It’s satisfying: the completion of a task, the making of a decision, getting a thing done. These small bits of motion you apply to your day make up the majority of the decisions you make in your life, and they happen with little pomp and circumstance. Making these decisions and seeing what happens make up the bulk of your experience and how you continue your endless search for rules that define your system. The better you get at them, hopefully, the more success you have and the quicker you make them the next time they show up.

Still, these are the small bits of unpredictability, and you also need to know what to do when the massive unpredictability appears.

A Career Blueprint

You read a book. From beginning to end. While the chapters of Being Geek can stand alone, this book is written around a single hypothetical job and is intended to tell a long story. The time it takes to read this book will, hopefully, give you distance from the day to day work of your job and remind you that you’re working toward something bigger. Your job is not just what you’re doing; it should be preparing you for what you want to do.

As you read this book, you need to keep three classes of questions in your head:

  • What am I doing?

  • What do I do?

  • What matters to me? What do I care about?

Your work day is deviously designed around focusing you on the first question. Think about your state of mind when you get in the car to drive home, when you’re sitting on the subway, when you’re barely pulling yourself out of the sea of things to do. You’re not dreaming about your next gig, you’re not thinking strategically about your career; you are recovering from a day of tactical tasks. That’s what you’re doing, but is that what you do?

Maybe you’re lucky. You’re the software architect. You’re the director of design. You’re the guy who cares more about databases than anything else on the planet Earth. You’ve discovered a larger theme to what you’re doing and that’s what you do. It’s your career, and a career is much bigger than a job.

Perhaps you don’t know. It’s your first gig, and while all this coding is delicious, there sure seem to be a lot of people running around talking about career growth. That’s what HR is going to do for me, right? My boss has that covered, right?


As an avid watcher of management in the Silicon Valley for coming up on two decades, I can safely say that the good intentions of HR and partial attention of your boss does not a career make.

Whether you know what you do or you don’t, the act of reading this book from cover to cover is a few hours of your time when you get to ask, “What matters to me? What do I care about?” Does this management gig float my boat? Am I developer for life? Is the fact I spend the entire subway trip home cursing my gig a bad sign? It’s professionally fashionable to bitch about your company and your inept manager, but when you start bitching about your career, I call bullshit. The idea that anyone besides you is responsible for your career is flawed. Your boss is only your boss while he’s your boss. Your career is yours forever.

You choose your career and the choice makes life easy when massive unpredictability arrives. Think about it like this: how much easier would it be to make that big decision if you knew exactly what you wanted to do? Is it easier or harder to argue for that new project at work when you know it’s perfect for your career goals? How would the review conversation go with your boss when you’re completely sure that you want to get into management?

All decisions are easier when you’re clear where you’re headed.

A Collection of Moments

Your career is a collection of moments when you make a decision. PC or Mac? Answering that recruiting email or not? Confront or retreat? Even with this book in hand, you’re going to screw up as many decisions as you make correctly, which is a troubling thought for the system-searching geek who is simply trying to win, but there are still rules to discern.

With time and experience, you’ll learn there is a finite set of personalities walking the halls. Yes, they have their individual nuances, but these personalities and their motivations can be understood. Your boss and his motivation will vary from company to company, but it’s a knowable set of motivations varying somewhere from “hiding until I retire” to “driving everyone absolutely crazy as I attempt to conquer the world.” You can make most meetings useful. You can dig yourself out from underneath the endless list of things to do. It’s OK to quit a job with people you like because there are a lot of people to like out there.

Being Geek is a distillation of 15 years in the Silicon Valley working at companies both large and small. I’ve had equal parts of calm and chaos, and I’ve been keeping notes during the entire time because I believe I’m always one rule away from figuring it all out, and that’s how you win.

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