Chapter 35. A Deliberate Career
I want to hear the story of how you got your first gig in high tech. Like me, you probably did all the things you were supposed to do: you went to the career center, searched the job boards, and attended the career fairs.
It was all vaguely confusing. Nothing was concrete. You threw your pathetic excuse for a resumé to dozens of randomly smiling people and wondered, “Am I ever going to get a job?”
And then it happened. A vacation in Italy. Some bizarre, unimaginable confluence of events that started with you being blind drunk and broke in Florence. You met this guy on the street who was clearly American, you hit it off, and long story short, this chance meeting on the other side of the planet resulted in you getting your first engineering gig at a fashionable start-up in Silicon Valley.
Your thought as you settled into your bright’n’shiny new gig was, “I’ve no control over what is happening to me. I just need to go with the flow, and I’m going to randomly meet someone who is going to randomly believe in me and then money will rain from the sky.”
As an avid fan of instinct, a frequent receiver of random career blessings, and a professional identifier of random opportunity, I understand and have lived this perspective, but hope isn’t going to define your career: you need a strategy.
Three Choices
When I write the word “strategy,” I picture this thick book with a light-blue cover and black binding. The title is My Career Strategy, and below the title in block letters it says “TOP SECRET”. This is not, however, what I mean by having a strategy. I’m talking about a half-hour exercise in thinking about your future.
The only thing I know about your future is that you don’t know what’s going to happen or when. Opportunity is going to show up at the least convenient time, and the moment it arrives, whether you’re ready or not, you’re going to have to make a decision in a moment. Am I going to make a move?
My thought: the more you know what you want, the better decision you’ll make.
I see three big questions you can ask yourself to define a rough strategy for your career. These are questions about your next job, but combined, the answers to these questions will help you understand where you want to go, what you want to build, and how you want to build it throughout your career.
Question #1: Start-up or Established?
Start-up
There is nothing quite like a start-up as an introduction to our industry. If you’re looking for a fire hose full of information pointed straight at your face, I highly recommend the start-up. However, its ability to present you with information is only exceeded by its ability to change that information randomly.
Perhaps the biggest opportunity in the start-up is to build something radically new. That’s why random venture capitalists are throwing money at this no-name group of fine people. They believe that they have a chance to build a thing that has never been built before, and, hopefully, figure out how to make a lot of money from that new thing. The existence of the start-up is a defiant cry that, “Yes, we can do something different,” and that means you are guaranteed to see opportunities and gain experience early in your career that you’re unlikely to see at an established company. It also means you’ll experience an abundance of failure.
During the first Internet bubble, there was only one measure of success. Did you IPO? If you didn’t, you were considered a failure. When the first bubble burst, we discovered there were all sorts of fascinating ways to fail, varying from buy-out to outright take-it-apart-and-fire-everyone failure.
Most start-ups are going to experience some definition of failure, but, well, failure is awesome. I mean it. There’s no experience like the diving saves you’ll perform in an attempt to save your job or your company. It’ll be hell when it’s happening, but when it’s over, you’re going to be the guy who attempted to pull off some amazing professional moves, and these aren’t moves you’ll be asked to perform at a larger company.
The single biggest asset to consider when thinking about joining a start-up is the experience you’ll acquire. If you choose to dream about the millions of dollars you might end up with, I ask that you equally consider the experience of watching your team dismantled as your formerly high-flying company slow runs out of cash and scrambles to restructure itself because three college drop-outs the next town over built your idea better, faster, and cheaper.
Whether your start-up fails or not, the guarantee I make is that you’re going to end up with some amazing stories, and each of those stories will contain a lesson. Sure, these lessons are available at larger companies, but the velocity, intensity, and passion of the start-up will make these stories uniquely yours.
Established
If your average start-up is metaphorically sprinting, your average successful, established company is lumbering along at a comfortable trot. This company believes that it’s running, but it’s not. It ran at some point, became successful and large, and has gently slowed down thanks to its own weight.
This lumbering trot won’t be obvious unless you’ve already experienced the pace of a start-up, and that might be part of the attraction. There’s nothing quite like the calm deliberation of an established company after the frenetic chaos of a start-up, but it comes with a cost.
There’s a constant threat in a start-up, and that’s the threat of failure. You can ignore it when you’re busily working three weekends straight, but it’s always there: “We could fail.” The larger company’s success has hidden this threat under a guise of predictability, domesticity, and sheer momentum. You’ll have fewer responsibilities because there are more of you. The projects will take longer because what’s the hurry? You won’t worry if your paycheck is going to clear, and you’ll bitch when you have to work a few weekends. It sounds kind of sleepy, but there is still much to learn.
Any job, any company, represents a wealth of experience. The risk associated with acquiring that experience at an established company is far less than at a start-up because your larger company has hit its stride. They made it, and one would think they made it because they did something right. The questions are, what did they do right, are they still doing it right, and how is the rightness covering up things they’re doing horribly?
The risk of the established company is that they’ve become used to their lumbering trot. It’s become stable and familiar, and that familiarity defines the entire company’s processes and culture. This is how we do things. This makes their days predictable and measurable. Again, if you’ve been suffering through endless days of risky unpredictability at your last gig, a large company might be the perfect next move.
Question #2: Industry and Brand
The next choice to make is what industry you want to explore. In my career, I’ve been a database guy, a browser guy, a web apps guy, an ecommerce guy, and an operating system guy. If you were to map current industry trends to this career, you’d notice that my career switches followed the bleeding edge. I was at Borland when Windows application development was beginning, and did the same move at Netscape around the emergence of the Internet. All of this varied experience had a point: cross-pollination.
It’s great that you’ve figured out how to get Ruby to scale, and I’m certain you could continue to explore the frontiers of scalable Ruby, but in doing so, there’s a point of diminishing returns regarding your career. It’s comforting to know what you’re talking about and to be recognized by those around you as an expert in whatever it is that you do, but when I stare at a resumé where the past five years have been spent in the same gig, I wonder, “Why hasn’t he gotten bored?”
Granted, your geek instincts and your nerd attention deficiency disorder are likely to continually push you toward the new, so I’m not that worried about you moving on to tackling new technical problems. But while we’re here, I want to talk briefly about brand.
The name, the reputation of a company, is a thing to consider. If you were to tell a complete stranger the name of the company you’re considering, what’s their reaction? Is it well known? Is it viewed as successful? Can they name a product this company produces? This is useful information because when you eventually leave this gig, it’s that name that you’ll be putting on your resumé, and it’s that name that is going to be quickly digested by future employers.
All that said, brand and reputation are not the pivotal decisions in considering a new gig, especially when anonymous start-ups are in the mix. But if you’re considering an unknown quantity in terms of company, try this: describe the opportunity you’re considering. Can you? Something about web services? OK, what about web services? What excites you? What are you going to own? What are you going to build?
Question #3: Management or Development?
There are two career tracks in engineering: development and management. That’s it. As you’re probably already an engineer, this decision is easy to describe but hard to understand: do you want to be a manager?
Why would anyone want to be a manager?
Fact. There is more money to be had in management. This money is a result of more responsibility, and by responsibility, I mean frequent moments when everyone in the room is staring at you, expecting you to make a critical decision on the spot with incomplete information.
Fact. You’ll code less, you’ll work more, and at the end of the day, you won’t be sure you did anything.
Fact. You’ll meet lots more people and be expected to get along with them.
Fact. Much of what you’ve done to be a good engineer isn’t going to apply to being a good manager.
The next two chapters will explore these facts further and go into more detail on the role of management. But the question remains: is this a direction you want to head as part of your next gig? This doesn’t need to be an absolute decision. There are smaller steps you can take toward management. Technical Lead is usually the title for a gig that is a primer for management. Such roles usually have larger decision-making responsibilities without all the bothersome performance reviews, so you can get a feel for wearing a management hat without fully committing.
A Complete Opportunity Move
Here’s a different version of the questions:
Where do I want to go?
What do I want to build?
And how do I want to build it?
As you answer these questions, other smaller questions will pop up that matter specifically to you and that you should also explore. How many people do you want to work with? How much do you want to work? How much responsibility do you want? How much stress can you handle?
Ideally, you should be able to answer these questions independently before you search for your next gig, because the moment a new opportunity presents itself, you’re not thinking about yourself; you’re thinking about the potential new gig. You still need to able to see how this gig fits with your personal strategic direction, as well as answer one more question: what’s the opportunity to grow?
A start-up is more likely to be in a state where it’s hiring lots of people, aggressively attacking new problems, and having a sense of urgency. Still, you can find the same attributes in a large company in a specific group that has been tasked with the new and sexy. This hybrid might be the best of both worlds—the urgency of a start-up supported by the stability of an established company—but is it a fit for you? Does it represent an opportunity you’ve never seen?
At the end of this analysis is an unfortunate truth: you’re not going to know what you’re getting until you’re there. The only guarantee is that it will be different than where you are now, and that means you’re going to learn...something. Good. The more you know, the fewer the surprises.