Chapter 3. The Itch
My expiration date for a gig has, historically, been three years. Strangely, this mirrors what I believe is the development cycle to get a product right—three releases before it’s real. One release per year, the product is done...and so am I.
I say this like there’s a plan, like I know that after three years it’s time to move on, but this is not a science. This is historic observation. As I look at my resumé, it’s obvious. In fact, I often start leaving before I even notice I’m leaving.
Leaving starts with an itch.
Are You Answering the Phone?
I rarely answer my phone at work. There are really only two types of people who call: lawyers and recruiters. The lawyers are calling for good reason. They know that anything that passes through the keyboard is forever, and since their jobs hinge on conversations that we might not want to be forever, they use the phone.
Recruiters, on the other hand, are just cold calling. They’ve got a name and the main number of your company and they’re dialing. They don’t care who you are—you’re just 10% of your first year’s salary. And they’re the main reason I never pick up my phone.
The phone rings maybe 3–5 times a day. The ringer is low, and 99% of the time I just ignore it, except when I don’t. In the moment of considering the ring, an instant mental analysis occurs that sounds like this: Recruiter. Meh. But I wonder if it’s something interesting? More interesting than what I’m doing right now? More potential? A raise? I could use a raise....
I’m making it sound like this inner dialog is complex and drawn out, but it’s not. It’s a gut check. Am I happy in my job? Yes? OK, ignore the phone. No? Well, let’s see what they have to say.
As I reach over to pick up the phone, a silent alarm goes off in my head because it’s likely I haven’t admitted to myself that there’s a chance I’d consider another gig, but here I am reaching for the phone, picking up, and seeing what the world has to offer.
I’ve never actually ended up in a gig that started with a cold call, but I have ended up in a new gig because a cold call knocked me out of professional lethargy and created a professional itch I needed to scratch.
The Pissed Itch
Before we figure out whether you’re ready for a new gig, let’s first figure out your mindset because it’s going to dictate whether or not we proceed. Are you pissed off at your boss? Did you just get a really bad review? Did you just learn you weren’t included in the next fancy project? Are you seething?
Right, stop reading.
The rest of the chapter assumes you’re in control of your temper and your current gig. You are driving. If you’re pissed, you’re not in the mindset to make solid strategic decisions about your next gig. You’re motivated by a single thought: I. Am. Out of here. There’s a litany of good reasons to be angry with your boss, your company, or your team, but you don’t want to start a job change being pissed off. Nothing taints common sense more than being pissed off.
Early Warning Signs of Doom
Choosing to subject yourself to a recruiting cold call is just one sign that cracks are forming in your job satisfaction. There are others...
Engagement
How engaged are you in your work? I know you love working on that new feature in the product—you’ll always love doing new things—but how about the busy work? How engaged are you in the work that is necessary but tedious? Remember when you joined the company and everyone was bright and you had no clue the boring work was, well, boring? Now that it’s boring, are you able to crank through it, or are you finding excuses to not do it? I’m not talking about a lull of interest; I’m talking about a complete lack of interest in the inane but essential work that moves the company forward.
It’s a warning sign when the onerous busy work drops off my plate. I’m not doing it, because I’ve got a new gig in mind, though I’m months away from that realization. It’s an early sign that the core satisfaction in my job has begun to erode when I’m unable to charge through the work I hate.
Wanderlust
How much are you thinking about your job when you’re not working? When you go to sleep? My question is: how much are you thinking about your job when you don’t have to?
There’s a larger job satisfaction analysis going on inside of wanderlust. In hi-tech, 9 to 5 jobs are dead. I’m a fervent supporter of maintaining a work-life balance that allows you to explore as much of the planet Earth as possible, but I’m also the guy who thinks if you’re going to do this job, you should be absolutely fucking crazy about it. This doesn’t mean that you’re obsessively working 24 hours a day on the product, but it does mean that the work you are doing is part of you.
If your work isn’t finding you in the car or on the bus, if you’re not thinking about the things you build when your mind is wandering, it might be a sign that you’re going through the motions with your work.
Software development is puzzle solving. Given this esoteric set of problems, people, and code, how am I going to build the best possible thing I can? You don’t always solve these problems sitting at your desk. You solve them in the bar, in the shower, in the places you let your mind wander.
If my mind isn’t always passively chewing on the things I need to build, again, it’s a sign that I might not care about what I’m doing.
Whether your engagement is fading or you are lost in wanderlust, both mental states are hurting your current gig more than you think. When your engagement fades, you stop doing busy work. When you are mentally wandering outside of your gig, again, you’re decreasing your daily investment in your gig.
It’s not all bad news. Your big projects are getting attention. The people that stand in your door yelling, they get your cycles, but the quiet work isn’t being touched. A decent percent of the day is busy work, and when you choose to not do that work one day, no one notices, because it’s not high-priority work. When you don’t do that work for three weeks, the busy work becomes an untended garden where the low-priority work slowly grows into reputation-affecting mistakes.
You can go months giving the boring work half of your attention, but it’s just a matter of time before you ignore a task that really matters. Now you’re the person who’s looking for a gig not only because you’re bored, but also because you’re screwing up.
You need to consider your new gig from a place of confidence. You don’t want to be running from a mistake, but walking toward a new opportunity.
The Contradiction List
Before you pick up the phone, before you answer that tempting recruiting email, there are a couple of questions I want you to ask yourself, and then, with these answers in hand, I’ll explain why you should ignore them.
Who are you leaving behind?
I have a Rolodex. It’s not actually a Rolodex, it’s a list, and on that list is every single person whom I’ll call when I do the start-up thing. In each company I’ve worked at, I’ve had the Rolodex moment when I realize that someone I’m working with belongs on this list. It’s a rare, wonderful moment.
There’s a risk when you leave a gig that you’re leaving people behind who you’re going to need at a later date, who aren’t going to survive the transition to your new gig. There’s also a chance that you’ve missed an obvious Rolodex candidate.
The reality is:
Inclusion on the Rolodex is defined by the ability to survive job changes, although, paradoxically, you won’t actually know that for sure until you leave. Part of my inclusion criteria is that I see my relationship with this person as something larger than the current gig. If they’re on the Rolodex, it means I believe our relationship is no longer defined by the current job, and there’s no better way to test this hypothesis than switching gigs.
Are you done?
In your current gig, are you close to a state where all of your major commitments are either complete or won’t come crumbling down if you leave? I’m not saying every single task has been crossed off; I’m saying that the work that you can uniquely do can either be completed or handed off to a competent person. My real question here is: what’s the story that will be told about you when you leave? Will it be, “He’s the guy who bailed when it got tough” or “He left us at a tough time, but left us in good shape”?
The reality is:
You’re never done. There’s never a good time to go. If you’re a key player in the organization, everyone will likely freak out when they hear you’re leaving, meetings will be held to brainstorm backup plans, you’ll leave, and things will pretty much proceed as they did when you were there.
Nature abhors a vacuum, and while your absence will be visually obvious, culturally, one or more people will start jockeying for your gig the moment the departure rumor starts wandering the hallways.
What itch are you trying to scratch?
This is the last question, but it should be first. You’re still reading, so your motivation isn’t “I hate this company.” What is your motivation? You want a raise? That’s great, that’s a place to start, but you know you can get a raise just doing a good job where you’re sitting right now, with people you know, in familiar surroundings. Switching gigs strikes me as a pretty radical change given all you want is more money.
Is your motivation bigger than that? Dumping all your current responsibilities and everyone you professionally know is a shock to the system. You’re in for months of confusion sitting in a place you don’t know with people who speak in strange acronyms. Your motivation around looking for a new gig should be commensurate with the confidence beating you’re about to take.
The reality is:
Take the beating. Every job is a fascinating new collection of people and responsibilities. You need to pay careful attention to whether you’ll fit in to this potential new gig, but even with that due diligence, it’s a crapshoot. You’ll never know exactly what you’ll learn, but I guarantee in the chaotic flurry of new, there is invaluable experience to discover.
Bright and Shiny
Once you have telemetry on the potential new gig, my last question is: “Is it just new or is it unique? And is it progress?”
A new job is not like a new car. The morning after you bought the car, you walk into the garage and think, “Holy shit, a new car. I can’t believe...all the new.” Then, you get in the car and start your drive to work swimming in the new car scent, and halfway to work you realize, hey...it’s just a car.
In analyzing a potential new gig, you need to separate the new from the unique. “What is genuinely unique about this new job?” For me, answers have varied: it’s a start-up, it’s shrink-wrap, it’s not another fucking database product, or it’s a step back, but it’s a company I’ve wanted to work at since I was a kid.
Once you’ve defined what’s unique about the potential gig, you’ve got a bigger question: “Is it what you want to do?” This is the career question. This is when you figure out whether or not you know what you want to be when you grow up.
It’s OK to not have a solid answer to that question. I’m still working on it, but just because you don’t have an answer to a very hard question doesn’t mean you shouldn’t ask it. Does this new gig fit into whatever hazy goals you have for yourself? If you want to be standing in front of a thousand people talking about changing the world, does this gig feel like a step in that direction?
The place to start thinking about a new job, about figuring out what itch you need to scratch, isn’t whether or not you want the job; it’s considering do I know what I want to do?