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Ask Dr. Web with Jeffrey Zeldman

If Ever I Should Leave You: Job Hunting For Web Designers and Developers

A note from the editors: During the 1990s, “Ask Dr. Web” was a regular part of Zeldman.com—and now Dr. Web is back to answer your career and industry questions. Read on for his advice, learn the story behind the column, and don't forget to ask a question of your own.

In our last installment, we discussed what to do when your boss is satisfied with third-party code that would make Stalin yak. This time out, we’ll discuss when, why, and how to quit your job.

When is the right time to leave your first job for something new? How do you know you’re ready to take the plunge?
Wet Behind The Ears
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Dear Wet Behind:

From frying an egg to proposing marriage, you can never know for sure when it’s the right time to do anything—let alone anything as momentous as leaving your first job. First, search your heart: most times, you already know what you want to do. (Hint: if you’re thinking about leaving your job, you probably want to.) This doesn’t mean you should heedlessly stomp off to do what you want. Other factors must be carefully considered. But knowing what your heart wants is vital to framing a question that will provide your best answer.

So ask yourself, do I want to leave? And if the answer is yes, ask yourself why. Are you the only girl in a boys’ club? Perhaps the only one with a real passion for the web? Are other folks, including your boss, dialing it in? Have you lost your passion for the work? Are you dialing it in? Is the place you work political? Do your coworkers or boss undervalue you? Have you been there two years or more without a raise or a promotion? Most vital of all, are you still learning on the job?

Stagnation is fine for some jobs—when I was a dishwasher at The Earth Kitchen vegetarian restaurant, I enjoyed shutting off my brain and focusing on the rhythmic scrubbing of burnt pans, the slosh and swirl of peas and carrots in a soapy drain—but professionals, particularly web professionals, are either learning and growing or, like the love between Annie Hall and Alvy Singer, becoming a dead shark. If you’ve stopped learning on the job, it’s past time to look around.

Likewise for situations where you face on-the-job discrimination. Or where you’re the only one who cares about designing and building sites and applications that meet real human needs, and of which you can truly be proud. Or where, after three years of taking on senior-level tasks, and making mature decisions that helped the company, you’re still seen as entry-level because you came in as an intern—and first impressions are forever. Or where you will never be promoted, because the person above you is young, healthy, adored by the owner, or has burrowed in like a tick.

Some companies are smart enough to promote from within. These are the companies that tend to give you an annual professional development budget to attend conferences, buy books, or take classes; that encourage you to blog and attend meet-ups. Companies that ignore or actively discourage your professional growth are not places where you will succeed. (And in most cases, they won’t do that well themselves—although some bad places do attain a kind of financial success by taking on the same kinds of boring jobs over and over again, and hiring employees they can treat as chattel. But that ain’t you, babe.)

It’s important, when answering these questions about your organization and your place within it, to be ruthlessly honest with yourself. If you work alongside a friend whose judgement you trust, ask her what she thinks. It is all too easy, as fallible human beings, to believe that we should be promoted before we may actually be ready; to think that people are treating us unfairly when they may actually be supporting and mentoring us; to ignore valuable knowledge we pick up on the job because we think we should be learning something different.

If there’s no one at your workplace you can trust with these questions, talk to a solid friend, sibling, or love partner—one who is brave enough to tell you what you need to hear. Or check in with a professional—be they a recruiter, job counselor, yoga instructor, barista, or therapist. But be careful not to confide in someone who may have a vested interest in betraying your confidence. (For example, a recruiter who earns $100,000 per year in commissions from your company may not be the best person to talk to about your sense that said company grossly undervalues you.)

Assuming you have legitimate reasons to move on, it’s time to consider those other factors: namely, have you identified the right place to move on to? And have you protected yourself and your family by setting aside a small financial cushion (at least three months’ rent in the bank) and lining up a freelance gig?

Don’t just make a move to make a move—that’s how careers die. Identify the characteristics of the kind of place you want to work for. What kind of work do they do? If they are agencies, what do their former customers say about them? If friends work for them, what do they say about the place? What’s their company culture like? Do they boast a diverse workforce—diverse psychologically, creatively, and politically as well as physically? Is there a sameness to the kind of person they hire, and if so, will you fit in or be uncomfortable? If you’d be comfortable, might you be too comfortable (i.e. not learning anything new)? Human factors are every bit as important as the work, and, career-wise, more important than the money.

If five of your friends work for your current employer’s biggest competitor, don’t assume you can walk across the street and interview with that competitor. The competitor may feel honor-bound to tell your boss how unhappy you are—and that won’t do you any good. Your boss might also feel personally betrayed if you take a job with her biggest competitor, and that might be burning a bridge.

Don’t burn any bridges you don’t have to. After all, you never know who you might work for—or who you might want to hire—five years from now. Leaving on good terms is as important as securing the right next job. Word of mouth is everything in this business, and one powerful enemy can really hurt your career. More importantly, regardless of what they can do for or against your career, it’s always best to avoid hurting others when possible. After all, everyone you meet is fighting their own hard battle, so why add to their burdens?

This isn’t to say you don’t have the right to work for anyone you choose who chooses you back. You absolutely have the right. Just be smart and empathetic about it.

In some places, with some bosses, you can honestly say you’re looking for a new job, and the boss will not only understand, she’ll actually recommend you for a good job elsewhere. But that saintly a boss is rare—and if you work for one, are you sure you want to quit? Most bosses, however professional they may be, take it personally when you leave. So be discreet while job hunting. Once you decide to take a new job, let your boss know well ahead of time, and be honest but helpful if they ask why you’re leaving—share reasons that are true and actionable and that, if listened to, could improve the company you’re leaving.

Lastly, before job hunting, line up those three months’ rent and that freelance gig. This protects you and your family if you work for a vindictive boss who fires employees he finds out are seeking outside jobs. Besides, having cash in the bank and a freelance creative challenge will boost your confidence and self-esteem, helping you do better in interviews.

A good job is like a good friend. But people grow and change, and sometimes even the best of friends must part. Knowing when to make your move will keep you ahead of the curve—and the axe. Happy hunting!

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