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

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.

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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

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!

17 Reader Comments

  1. I feel like I am getting stagnant at my current job, though ideally I would prefer conditions to change here rather than looking for a position elsewhere. I was hired on by my employer with the promise that this would be a position with much growth opportunity and that I would help build a design team. It’s now been over 2 years and I’m still the only designer here. Our development team has grown but when I mention how it would be great for us to hire a new designer, they propose having someone overseas do some design work. That is not ideal so I usually will do what it takes to never outsource design like that. How can I best convince them that we need to hire more talent in-house? I love our development team but I miss having designers around me to brainstorm and collaborate with. I hope the only way to do this isn’t to threaten leaving for another offer.

  2. So the majority of those reasons up there are things I’m dealing with now and why I’m currently searching, but amongst all the rosy “It’s a great time to be a designer” talks and assertions that there are thousands of designer openings available, 3-4 months into my job search and I’ve come away with nothing but spent vacation & personal days on disappointment after disappointment…furthest I got was a second interview that afterwards the organization changed their mind on the opening and are “reassessing”. If that’s code for “Nobody, including that last guy, are any good”, I don’t know, either these jobs aren’t nearly as numerous as reported and/or the requirements are obscene and only for those who’ve had the privilege (yes that p word) or luck of getting good gigs.

    I don’t know anymore, maybe I should just be happy with where I’m at and that I have a job, even if it is far less than ideal (this is obviously an understatement but I do not have the energy nor inclination to air dirty laundry). I’ve done the learn to code thing. I got front-end, visual, and UI layout with responsive chops, preprocessors, writing markup from scratch, etc., but in the push to burn our selves out even faster, I guess these aren’t enough and I need to keep grinding out new portfolio work until I wave my 30s goodbye. ¯_(ツ)_/¯

  3. Alyssa:

    Your story feels familiar to me. I’ve come on board jobs that promised me one thing but, even after several years, weren’t able to deliver it. Sometimes the people making the promise know they won’t be able to deliver on it, and are offering a nonexistent carrot merely to get you to say yes. Those are no-win situations, and if step in one, your only recourse is to find a better job elsewhere.

    But it doesn’t sound like that’s the case here. Based on your attitude toward them, and your desire not to seek work outside your current position, it sounds like the folks who hired you sincerely believed they’d be able to offer you growth and opportunity. And you’re responding to their decency and honesty with loyalty and extremely hard work. That’s commendable. You sound like a terrific employee.

    Unfortunately, though, the growth opportunities you were promised aren’t happening for you. And it sounds like, even if your employers meant well initially, they are now taking advantage of you.

    Outsourcing additional design work overseas, although it is being offered as a way to relieve you of some tasks, won’t bring you the professional growth you’d experience if your employers brought in another designer to work at your side. It may also be a sign that your employer doesn’t totally value design, since they believe design can be outsourced effectively to someone with whom none of you has much or even any real contact.

    I may be reading too much into this, but it’s easy to envision this offer to outsource design work as a subtle threat to your security, to which you respond by doing lots of extra work without complaint. Even if I’m wrong, and your employers are wonderful people who value you and understand the value of design, it doesn’t sound like they have the budget, or the willingness, to create the environment you need to take your career to the next level.

    If you were two years away from retirement, it may be worth putting up with on-the-job stagnancy. But that’s not you. Your career matters, and even if your employers are the nicest folks on earth, it sounds like you owe it to yourself to start looking around.

    Thanks for sharing and hope this helps!

  4. Scott:

    I hear you and feel for you. Please don’t let the challenges discourage you. And—don’t hate me for saying this—please try to enjoy the journey. I know that sounds absurdly hippie-dippy and a bit ridiculous, especially when you’re beginning to feel discouraged. But keeping a positive attitude, however difficult that may be at times, will help you do better in interviews. It will also help you spot opportunities you might miss if you lose heart.

    The next right job may take a little longer to find, but that’s okay. You’re a rare and special person, looking for a rare and special gig, and those don’t grow on trees. The time you’re putting in now will lead to the result you seek if you stay patiently focused and positive. Don’t let negative and noncommittal people make you lose heart!

    Reading between the lines of your last paragraph, I also wonder if you’re spreading yourself too thin. Doing the “learn to code thing” and acquiring all the other skills you’re describing is great in so far as it provides you with a solid background that will enable you to collaborate better with others, and even fill in for them when needed—for instance, if your coder gets sick the night before a launch. But you might also be losing focus, or presenting yourself as someone who isn’t quite sure what he wants to do. I haven’t seen you interview and I may be completely off-base. If so, please ignore this paragraph (and know that it comes from a supportive place, even if I am misguided).

    But if I am right, you *might* be sending signals of which you’re unaware—signals potential employers misread as “Scott isn’t sure what he wants to do” or “Scott feels overwhelmed.” Again, if this is happening—and it may very well NOT be; I don’t know you, sir. But if it *is* happening, now’s your chance to do a quick, subtle course correction.

    Maybe what you need to do is focus, not on all the things you *can* do, but on the one thing you really want to do. Your passion for a specialization may be exactly what the *right* employer is looking for. She or he is out there. Good luck and keep us posted!

  5. I should have read this 3 months ago before I quit my job. All the reasons to quit that you mentioned in the article? That’s how I felt.

    I’ve still got no job until now. I admit that I wasn’t prepared to lose it. It was a big mistake on my part but what I can only do now is to stand up back again and try harder.

    Even though this was late, it was still a great read and I realized my mistakes. Thanks.

  6. @dinobot13: Glad to hear you’ve landed back on your feet. Congratulations on the new job. And, hey—the only reason I know these things is because I’ve made dozens of terrible mistakes in my career. Everybody should have the opportunity to make mistakes! 🙂

  7. I read this at the perfect time, my case as grown a little personal with my boss now, no promotion five years down the road, my passion to code for them is more than abused, my advice hardly counts to them, after mistakes are done outside my line of advice, it then flies back to me in fury. i can hardly explain myself here, I would need like a thousand pages I think, I just feel like I hardly matter any more despite my input for all those years, am still told phrases like “I should know who the boss is”, just because I disagree with certain decisions they make in my field, I feel like a puppet doing wrong things just because my boss insists, my options are an exit plan and this came in time with the best advice, thanks

  8. I’m writing this as today is my last day at this company I worked at for one and half + years, and I am quite happy I’m leaving. Very happy.

    Why did I leave? For the reasons mentioned above by Mr. Zeldman and what most people here have said.

    I got fed up with the incompetence, big egos and lack of respect. Besides, I wasn’t learning anything anymore. I became a tool to solve their JIRA tickets. Yeah. Lame.

    I was thinking for a while to leave, but I hadn’t found where to go to. Then, after a project where the developer had no idea about SVGs, I got heat from my manager for wanting to use “new technologies”, and emailed me this jewel: …and ultimately the copy and design decisions are mine – not yours.

    LOL. RE-LOL.

    With a shitload of years in the visual design and web design fields, I immediately knew I had to leave and take my knowledge somewhere else. Again.

    So I listened to my heart and turned my 2 weeks notice the following morning. Bam!

    And no, I still haven’t found another job… but I don’t care.

    This isn’t the first time I have left a job without having another one lined up. It’s the 3rd.

    Of course I have finances planned for some time and all that stuff, but my circumstances are likely different from someone else’s.

    But that’s not my point. My point is: Peace of mind is PRICELESS.

    I have found that trying to find a job while at another job can be difficult and stressful because you have to lie left and right, use sick and vacation days to go to interviews all that. And when you get back to the office after an interview, see coworkers’ faces saying “WTF do you think you are coming in at this time of day? eh!” ¬¬

    The great advantage of leaving a job without having another one lined up is that you can take a few days to recharge. And then you can dedicate 100% of your time to finding this new job and prepare yourself better for interviews, polish your portfolio. Be YOURSELF without judgement from coworkers and managers.

    If you feel you need to leave, grab the bull by its horns and GTFO. When the values of the company you work in and yours are not aligned anymore, that’s your cue to move on.

    Thanks Jeffrey for validating my reasons to leave a job. Again.

  9. Good advice – although I’d recommend having at least 6+ months living expenses (certainly if you are supporting others or live in a place where the jobs are few). I’d add that your leverage as an employee is highest at two points in the job/career cycle – when you are about to start a new gig and when you announce you’re leaving. If you’re valued – good managers will want to ameliorate issues you point out. So being transparent about why you are leaving (w/tact obviously) is important if you’d stay assuming those same issues went away. Often times good things are not appreciated until they go away. If for whatever reason you are not valued then it’s time to move on to a new opportunity.

    That said – ask yourself just how unique are my skill sets? How in demand? Sure you can do ‘x’ really well but if everyone else can too then it may not be a differentiator. Also where do you live? Looking for a job in larger metro area (e.g. the SF Bay Area) might provide a greater volume of interviews than smaller metro areas. How big and of what quality is your network? At least 1/2 the jobs I’ve held have been through ex-colleagues or friends.

    In the end just be sure about what you want and realistic about what you have to offer.

  10. Thank you so much for posting this. There seems to be no one out there talking about this really crucial period in most people’s careers.

    I do have a question about a particular situation: I have been submitted for a promotion to a senior position but I think it’s time to move on. It seems to have put a time limit on my search for other opportunities because I don’t want take a promotion and then leave.
    —I love my boss and team but the company is going in a direction different from what I want to be doing.—

    I want to leave without burning bridges, like you say, but feel like leaving right after being promoted would light the flame. What do I do?!

  11. Hey,

    Thank you for this article. I have been thinking about how to apply my skills in a position that would merge my two major interests. This article pinpointed a great way to do that: Freelance…

    Thank you! I will share this article on my twitter: @andaleem
    so it can help others.

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