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Ask Dr. Web—Live

Design your career like you’d design a website. Listen in on this recording of our fearless leader Jeffrey Zeldman and his co-host Sarah Parmenter answering audience questions about their web careers.


Make yourself irreplaceable. Stop waiting for someone to hand you the perfect job. Cultivate the professionally and emotionally healthy worker within, and design your career the same way you design a website. Listen in on this recording of our fearless leader Jeffrey Zeldman and his co-host Sarah Parmenter answering audience questions about how to make your web career longer, better, and more satisfying.

What we talked about

  • Presenting yourself professionally
  • Raising your profile and your rates
  • Mastering the side project
  • Knowing and speaking your mind


Sarah Parmenter: So, hi everyone, and welcome to the sixth A List Apart: On Air event! Our goal for these events is to provide a space for some deep expert discussions alongside some more casual Q&A from the audience, kind of like a meetup but without all the hassle of geography.

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So, I’m Sarah, and I’m going to be moderating today’s event, lucky me. I’m a designer, I’ve been in the web industry for a good while. I’m sure you don’t want to hear about me, but you want to hear about the main man himself, which is—as if Jeffrey needs any introduction—we will introduce him with vigor regardless! So Jeffrey is among one of the most well-known echelons of the web design community. He was the guiding force behind the Web Standards movement and cofounded The Web Standards Project; publisher and creator of A List Apart, founder and co-owner of the hugely popular web conference, An Event Apart. And the books you all probably have on your shelves are also Jeffrey’s company, which is A Book Apart; the iconic blue book which is probably on all your shelves too, that’s Jeffrey’s, entitled Designing with Web Standards; and he also founded the design agency Happy Cog. I’m also exceptionally lucky to call him a friend, and if he was in England, he would probably be called Sir Jeffrey Zeldman, but for now I’m just going to call him my pet name, which is Ziggy. [laughs]


Jeffrey Zeldman: Thanks, Sarah. That was… Uh, wow, that was quite an introduction. I like that, “Sir Ziggy”; I like that a lot.

Sarah: You have been introducing me all year with very nice introductions.

Jeffrey: Yeah, well, you’re awesome. And I think of myself as “Sarah’s friend,” but I appreciate that. I am very excited to be here. I guess “Ask Dr. Web,” since it started as an HTML advice column in the ’90s—in the ’90s, when you were like a baby, Sarah…

Sarah: I wasn’t a baby. I’m older than I look.

Jeffrey: Pretty much. Pretty much. But now it’s a career advice column on A List Apart. Oh, I see—we’re both at home today, we’re both working from home today, and I think I see, is that a lion back there, or a cat? What is that that just went through the door? You do have an animal, right?

Sarah: Yes, that’s my dog; that’s Alfie.

Jeffrey: That’s your dog? Okay. I could only see a haunch…

Sarah: But we can—it’s a lion, if you want.

Jeffrey: …like a blond haunch, so I wasn’t clear what kind of animal I was seeing. What kind of dog is he?

Sarah: He’s a West Highland White Terrier. Yeah, super cute.

Jeffrey: Okay, so like white-y blond. Yeah, yeah, yeah, okay.

Sarah: Just white, but he’s probably dirty, because he’s been in the garden, so.

Jeffrey: Oh, cool.

Sarah: So, today’s topic: so, we’re talking about career advice today, and I know that this is something that you have been speaking about at An Event Apart this year, which it’s been a really wonderful talk, actually. We’ve got some questions coming in from the audience. So, we’ve got a question from Steve, and he says, “How do you keep a team motivated and keen when the work isn’t always exciting?”

Jeffrey: That’s really tough.

Sarah: That is tough. [laughs]

Jeffrey: If the work is never exciting, if it’s your company, you need to take on some jobs that will be exciting, even if they’re low cost or free, right? So if it’s your company, and you’re getting lots of good bread and butter work, but the team is getting demoralized because it’s—you know, it’s all solid, but it’s nothing exciting, nothing to write home about, one thing you can do is try to find an organization in your community that needs your help and can’t really afford you; it could be somebody that helps, a charity, some kind of organization that helps, you can work for them. Another thing you might ask yourself if it’s your company is why is the work uninspiring and lackluster? Doesn’t any project, in theory, have the ability to be made interesting if you’re solving all the right problems?


So, let’s say, I don’t know, I’m doing an ecommerce site for people that make two kinds of white bread. Right? I mean, I’m just trying to think of the most boring—like, you can get it sliced thick or sliced thin, it’s white bread, it’s got all these preservatives in it. So, depending on your relationship with them, maybe you ask, “Can we help you—can we talk to some of your customers and see what else they might want?” You might find out that there are other products, that maybe their customers want organic bread, or gluten-free bread, or something else that they didn’t know about and maybe you can work with them strategically, and that can be the interesting part. Maybe there are usability or accessibility challenges in their interface that you can get everybody psyched about, like we’re going to have—so, this is the most boring site in the world, the client sells two kinds of white bread, or our in-house team, we’re part of this company, it’s boring, but we’re going to make a site that works for someone who can’t see; we’re going to make a site for someone who has no motor skills; we’re going to make a site that doesn’t trigger vestibular disorders. You can find ways in graphic design, or in the usability, or in the research; there’s probably some way to spin it so it’s interesting.

Now, that’s if it’s your company or your freelance project. Most people work for someone else and most people don’t have the discretion over that. So maybe your boss has been landing a bunch of boring jobs, and the boss is not particularly insightful, or particularly… The boss is not the kind of person who is going to just, like, stir the water too much or risk upsetting the client by saying, “Let’s do something interesting.” When I was in advertising, we had a really boring client and we’d done boring work for them for years, and one day the new creative director said to us all, “Do something great.” And we all tried our best to do something great, and he picked the best spots and showed them to the client and said, “Now, I want you to tell me why you don’t have the courage to do one of these commercials.” And they said, “Thank you. We’ll get back to you,” and within 24 hours they’d fired us, and a bunch of people lost their jobs. So, sometimes the boss seems, you know—sometimes the boss goes out there on a limb and it doesn’t work, sometimes the boss… It might be the way he handled it—not what he asked them, but how he asked them; that maybe his thinking that if he challenged them in this macho way, that they’d, like, rise to the challenge, maybe that was incorrect.

But whatever the case, whatever the case, if the boss is not making it interesting or the client is not making it interesting, that’s when you try to find activities within your own team to make it interesting. So, the team, you go to the team and say, “Look, these guys are just selling the stuff and they don’t care if it’s accessible or not, but let’s try to make this the most accessible site that’s ever sold bread, and then we’ll enter a competition.” Or, “Let’s try to write the most funny user messages that are compatible with this client’s brand so that the error messages not only steer the user back on the trail of getting the bread they want, but actually, you know, provide some appropriate comic relief from the frustration they just experienced.” There’s always some way to make even the most boring job—if it’s not coming from the top, it can come from where you are and you can rise up and say to your boss, “We’ve come up with this thing.” You may have to work hard to get your boss to support you, because not every boss is a good boss. Some bosses will go, “I don’t deserve you folks, you’re so creative,” and some bosses go, “It’s just a bread site. I’m not paying you to think,” or whatever. And if that’s the case, you have to look for another job. Or what I used to do is just freelance like crazy. Obviously you can’t freelance on the boss’ dime. So if you have a steady job, you can’t go into your office while you’re on salary and sit there and do your freelance work. That wouldn’t be ethical.

But after hours, your time is your own, and if you find interesting jobs on your own, or with a partner, maybe you’ve got an equally—let’s say you’re a designer and your partner at the company is a developer and you’re both so frustrated at all these boring sites that you’re doing where you have to keep… So, you go out together and you pitch something. I’ve done this so many times when I’ve worked for other people. Like, find a partner and go out and pitch something. The local karate school, the karate school your kid goes to, something where they have a terrible website or… And they can’t afford any better, they don’t know any better, and you go, “Look, we’re going to fix this for you guys, and we have to get paid something for our work, because, you know, we’re professionals. But for $5,000 or whatever, we can do this thing for you,” and then you go out and do those. You do a few of those, and a) you’re supplementing your income, right, with additional income; b) you’re building up a repertoire of potential clients; c) you’re showing that you can do more interesting work, and what’s going to happen is either the boss will see it and start bringing you up to do more interesting work, saying, “Please help me pitch more interesting stuff,” or someone smarter will hire you, right?


So, that’s what I would say. There’s always your own projects. I know that sounds like a cop-out, but… If you have no control over the situation, and you’ve done your best, and it’s not working where you are, then you just make your own projects. And if that fails, make your own stuff; just make your own site about anything; just make your own cool web project and share it, and that can keep you interested.

Sarah: I used to challenge myself with stuff like that. If the project wasn’t particularly interesting, I’d use it as a way to enhance my skillset. So, I’d always challenge myself. “I don’t know how to do this JavaScript rollover,” whatever it is, or when those collapsing segments of things were really in, in the early 2000s. I would sort of challenge myself and say, “I don’t know how to do this,” and if I can do that, then that kind of makes it interesting and I’ve learned something for the next project; I’ve learned how to do some PHP, or I’ve learned how to… It might not be production worthy, someone else might redo it, but I personally have learned how to further some skill. Like, I used to find—like, I would be interested by that, but then I like challenge, so.

Jeffrey: No, I think that’s great. If you don’t like challenge, you shouldn’t be in this business. And I think you’re exactly right: there’s always something.

Sarah: There’s always something that you can do to make it interesting, even if it’s the most boring—I mean, we’ve all worked on boring projects, we’ve all done our time. [laughs]

Jeffrey: Now, you’re talking about self-directed stuff that you can do to make it interesting for you, but you can also do that with a team member. You can make a mini team and say, “Well partner, let’s both try to optimize the…”—I don’t know if we can swear on these—“Let’s both try to optimize the bajeepers…”

Sarah: “Heck.”

Jeffrey: “…the heck out of our CSS,” right? Or, “Let’s teach each other Sass this time, on this project,” right?

Sarah: Yeah, absolutely. That’s the way I got through really boring stuff. Always a way. Always a way. And we’ve always got to be learning in this industry anyway, so you might as well do it on a boring project, because you’re only going to have to come up against it in a project that really excites you when you’ve not got the time to learn. So, that’s the way I always used to approach it.

Jeffrey: Brian Eno, the musician and producer, he and a colleague of his came up with these cards, Oblique Strategies, where if they got stuck in the studio, the card might say, “Honor thy error as a hidden intention.” So instead of erasing a mistake that someone made, a player made, they would go, “Let’s repeat that note.” Like, you listen to some of Eno’s early rock songs before he went ambient and there’d be like a wrong note, and then it just gets repeated until it’s your favorite part of the song. It’s like definitely a wrong note that keeps happening every four bars on this out of tune piano, and it’s like, “That’s a cool thing.”

As a discipline, as a creative person, you can always apply one more filter to whatever you’re working on. So, like, “Alright, I’m going to do this with only three colors,” right? Or, “Let’s figure out a way to indicate links without using color at all.” Give yourself some strange—”Let’s only use sans serifs and still have a good type hierarchy. Let’s only use serifs.” It’ll make the thing have more life and flavor because you brought something creative to the table, and it’ll make it fun because it’ll be a challenge. I mean, the thing that makes work boring is when you’ve done 500 white-bread sites and this is another one. So this time, like, “Okay, we’re going to use a different shopping cart this time,” you know what I mean?

Sarah: Totally.

Jeffrey: You know, our mutual friend, Luke Wroblewski, one of his favorite things to do is figure out how many fields he can remove from a form and have it still be a form, right?

Sarah: I love him for that. [laughs]

Jeffrey: So, like, this is a boring site, but instead of 25 fields for the customer to fill in, and they mostly stop at 12 and abandon the shopping cart, let’s see if we can get it down to one. They’ve got a phone. Like, Luke is a genius at going, “Well, let’s make it obvious that this is a phone number.” Anyway, great question. Really, there’s no limit to how you can make stuff interesting if you work at it. Thank you for that wonderful question.


Sarah: Let’s move on to another question; we’ve got some great ones coming in. So, this is something that you and I have actually spoken about and it’s probably going to get quite heated: “Is there still a market for hand-coded websites or do I need to learn something like Drupal or another CMS in order to stay current with clients’ needs?” That’s from Ragbert.

Jeffrey: Do you want to go first?

Sarah: I… This is something that irks me at the moment, because I got told about two months ago that I—the comment was, “I don’t know who told you you can code,” and that was because it was a website that required no CMS, no anything else apart from a static—static as in the form of just a home page and some information on it, but made responsive for every device out there. And I handed it over in vanilla HTML and CSS, it worked beautifully, it had some Flexbox elements, it was all great, and because it wasn’t built on a framework or anything else, the developer actually turned around and said, “I don’t know who told you you could code, but this isn’t the way that we do it anymore.” And I was like, “It works!” Disgusting.

Jeffrey: Well, that person was a jackass.

Sarah: Yes, he was.

Jeffrey: If you’re doing a one-off site, right, like you’re just doing kind of a brochure site, a one-page site that doesn’t require a CMS, there’s no need to make it more complicated. There will always be a desire, a need… Also, I think you have to be able to write static HTML; even if you plan to use a CMS, you have to be able to write it to begin with. You have to be able to make the thing and go, “Okay, now we’re going to PHP-ify,” or whatever it is. “Now we’re going to make variables so that the customer can come in and change the content and whatnot.” But you always start with static HTML. And I think most sites that do anything are going to need to be on an engine; they just will, because the customer is going to change the content, or they’re selling something, or they’re showing something; or they’re letting someone explore, like in a museum website, where if you look at this then this gets recommended. I mean, there’s always room for that stuff, but… Are they even—I’m not even sure, at this point—could you repeat the question? Are they saying must all websites be on CMSes, or are they saying is there room in this field for someone who codes HTML?

Sarah: Saying, “Is there still a market behind hand-coded websites?” To me, all websites are hand-coded, but. [laughs] “But do you need to learn Drupal or another CMS to stay current?” You do need something like that in your toolbox for sure, but you have to layer it on top of solid skills in HTML and CSS, and then keep layering…

Jeffrey: Or you need a partner.

Sarah: Yeah, or someone who does that for you.

Jeffrey: So, if you’re good at HTML and CSS and your friend is great at ExpressionEngine or Drupal, well then that’s great; you have a good team there, a craft, whatever. Usually with a CMS, there’s so much to the way of thinking that’s inherent in that CMS that you almost want one person to specialize in that because you can go deep, and, “I know what the creator of ExpressionEngine was thinking, and I know how to do this in ExpressionEngine.” But a designer who can’t write HTML, I wouldn’t… There are people who can do all kinds of coding, but they have to start with, say, Bootstrap.

Sarah: Yeah, absolutely.

Jeffrey: And if you gave them a piece of paper and said, “Just sketch some HTML for a website,” they couldn’t do it, they couldn’t write a doctype or in HTML. I think that’s a limitation.

Sarah: Absolutely.

Jeffrey: I do, as an old timer, have a slight prejudice against all the frameworks; I do worry that a lot of sites are bloated because of frameworks. I feel like the frameworks are great for quick prototypes, and then, in theory, whenever possible, someone should come recode from scratch. I know we just worked on an application where the backend of it was done on Bootstrap, and when we were designing on the front-end, it was a nightmare. We had done the thing where we wrote HTML that we thought would make sense with the front-end, and we basically had to start over, start from scratch, because our HTML didn’t map to all the divs that—all the stuff that Bootstrap was expecting. But I understand that I have a prejudice about that stuff, it’s not, you know… I’m old-fashioned, and I really like the power of writing HTML at the top of a page, and close HTML at the bottom. I love that.


Sarah: Yeah, I do too. But—

Jeffrey: We’re always going to need someone to do that, because…frameworks don’t exist without that. Somebody did that, right?

Sarah: Absolutely. I think the other thing, the flip side of the coin is if we were to get a CV for someone who just said, “I am just really solid with HTML and CSS,” we might not think that was enough knowledge to employ—it’s not enough of a skillset; it’s a basic skillset that’s buildable, but it’s something that you will need another “ta-da” on your CV of some sort, because HTML and CSS, although, you know, very, very fundamental, are basic coding languages. So, to me, I think you have to have something else, even if it’s just one thing. “I’m a super great”—I hate the word “ninja”—“at JavaScript,” or something. But HTML and CSS, for me, is expected.

Jeffrey: I love type. It doesn’t have to be, “I’m conversant with frameworks,” it could be like—

Sarah: Oh, no, it doesn’t have to be a…

Jeffrey: It could be, like—I love type. When I buy a new book, I spend hours just staring at the page without reading it, figuring out why the type pleases me or doesn’t. I’ll spend 42 hours messing with type, designing in the browser, trying typefaces. Don’t worry, I won’t bill you for all that time, but that’s just me.

Sarah: Yeah, totally.

Jeffrey: Something. Something. I’m more inclined to hire someone whose résumé says, “I believe in accessible, standards-compliant HTML and CSS” than someone who says, “I’m conversant with…” and then lists a whole bunch of frameworks and tools. That’s me. That’s me; that’s my prejudice. But I always feel like if someone has these basics and is committed to semantic, accessible HTML, that’s the person for me, and they can learn those other tools if they have to. But if someone’s a master of the tools but they don’t actually necessarily know about progressive enhancement or accessibility, I worry that they’re going to make big, bloated sites that I wouldn’t really be proud of the underpinnings of those sites.

Sarah: Yep, absolutely. Totally agree with you on that one.

Jeffrey: High-five!

Sarah: Yeah, woo! Geeks! Geeks unite! Okay, so this is from Adam: “I’ve been unemployed for six months and I live in an area devoid of web design or development jobs. I’m not able to relocate. Remote has become my only option but is insanely difficult. I have several sites I check, but do you have any tips?” So, relocation jobs.

Jeffrey: Well, We Work Remotely is a great service for that. They’re actually an advertiser on A List Apart, but I’m not just mentioning them for that reason, I’m mentioning them because it’s a great service. It’s weird, I’m curious—I wish I knew what part of the country Adam was from. I mean, I just read a wonderful piece about coal miners in West Virginia who’d been basically put out of work for like ten years, who are learning to be coders.

Sarah: Oh, I heard about this! It’s wonderful, yeah.

Jeffrey: Yeah, it’s wonderful. It doesn’t mean—it’s not like, well, so everyone who loses their job will become a coder, or every labor job is gonna—no, nothing simplistic like that is going to solve all our problems. But I wonder if the reason it’s difficult is because maybe the contacts aren’t there. There’s something to be said for being in a… Like, if you live in a city that has a decent airport and you could go fly out to meet a client in a bigger city once in a while if you had to, to pitch the job and then to present, that would help. I know that even with remote work, if you’re all web people, if you’re being hired by other web people, they’re usually pretty good about saying, “I don’t care where you live. I’ve seen your code, it’s great,” or, “I love your design, I’ll hire you.” If you’re looking for jobs from other web people who maybe already have their own clients and need help, that’s where you’re likeliest to work well as a remote person, no matter where you live.

If you’re looking for your own clients, it’s going to be tougher, because to some extent, San Francisco, Austin, New York, London, Chicago—the bigger metropolitan places—they don’t have all the clients, but it’s a little easier, right? It’s a little easier as a freelancer, if you’re in Chicago, to go talk to the president of a bank in Chicago at pretty much short notice, and it might help you get that job. Or Philadelphia, or Seattle, right? It can be harder in a smaller town. Then again, if you’re in a smaller town with a decent economy, maybe you can go to local businesses and say, “This is what I do, and I notice you have this website, and can we talk about it?” I mean, cold calling, cold pitching is hard, but you put on a suit, you bring an associate, and maybe you try that. If you’re in a place where the economy itself is—and I’m getting the vibe that maybe they’re in a place where there just aren’t a lot of successful, thriving businesses, they can’t move because of family reasons or whatever, so they’re sort of stuck there… I think the best thing you can do in that is apprentice yourself to companies that are looking for a great designer/developer and don’t care where you’re located, and have their own workflow. And find a good one where you’ll be challenged and interested and appreciated and paid well. But I think that’s going to be your safest bet.


Sarah: When I was—because I’m in a really small town called Leigh-on-Sea, which is quite a—it’s a fair way, in English terms, outside of London; the tech scene is next to zero here, really. But I figured out quickly that that was obviously going to be a problem with gaining clients. What I used to do was go up to London, schedule a week in London where I would do back-to-back meetings, because otherwise your productivity just goes to zero when you have to travel for a couple of days. But what I would do is sell tickets to local events where I could share my knowledge with a vast majority of people. So, for £50 a ticket or something, “Come along and I’ll teach you about the best way to do a…” Nowadays it would be social networking or something like that. And the businesses don’t consider that as much of a considered purchase as actually using your services, which may be out of reach for them. So you get a room full of 50 people paying £50, that’s good bread and butter money to tide you over while you are using those freelance services that you can find online. That’s what I used to find, that’s what I used to do.

Jeffrey: And it’s a great way to get leads.

Sarah: Yeah, and then you position yourself as an expert within your field locally. And they might not be the big ticket clients who come back until you’re able to keep a roof over your head, but enough of those people will create a residual income, which means that you can at least feel comfortable that your mortgage is being paid before you’ve even gone on to some of these sites for remote jobs. Authentic Jobs is also very good for remote jobs, because you can actually click—

Jeffrey: Absolutely. Authentic Jobs is fantastic.

Sarah: Yeah, you can click something at the top. So yeah, anyway, let’s move on to another question—

Jeffrey: Oh, I just wanted to say: go for something like that, do the best that you can when you land that thing, and they’ll keep hiring you, and that’s what will help.

Sarah: Oh, yeah. The issue is that—I’ve found that a developer who produces—or a designer, it doesn’t matter—who produces something on time; if they say it’ll be on your desk tomorrow at 5, the people who actually get that thing on my desk tomorrow at 5 are the people who stick in my brain. The ones I don’t have to follow up with, the ones who I don’t need to push to work, who just do it, I pay them straight away and then they do the job again, and I pay, you know. Those are the best ones that stick in my brain.

Jeffrey: And there’s never enough.

Sarah: There’s never enough. Like, that whole clichéd saying that I’m sure comes from Pinterest, “Go the extra mile because it’s not crowded,” is so true in the web industry. [laughs] So true. So, a question from Sarah, wonderful name, wonderful name: “I’m a one-woman web designer and developer who is learning how to make a living as a freelancer and still looking to get systems in place. I’m wondering, do I need to use Git since it’s just me, or am I missing out?”

Jeffrey: Well, you’re a one-woman business. Do you use Git since it’s just you?

Sarah: I didn’t until—I had an account for years, and I didn’t because Git’s always been one of those funny things that, for me, kind of confuses me, still. I use it for if I’m working within a team on something, and I always have. But personally, I just use Dropbox for everything.

Jeffrey: And folders.

Sarah: Folders. You know, keep everything well organized. I still have so many folders on my hard drive that’s like, “Desktop 2006,” where I just get angry and put everything in there. But I wouldn’t say do that. But no, I don’t use anything, really. And even I’ve gone back to old-fashioned lists with a pen and paper, to be honest. Like Dropbox, sometimes I’ll use reminders, is enough for me, really. I don’t think, as a one-woman—I think the most important thing, if you’re going freelance, is just to make sure your accounts and stuff like that is in place rather than worry too much about having Git, because that’s the stuff that really creeps up on you and suddenly you find yourself in accounting hell for one month of the year. I find that that’s the stuff to focus on, rather than systems that only you are using. Once you have to work within a team, Git is fantastic, but…


Jeffrey: Or an affordable bookkeeper.

Sarah: Yes! An affordable bookkeeper.

Jeffrey: One of the things that changed my life was finding a—now I have two, and they’re really good, and an accountant, and it makes all the difference in the world. I used to write in the margins in my checkbooks. I once paid—I won’t say who—I once paid this designer $20,000 twice when I was only supposed to pay them once because I am so…I have whatever emotional problems with numbers, and I was writing everything in the margins of a checkbook. And once I turned it over to a professional, it was sort of like, “I don’t do my own dental work. Why would I…” You know? But I think Git is something that you know when you need it, just like you know when you need exercise or you know when you need therapy. You’re on a project, it’s complicated, people are overriding each other—you need Git. You’re doing something by yourself and you dump everything in basically a digital junk drawer and you call it something like, “Final Final Final (no, really) Final This Time.PSD” or whatever, you don’t need Git, you just… Yeah. It’s one of those growth things that happens when you get to that point, which I’m sure you will.

Sarah: Totally. Good luck with that, as well, because yay for people coming into the industry. So, a question from Marsha—hey Marsha, recognize her: “Coming from an agency, then to graphic design and freelance, and then self-taught web development on small sites, I feel I need to concentrate in one area that is short on talented people, i.e., CSS animation. Thoughts?” Good question.

Jeffrey: Wait, what was the question? I heard, “CSS animation” and then I didn’t hear anything else.

Sarah: So, she’s coming from a traditional agency, then graphic design and freelance, then to self-taught web developer. So, does she need to concentrate on something that is essentially going to bring more value to her as a person and her as a team member? So, something like CSS animation or anything else that we think would be valuable where there’s less people doing it; less talented people doing it.

Jeffrey: That’s tricky. I could answer that both ways. To me, it depends on her. If you’re just a great designer, then just be a great designer. There’s never enough. On the other hand, if you have a real talent for animation or a real talent for research, and you’re more passionate about that than anything else, then specialize. It’s really… Look at the things that you’ve been happiest—look at the things you’ve done. How have you paid your bills in the last two years? Look at the things that you’ve worked on that have made you the happiest, and try to figure out what they had in common. Do what you would do if you were your own client. Do the research. Look back at what you did and say, “What do I know about this person? Well, they did that, and this got a lot of attention, and was there anything to it? Those little animations were a great touch. Maybe I should keep working with those.” Or maybe those little animations are just part of your repertoire and the big thing is that you’re just a terrific designer. There’s never—there’s so many people in our field and there’s so few really strong designers. And then of those, there’s just a few that are great. So, you know.

Sarah: Agreed. I think it’s one of those really difficult things—design is one of those really difficult things, where it’s a bit like bodybuilders. You don’t suddenly get muscles out here. You have to train your design eye, and a trained design eye takes many years to obtain, I think. There’s very few people who naturally have that. You have to train it over many, many years, and I think that’s where—there’s less people nerding out on design nowadays, personally that’s what I think, and that’s why we have a lack of them. So I love people who nerd out on design stuff. There’s not enough.

Jeffrey: You think there’s less? You think there are more… What are they focused on instead?

Sarah: I think they’re focusing on the codebases, and that’s right, because engineering-side, everything’s gotten way more complex, and it was going to, with the inventions of all these devices, it was only going to get more complex. But with that, I remember a time when you’d go on the internet, someone would launch a site and we would all bombard that site and be like, “That’s beautiful! Oh, it’s just beautiful!” and you would totally nerd out on it for a day. I remember when Colly, Simon Collison, launched his site with all of the, like, old-fashioned—you know what I mean, butterflies and—

Jeffrey: You moved around on it, yeah.

Sarah: Yeah, it was like butterflies and caterpillars.

Jeffrey: Yeah, it was fantastic.


Sarah: I remember when that came out, it was a truly great piece of art. Nowadays, we can’t do that as much because of the limitations of what we’re trying to do. I can’t remember the last time I went onto a website and thought, “That doesn’t look like every other website on the web right now! That’s just a beautiful piece of art.”

Jeffrey: Not since K10k, really. That’s the time you’re talking about. You remember them, Kaliber10000? It was so cute. It was like an adorable—it was like a demented pixelated Disney World was created. It was amazing.

[Alfie starts barking]

Jeffrey: Hi, dog!

Sarah: Oh, someone—I think it’s Amazon trying to deliver. So, we’ll just ignore Amazon. Yeah, it’s a really difficult one. I always like people who nerd out on strange things, like data. I like those people too, who come into meetings and are like, “Ah, hang on a minute! Have you thought about the fact…” I like those people as well.

Jeffrey: So, one of the people that shares an office with me is Nick Sherman, and he’s one of maybe 100 type geniuses who are working now. Maybe it’s not as many as 100, I’m just—I don’t want to be arrogant. There’s a lot of people probably in other languages that I don’t know of. But he’s one of the few I know about. And just having him around, and just being able to go into his office and say, “What do you think?” He has so many ideas because he thinks about type! So if you really have a passion for a specialty, again, like the Github question, you’ll know it, and you should just go for it. But if you don’t, then trying to graft it to your—like going, “I think I’d be more marketable if I…” I’m not sure. I’m not sure about that, and maybe just believe in yourself and keep going.

Sarah: We have a similar question along the same lines from Azy: “My career thus far has been primarily copywriting and content strategy in team settings. To what extent is it worthwhile for me to develop web design and coding skills?” Similar vein of thought.

Jeffrey: What do they want to do now? Do they want to be a web designer now?

Sarah: Copywriter and content strategist, and is wondering whether it’s worthwhile developing web design skills.

Jeffrey: So, if they intend to continue as a content strategist, it probably would be helpful to them to get a little background in HTML and other web design skills, just to have more knowledge. Just like if you’re never going to really be an engineer, but you know a little bit about JavaScript, you at least understand the theory of it, it helps, right? And if you’re the kind of designer who’s really not going to be a coder but you understand HTML and CSS, it helps. I would say that. Now, if you want to transition and become a web designer, then they have to learn that stuff. But I didn’t get that sense. I got the sense—the question is a little vague, but if they want to stay as a content strategist, it certainly wouldn’t hurt. It’s a nice idea.

Sarah: Yeah, I think—I’m just going to call it, but I think she wants to stay primarily as a copywriter but is wondering if it’s worthwhile tacking that on to an existing skillset.

Jeffrey: I think it would make you better at your job because you would have more of a sense of, “I’m not just writing for this box, or this box can become a box like this instead,” or, you know, just the more you know about all of the stuff, all the ramifications, the better you can be at doing your job at writing for those boxes, as it were. The more you know about web design, the less you’ll be writing for boxes and the more you’ll be able to think of it as… what does Karen McGrane call them?

Sarah: Systems.

Jeffrey: Chunks.

Sarah: Oh, chunks.

Jeffrey: And right, and Brad Frost calls them systems, and they’re both right.

Sarah: Yeah, or atoms, or whatever Brad’s come up with this month, which he’s just so clever.

Jeffrey: He is clever.

Sarah: He is so clever. One clever, clever chap. Katie has a kind of similar question as well, but with a different thread. So, she’s a freelance UI designer, and she finds that freelance and remote job listings are often looking for a user interface, user experience, plus a developer rolled into one. As a UI designer, great UX is always part of her design thinking process. However, she’s not a developer. Does she need to be?

Jeffrey: These are for positions, or these are for freelance gigs?

Sarah: Says, “Finds that freelance and remote job listings are often looking for all those things rolled into one.” I would be wary of a company that would roll a developer and designer role in…

Jeffrey: Me too. Nick Fink had this thing way back in the early 2000s, he shared it on MetaFilter, so I’m sure if I could remember the keywords, I could look—I could Google it. But it was basically job listings he was finding at that time, and they were like, “Looking for web designer, must know Flash, Illustrator, JavaScript,” they listed every kind of backend code you’d need, and it went on and on and on. And I was like, those aren’t really design jobs anymore, those are just, “I need five people, but I’m only looking to pay one,” is really what they’re saying.


Sarah: Yeah, absolutely.

Jeffrey: It sounds like she should stick with—if she sees user interface and user experience as interconnected (and they are), then she’s already good at her job; very good at her job. And again, a little code—if she had to prototype something, that wouldn’t hurt. But making herself a master of engineering, no, that’s ridiculous. You’d be getting a job at a company you don’t want, or a freelance gig for people you don’t want to work for. If it’s really a freelance gig, you can come back and say, “I’ve got this great engineer I work with, and I do the UI and UX, and between us we’re going to charge this amount of money and you’ll get a great project.” That’s how to handle the freelance side of it. And the career position side, look at it as a filter: you don’t want to work for someone who doesn’t know the difference between an engineer and a designer.

Sarah: Nope. I remember a few—I think it was a few years ago now—I found a job listing where it was parking attendant and web designer rolled into one. It was the most amazing thing I’ve seen in a while.

Jeffrey: You’re making that up. You’re making that up.

Sarah: No, I’m not! I’m going to find it for you. It was amazing. It was amazing. It lasted about half a day before it got pulled down because the traffic kicking up from the web industry was just phenomenal. [laughs]

Jeffrey: Really? “Must know HTML and make sandwiches.”

Sarah: Yep, “and make a good cup of coffee.” So, Jacob says, “It’s relatively easy to get experience designing apps and websites, but where would you go to gain experience in service design or designing for connected experiences?”

Jeffrey: Take a summer job at Disney.

Sarah: They have good user experience. They do.

Jeffrey: I would go to a school. Like, I teach at School of Visual Arts, they have an interaction design program. It’s a graduate program; a two-year graduate degree program. I don’t have enough of that kind of experience myself. In fact, I have none. So, I don’t know what kind of job or what kind of industry you could go into to just get on-the-job training like that. I do think it’s worth, if you have—by the way, in our school, and I’m sure this is true in all schools, people have lots of different diverse professional background experience. They’re not kids, they’re adults who have work experience. So, if you’re a designer and now you’re looking to move into this other field of design, you’d probably do well in a program like that. There’s the Unicorn school, right? The Center Centre that Dr. Leslie Jensen-Inman and Jared Spool have started in Tennessee, in uh… Not Tennessee. Why am I blanking on this? I’m such a jerk; I sound like such a New York person. “It’s Tennessee or Cleveland or somethin’.” I’m sorry. I’m really sorry.

Sarah: I think it is in Ohio, isn’t it?

Jeffrey: No, it’s not in Ohio. [laughs] Oh, man. Okay, now you sound like a British person.

Sarah: Oh, gosh. It’s somewhere!

Jeffrey: Look up “Center Centre.” Look up “SVA MFA IXD.” There’s a bunch of programs like that at various price points, and I know that that works, and I know that SVA turns out really, really brilliant students who all immediately work at stuff they love. I don’t know anyone from the program who’s, like, looking for a job or feeling sad. I don’t know of any on-the-job ways to do that, but some of our readers might, and listeners might, so maybe check the comments if this gets posted as a thread on the A List Apart feed, maybe someone will have insight into that.

Sarah: A question from Jeanne: “Considering the push to expand H-1B visas for lower paid foreign techies, which skillset do you think will offer the most opportunities at the highest rate of pay?”

Jeffrey: What visa are you looking for, Sarah?

Sarah: I would very much like the O-1—

Jeffrey: O-1A, right?

Sarah: No, just the O-1. I think I just like the title of it, which is the “alien of extraordinary ability” visa, which is hilarious. But I’m not—I don’t know about the H-1B visas, but I guess it’s irrelevant to…not irrelevant, but as in it’s just what skillset do you think will offer the most opportunities at the highest rate of pay, because they’re going to be looking for that on a visa.


Jeffrey: I’m going to say engineering. You won’t go wrong with engineering. I don’t know which specific things, but I think the more—you should certainly know all the front-end codes, know platforms, popular middleware, backend. I think that’s where people tend to spend money on bringing people in from other countries. I think they’re less likely to bring content people in, or designers in from other countries—not unlikely, but just less likely, usually because, well, content is more local anyway, right? If I’m bringing someone in from Czechoslovakia, do I want to bring a writer from Czechoslovakia to write idiomatic site copy, or do I want to bring a developer from Czechoslovakia? I’ll probably bring the developer.

Sarah: Yeah, totally.

Jeffrey: And that’s where most of the jobs are anyway, whether you’re traveling or not, whether you’re migrating or not… The jobs are in coding right now.

Sarah: Yeah, absolutely, more than we’ve ever known. It’s great for our industry. So, I have a question for you: what do you look for when you’re hiring people at Happy Cog?

Jeffrey: Is this from you, Sarah?

Sarah: Yeah.

Jeffrey: I personally have never hired anyone that didn’t write, didn’t have a blog. Didn’t have to be a great blog, but they had to be able to articulate their thoughts. And we have Cognition, we have a site blog, it isn’t there to get customers and that speaks to the industry. And it’s just there so that the really smart people who work at Happy Cog can share their thoughts. I think if you can articulate your thoughts in writing, even though that’s really hard, you’re going to be better in meetings, you’re going to have a point of view; you’re not going to roll over and say, “The client said I should make the button blue and make it bigger, so that’s what I will do,” but instead will go, “What is behind the client’s request? What are we really trying to achieve?” So, I look for that: the ability to present; the ability to articulate and think, which leads to the ability to present.

If public speaking makes you nervous as hell, writing is a good way to, you know, work your way into that. I wrote before I spoke. The first time I was asked to speak, Lynda, of, asked Jeff Veen and me, and George Olsen to speak about web standards in 1998 at, like—at a computer—I don’t remember what it was. I was terrified. I just remember I stood behind the podium and, like, went… My little brother used to be scared and wouldn’t talk. My mother would say, “What did you do today, Peter?” and he would go, “You tell,” and I’d have to tell what he did. And that’s how I felt, like with Jeff Veen, like, “You go. You tell them.” I was terrified to speak. But I kept writing about it, and now you can’t shut me up. So, I would say a person who’s articulate, who can present, is someone that I can trust to take the material to the client, represent the studio’s point of view, understand and respect the client’s point of view and all that other stuff. I’ve seen over the years the person who’s articulate is the person that everyone talks to. So, if you’re the quiet brooding type, you may be the best designer in the room, but you’re going to have less power to change things and less power to achieve good than the person who can articulate.

Sarah: Absolutely. So, a question from Zack: “Starting as an art director, my job at a start-up has pushed me to learn front-end and backend development, marketing and digital strategy, and business development. How can I position myself for a new senior role in a different company?”

Jeffrey: I’d love to know what his title is now.

Sarah: He started as an art director.

Jeffrey: But now he’s a director of marketing? Is he a director of internet?

Sarah: He’s at a start-up and he’s being pushed to learn front- and backend dev, marketing, and digital strategy, and business development. That’s quite a list of job titles.

Jeffrey: Is he a design lead, or a development lead? It sounds like he—I mean, he could be in charge of the web division, if they had one. He should look for a senior position that involves an understanding of and the ability to supervise designers, developers, and marketers. It might be a design and development job, but he interfaces with the marketing people and his experience makes him good at that because he speaks their language too and he doesn’t have that knee-jerk prejudice some designers and developers have of, like, “Oh, the marketing people are in the room,” right? But he can actually be respectful and good with them.

I don’t think he should probably—I don’t think he would look for a marketing position, because I think he wants to be in web. So, look for a senior—look for or try to create; come in for a job that isn’t quite right and then talk to them about why—ask them so many questions about how they’re organized and how their workflow works and then say, “I’d like to think about it” and then come back and say, “Really thought about the organization, and I think if we maybe took these two silos and un-siloed them and put them together, I think I could…” You know what I mean? “You’ve got your developers on this floor, your designers on that floor, and the marketing people in a building down the street. I think we should all work together and I’m the kind of person that can actually help, you know, either be in charge of that or work on that in tandem with someone above me.” I don’t know, I think there’s lots of ways to leverage—I hate to use that word, sorry—but to leverage all that stuff that he’s got.


Sarah: So, another question from Adam: “JavaScript seems to be the most wanted item from employers. Sadly, web standards and progressive enhancement seem to be entirely optional. Many pros like you promote those, but JavaScript seems to be king. Why is it not catching on more? To me, JavaScript feels like the next Flash.”

Jeffrey: It doesn’t have to be.

Sarah: No.

Jeffrey: JavaScript is at the point where we can make apps on the web that are just as dazzling as the apps on our phones, and that’s very exciting to business owners, just like in a previous generation Flash was really exciting because it let them do the kind of marketing they were doing on TV at a fraction of the cost, right? And so now they’re like, “Wow, we have this one platform where we can develop multiplatform apps basically with JavaScript, we can make apps that work everywhere.” So, nothing is wrong with any of that. I think the person who understands progressive enhancement knows how to do it in such a way that the content will be available for everyone, even if they don’t have that full app experience.

I do hear a lot from people that progressive enhancement is an optional extra and that everybody has JavaScript, and I just disagree and I get angry. It’s not about people not having JavaScript support or having devices to support JavaScript. It’s about what happens when the script fails to load? And, you know, so many people have talked about this, right? We’ve both heard so many smart people talk about this. You know, all of a sudden someone goes to your site and because one script failed to load, there’s nothing there. I think just as a fail-safe, if you want to make sure that everyone is going to have an experience and interact with your content, it makes sense to start with HTML and forms and all that stuff, make it so that people can access something, no matter how they choose to come to you, and build up from there. But it’s a struggle. I think you have to use data with some people, and show, like, the numbers. Luke Wroblewski has published, if you go to, lots of numbers where if this tiny percentage of scripts fail to load and you’re Google, that means that 400 million people couldn’t download your app for a day, and that’s bad business, right?

So, I think we have to do the same kind of argument we did in the past with web standards, and I’m planning to talk about that next year at An Event Apart; I’m actually planning to talk about designing with web standards in 2016, because I think while we have a much bigger opportunity than we’ve ever had, it’s also much more challenging because there’s this sort of blindness. I think JavaScript is the friend of HTML and CSS, and they really work together very well, but I don’t believe that you can just use JavaScript and not worry about the rest of it. I think that’s a tragic mistake.

Sarah: No, absolutely. So, a question from Matt: “We’re a small web/motion shop of senior folks that were Flash experts then and now the HTML5 equivalent. The agency work we used to do seems to be more of a commodity. How do we position ourselves for the best jobs for our skills custom complex?”

Jeffrey: What do you think?

Sarah: [sighs] It would be helpful if my dog would stop barking, number one. This is really difficult, because I think that the agency model has changed a lot in the last four, five years. I’ve noticed it; I know other people who have small teams of people have noticed it as well. Positioning yourself for the best jobs in that market… I think working with other agencies, if you are very niche like that, I think the easiest thing for you to do is to position yourselves as expert—like with anything that you’re an expert of—is to work with other agencies and tap those very defined skillsets onto an agency that might not have those skillsets. I’ve always thought that’s the easiest way to go with something like that.


Jeffrey: Absolutely.

Sarah: That can be very difficult, as well.

Jeffrey: I have some friends I used to share a studio with, and they were like the secret ingredient for the ad agencies in town. So, the ad agencies in town—and again, I’m in New York, there’s a lot of ad agencies here—so, the ad agency would say, “We’re doing this commercial for this great wine, and we’re doing all this other stuff for this great wine,” and the manufacturer—it’s a rare wine, and they want an app that will let people—almost like a Foursquare for this wine, that will let people know, “How close am I to a…? I love that wine, but not every restaurant carries it, let me find a restaurant that’s serving this wine right now.” And, you know, the agency sold the client on that idea. They had no idea how to build that, they just had the idea of doing it, and then… It’s weird, in the world of apps, everyone can have an idea. Like, everyone invented Facebook, but one team executed it and made the money. In this case, there’s another way to make money, which is just be the secret ingredient for these agencies, and these people were very successful. They’ve since recently changed their business model again, I’m not even sure why, but they burned out, they were too successful and they were doing too much work. But if that’s not a worry to you, they got so much work just every time an agency needed something amazing to turn around quickly to the client.

And for the agencies, it’s the client’s money and expense, it doesn’t mean anything. They throw money—they would throw money at these people. I remember them saying, “We can basically support ourselves and make our own app and hopefully don’t go out of business, or we can make other people’s apps and make a fortune,” and that’s what they did. It sounds like, you know, the HTML5 equivalent of that would be a very fine option for these folks. So, tie up with your city’s ad agencies, do a presentation where you show all the agencies what you’re capable of, and show them some of your best work, and then the reason you’ll stand out from the others is because you’re the one pitching the agencies. There may be others who can do what you do, but they’re off struggling somewhere and you’ve gone to all the ad agencies in town and kind of locked them up. It’s like owning it because you went there first, right? Just like if I came up with something like Facebook today, even if it was five times better than Facebook, it wouldn’t matter because Facebook owns the category; it’s done. That war has been decided. So, you can go out and do that. And anyone listening that’s in a similar position, find the ad agencies in your town and do that.

Sarah: Totally. Absolutely agree with you on that one. So, we are just coming to the end now. I don’t think we have any time for any more questions, so we’re just going to round up everything that we’ve said, and we’re going to have some updates. We’re going to have the video for today’s panel on the site in the next couple days, I believe, and the transcript is going to be on early next week. And other events? Next one next year, is it, I’m guessing?

Jeffrey: We don’t know when they’ll be yet. We’re figuring that out now. We’ve gone into a little huddle at A List Apart, and we’ll come out of it soon.

Sarah: Awesome.

Jeffrey: Many things are happening at A List Apart.

Sarah: I’m guessing it’ll all be on the site for anyone to look at whenever there’s news about the next event. And we must thank Pantheon for being the sponsor, so check them out at

Jeffrey: You say that so nicely.

Sarah: ”Pantheon!”

Jeffrey: That English way that you say that is great. I say “Pan-thee-awn,” it just doesn’t sound the same. “Pan-thee-awn.”


Jeffrey: But the way you say it, “Pan-thee-uhn.” I don’t know.

Sarah:Pan-thee-uhn, website management platform.”

Jeffrey: Very good. I like that.

Sarah: [laughs] There we go. So, yeah, that’s about it for today. Thank you for the chat.

Jeffrey: Yeah, thank you, Sarah. You’re incredible. Thank you, Mica. Thank you to our team behind the scenes, everybody doing all the stuff. And thank you to Google for making Hangouts. What a brilliant thing.

Sarah: It is fabulous. Thank you all, and we’ll see you all on Twitter, I’m guessing. [laughs]


Google Hangout
60-minute audience Q&A


December 2015
1-2 PM EST


Sarah Parmenter

Sarah Parmenter owns You Know Who, a small British design studio now in its tenth year. She specializes in iOS user interface design; regularly contributes to various online and printed media; and speaks at conferences all over the world. Sarah’s straight-talking nature and no-fuss approach to projects have landed her many great contracts over the years, with various well known brands in the UK and abroad. Photo credit: Craig and Kate

Past Events

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Ask Dr. Web—Live

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Pattern Language: Responsive Style Guides

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Sass Talk

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Designing for Performance: Can We Have it All?

Everyone wants sites that are responsive, beautiful, and fast. Do we need to make tradeoffs? And whose job is performance, anyway? In this event from February 26, 2015, we asked a panel of designers and developers from both in-house and agency teams to share their stories, strategies, and case studies. Watch the video or read the transcript here.

About our events

Bringing the feel of a local web meetup to the online space, our community-focused sessions discuss the events of the day—or hour. We bring together experts and readers for realtalk—not just presentations. Join us to hear new voices, ask tough questions, and take our community’s conversations further.