Thanks Kelly!

"How They Got There" was actually inspired in part by "Founders at Work." If you haven't read it, that's a fantastic resource for anyone interested in how tech companies get built, and really how people turn their ideas into reality. I read that several years ago and always wanted to read something similar about designers.

So a while ago, when I was between projects, I decided I would actually take it on and do it myself. I reached out to 14 wonderful designers I know and asked them to each spend about an hour with me over Skype/Hangouts. It sounded like it was going to be a fairly easy project in the beginning, but the editing of all the interviews into readable form was much more work than I anticipated.

I'm really happy with the end result though; a few people who have read the early drafts have said they can't put it down, which is really flattering.

As for how to juggle many projects at once, I don't know any killer secretes. My advice is to be really passionate about each of the projects you take on—there's no other way to get them done than to be able to sustain your enthusiasm through all of the ups and downs.

Also, I guess I've discovered since my wife and I had kids (we have a 5 yr old and twin 2 year olds) that having less time than you would like really forces you to make decisions about how you want to spend your time. I wasted so much time when I had tons of time to devote to side projects; now that I have nearly zero free time, I find myself conversely more productive than before. Weirdly.

@Daniel: I'm really proud of what we did at the Times though I tend to get a bit too much credit for it. (No idea who wrote that line on my Wikipedia page.)

That said, when I joined in 2006, the digital design team lacked cohesion, and was separate from the newspaper's art and design team. I rebuilt the team from scratch and hired about 10 or 15 of them, many of who are still there. For a good deal of my tenure, we worked hard on integrating the team into the operations of the larger news and business org. I also tried to make it more fundamentally a product design team than it had been before. That was kind of foreign to designers at the Times; most of them had worked in the more traditional editorial model, which of course produced wonderful stuff for print. But we tried to think of ourselves as designers of digital products more than editorial designers.

It's been my avatar so long that I don't really even remember when I started using it or where I found the image. But I remember when I started using it I decided, “This is going to be my official avatar and I’m going to use it everywhere.” Partly that's because that old Adam West show has a special place in my heart—it's one of the first shows I remember watching as a kid—I wrote a little about this in this blog post. Also, I really liked that old David Byrne quote: “People will remember you better if you always wear the same outfit.” Over the years I've started to introduce actual pictures of my real face in various contexts where I think the Adam West avatar is a little inappropriate, but I'll hang on to it as long as I can.

@Billy: I talked a little bit about the process in my blog post here and Wired wrote a bit about it in this article. But to recap: Adobe asked me to propose an idea for a tablet app; I worked up some thoughts for an early prototype of LayUp; they assigned an engineer to work with me to rapidly prototype it; we put it in front of a panel users to get their reactions; they then assigned a larger team to it, that I consult with regularly. The whole experience sounds similar to the one you had at Threadless, which is to say it's been a fantastic collaboration. I'm continually impressed with how industrious and effective and clever the team has been in bringing it to life.

As for whether part of LayUp's functionality will be available through Adobe's SDK, I think only Adobe's SDK team can answer that. Speaking only for myself, I imagine that if the answer is yes, it would be a qualified yes—meaning it won't be out very soon. Hope that's helpful.

@Joe: This is a really insightful question; thanks for asking it and thanks for your article on Wildcard. You're really right on the money when it comes to the challenge we've taken on—we are trying to solve a very broad problem, which it's our duty to overcome a number of obstacles with adoption and marketing.

We did spend a lot of time early on experimenting with a very narrow focus. Ultimately though we decided that building a broad product was the best way for us to start putting our ideas into practice.

Normally I would be reluctant to follow this approach, but Wildcard the product is not the entirety of Wildcard the company. We have a number of initiatives that are tackling this problem from multiple angles. Specifically we have a partnership program that helps brands get their content into our browser as cards while at the same time readying that content to be compatible with a number of card platforms, not just ours. We also have a developer SDK that is in the works that will make our functionality more portable—it's a pretty compelling argument for our big picture perspective on cards.

All of which is to say we're just getting started. I've said many times that we don't at this problem through the lens of months but rather years—we are trying to effect a fundamental change in how people interact with mobile content, so the initial efforts you see are all foundational, and will evolve and change over time. Hope that helps.

@AJK: In the same order you asked…

• Transitioning from designer to design manager wasn't that difficult for me in terms of giving up design and being able to "direct" effective design work. But it was really hard for me to learn how to work effectively with people. It took a long, long time—years. In fact I still don't consider myself "done" in this regard.
• First I would say that there are self-taught designers all across the age spectrum. That aside, yes, I do think older candidates do face a challenge versus younger designers, at least insofar as this is true across all industries. One of the most valuable things to any designer is the time and flexibility to learn new skills, ideally without incurring extensive costs relative to their standards of living. Younger designers really have the edge here; they can acquire new skills very quickly with little impact on their standards of living. I wish this weren't true—not least because I'm getting older—but it is.
• No, I don't believe this is true at all. If you look at Behance or Dribbble, you'll see a tremendous amount of self-taught talent, particularly from Eastern Europe and South America. Stateside, it might be a different question—in my experience I've seen relatively little upward mobility in the demographics of designers. At the same time however, I don't think schooling is a prerequisite for design employment; that's been true for the past decade and I don't necessarily see that changing any time soon.

@Yolp: When you say "tools like your Adobe app," can I assume that you mean creativity tools on mobile phones and/or tablets? If so then the answer is yes, I definitely think that the design process will, more and more, start migrating from the desktop to mobile devices, and to the iPad in particular. It's such a powerful, capable tool, and there is so much about our design processes that is inefficient and broken that there's tremendous opportunity for tablet apps to help reinvent the way we tackle design. So yeah expect lots of change in the next five years.

As for your second question, I've been really encouraged by how adventurous digital publishers have been with editorial design in the past few years. There have been some really high profile projects from big name publishers, but what really excites me is how even startup editorial products are embracing the values of editorial design. Pitchfork and The Dissolve come to mind as two publishers producing fantastic content who are frequently applying custom design solutions on a per-content basis, to sometimes stunning effect. I don't really pay as much attention to editorial product design as I used to, but when I see examples like that I sort of wish I were still in the mix doing that kind of work. Sort of!

I really do think that you should develop a portfolio of projects that you're proud of. I don't think that supplants the Dribbble page; any good employer or client will look at both. But given two designers of equal talent, each with equally impressive Dribbble pages, I personally would go with the one who has gone to the trouble of formulating a coherent portfolio that tells the story of who he/she is and what he/she is good at and where he/she wants to go with that talent.

As for whether to stick to freelance or to go for a salaried job: I know this isn't going to be the answer you're looking for, but it all depends on you and your particular circumstance. Both paths have worked for all kinds of people.

Finally, I don't mean to be crass, but this is exactly what my new book How They Got There is all about. If you want to learn how 14 designers who have "made it" actually "made it," sign up for the release!

@Christian: I'd say that it was "more of a revised way of thinking" than a 12-point plan or anything like that. There are a few things that can effect change in organizations, and I focused on the two that I could impact most immediately: people and values.

For the former, I had the mandate to basically build a new staff;. That's an enormous advantage that not every new design director gets when taking over a new team. There's a truism in political circles that "personnel is policy," and I always liked that idea. If you get the right people in place, everything else becomes much easier.

For the latter, that was made a lot easier once I'd started to establish a foundation of "the right people." But there was also a campaign necessary to educate the organization about how digital products are built, and that was a big part of my job—talking to stakeholders, making presentations, bringing in best practices and speakers etc. That was basically my day-to-day involvement; having the right conversations or introducing the right ideas to help shift the team towards the kind of values that we thought were important.

@Min: Great to hear from you. Thanks for the questions.

1. Well as a kid I was always into art and thought I wanted to be a painter or illustrator, so I went to art school with that goal in mind. But while I was there I tripped into graphic design and realized those were the problems that interested me the most, and that led me to doing design professionally.

2. I'm very passionate about doing graphic design but I really didn't like doing print design. So the web was the perfect alternative; I could use (most of) the tools of traditional graphic design but in an environment that was much more immediate, and a lot more forgiving in terms of mistakes. As the web matured and designing things became not just about layout but about behavior and making systems, I just got more and more engaged. I consider myself really lucky that I found the right calling!

@Kimberly: I'm not sure these are my top three best ever things, but they're certainly among them.

• Being professionally happy has less to do with what actual work you're doing than it does with genuinely liking the people that you work with —including yourself
• There's nothing better or more valuable than being in charge of your own time. Having a spectacular, well-paid design job that entails constant meetings and travel doesn't hold a candle to being able to hang out in a park on a spring afternoon anytime you like.
• The job of a designer changes every five years. It's very hard to plan for that kind of thing, but knowing that change coming is a huge advantage.

I'd be remiss not to mention that there are tons of similar insights in my new book!

@Celine: Yes, still answering questions! What's most interesting to me today is evolving the way we access the information that's relevant to us on mobile devices. We're still just in the first decade of this, and there's still so much further to go. This also happens to be the problem that we're working on at Wildcard—trying to figure out a "third way" between native apps, which offer the best user experience on mobile but are inconvenient to access, and the mobile, which has tremendous breadth available at an instant, but is a pretty terrible user interface. So deep linking, cards, the portability of rich functionality—all that stuff I find really fascinating. And it's only going to get more interesting too with new devices like Apple Watch and Android Wear and whatever else comes along in the next few years. Our current models for how we use mobile computing are going to change dramatically before this decade is out.

@MH: I want to say "You've got to have a balance of the two." But that sounds glib. Maybe I can give you a more insightful answer if you can give me a specific example where a designer has to choose between one extreme or the other (or find the right balance)? For what it's worth, I admit to being a pretty conservative designer (though that doesn't describe me politically).

@Nir: I'm not sure where that idea came from to be honest. But I think about getting the most out of the least quite a bit. When I was at the Times I talked a lot about trying to achieve "a maximum of elegance with a minimum of ornamentation," which not only fit the Times brand really well but was an extension of my whole approach to design. After all the name of my site has been Subtraction.com—a kind of obvious nod to minimalism—for a long, long time.

@Jacob: Not a dumb question at all. I'm obviously a big believer in using grids; I tend to feel lost when I'm not using one. But I'm not really dogmatic about whether everyone needs to use one or not. I tend to think that what works for you, works for you. That said, I rest assured in the knowledge that even if a designer thinks he or she doesn't design with a grid, they really are. A grid isn't just a tool for designers; it's a subconscious expectation that the audience/reader/user brings to any design solution. So whether you say you do or not, you're still using a grid.

I'm curious to hear: when you say that you encounter this frequently, are you actually meeting/working with designers who are actively advising you not to use grids?

@Anthony: That's a great question that I'm actually realizing no one has asked me before. I think the main reason I don't have my work up as an online portfolio is that it takes a lot of time—I think every designer would agree that putting together your own portfolio is one of the hardest design problems out there.

Also, I suppose I'm lucky in that I haven't really needed to get hired for work based on a portfolio in a number of years. That doesn't mean I shouldn't have a portfolio available; I probably should nevertheless. I guess I'm mostly just lazy!

That said, I do keep telling myself that I want to create a directory of all my projects over at Subtraction.com someday soon. Not quite a portfolio, just an index of things I've done that people can try out. One day.

@John: Thanks for the questions.

I spend a lot of time in Sketch. I'm a huge fan. Most everything I design, whether for native apps or for the web, starts there. I'll break out Photoshop or Illustrator to create assets for what I'm doing in Sketch, but I rarely do any actual UI design in those applications though.

That said, I'm doing more and more design with a product that I've been working on with Adobe called LayUp. It's an iPad app that turbocharges the brainstorming stage of the design process—there's a video at that link that shows how fast it can be to get an idea out of your head, onto the iPad screen, and then pushed off to one of Adobe's desktop apps. I use it to capture new ideas really quickly. The Adobe team has been phenomenal in building it, and I'm hoping that a public beta will be out pretty soon. It's starting to change up my workflow, and I think it will do the same for lots of folks.

As for what I spend most of my time on: Wildcard for sure. We bit off a huge challenge there, and there's tons of work to be done until we can say we're even halfway there. It's also the most fun of all my projects in the sense that I'm working with a great design team (my colleague Steve Meszaros and a freelancer) and a phenomenal engineering team. In fact, we're hiring another designer if anyone out there is interested.