Designing Useful Interfaces

Designing Useful Interfaces
January 24, 2014
In this Office Hours session, Jason Santa Maria explains his creative process, becoming a better designer, working with type and and how he stays productive. Jason Santa Maria is co-founder and creative director of the collaborative writing platform Editorially.

N.B. This is the unedited live chat transcript.

Joseph: Will you talk about the process of designing the whole Editorially app?

From a visual standpoint, everything starts out with conversations and sketching. We have a huge wall painted with that white board paint in the studio, so I usually draw stuff out on there. I can stand up there drawing on the wall all day. From there I move into some combination of Illustrator, Photoshop, and code. And we just keep testing among ourselves and a small group of beta folks that we know. And iterate until things feel right.

Joseph: How big is the team?

There are 6 of us, and a few contractors for support and testing.

Dave: So that first part is collaborative? On the Whiteboard wall?

Yes, though everything is collaborative That’s the way I prefer it, but it’s also easier because our team is a manageable size.

Miguel: How far do you go on the code/prototype?

It depends on the interaction. Most stuff you can judge by just seeing static images. Other things you need to see how it will load and interact with the rest of the page. The new sidebar menu for instance, we needed to prototype pretty heavily in code. Because it affected the layout of the rest of the app, the text, the other panels, etc.

Philip: Do you have everybody on-site or do some of the contractors work remotely?

We have three folks in NY, everyone else is in a different city. We spend all day in Slack (previously we used Campfire), and have standup calls everyday on Google hangouts.

Miguel: Are animatics part of the process or are they usually done when everything is built?

We don’t typically do animatics. I’m pretty good at talking my way through stuff with sketches or examples from other places. Plus, as the app move ahead, it becomes easier to reuse things or relate ideas back to what you’ve already made

Christine: As a web developer and illustrator, I’m obsessed with the big images. Any advice for incorporating hand-drawn letters and images in webwork? I’m trying to redesign my website, and want to incorporate hand-lettering and hand-illustration. And looking for approaches and advice.

That’s awesome. Do it! Well, the best part about hand lettering is that it can be totally YOU. It doesn’t need to look like anyone else’s stuff. As for advice, just scan stuff as large as you can. You can do a lot by scanning in as bitmaps so that you can easily isolate the artwork

Miguel: How do you view design trends such as flat design, parallax and side menus?

Trends are kind of shit, IMO. Design needs to serve a message. Style isn’t design.

Josep: Keith Rabois (Square) stated that “the web is dead” and that he only believes in business built on apps. What do you think about this? I think it’s interesting from the point of view of design too.

Bah. That’s a limited view of the web. Maybe apps are where money is right now, but we all know that the web is a gigantic place. I mean, how often do you encounter a corner of the web where there is a community around some random thing? The web is very much alive in more places and more ways than any of us can grasp. And that is a wonderful thing.

Miguel: Are there certain times or places where you’re most productive/creative?

Good question! I like to think I can be productive anytime, but I’m coming to realize that I’m best off in the morning. I miss when I was younger and I would work into the late hours of the night. That doesn’t seem to happen so much anymore. One thing I’ve discovered more recently is that I love writing on train trips. The east coast of the US is really well covered with train lines. So some days I would take a train three hours in one direction, eat lunch, and then come back. And just write the whole time. The rhythm of the rails was perfect for writing. I’ve gotten better at figuring out how to approach problems or ask for help when I need it, so it’s mostly about time these days.

Dave: We have a lot of visuals (photos, illustrations, videos, etc) to try and tell our client’s story. Understanding how the copy supports the visuals and how the visuals support the copy can be challenging for us. Do you have a process or strategy for approaching that kind of a problem? For example, we could spend a lot of time working on some copy and then when it comes to laying it out, we find the header would look better short and punchy, or this paragraph might be better if it was shorter and to the side of this video. That sort of thing.

Unfortunately, I’ve always found that you kinda have to start making the thing sometimes in order to figure out what’s working. Planning can only take you so far. But, having a good content person on the team makes a HUGE difference. I’ve had the good fortune to work with a lot of great writers and editors in my career, and they are almost always the most important person on our team (IMO).

George: Are there any common mistakes you see young designers make? Do you have any advice on helping them find their own style?

Yes, and I’ve made a bunch. Ego is one of the biggest I think. Design school made me feel like I should get out there and get a huge job. I really didn’t understand the idea of paying my dues. But that lesson was learned pretty quickly.

William: Paying your dues in what way?

Well, you might know how to use tools and make stuff, but you don’t have experience in life, in work, or with real projects. That just takes time.

Also, one of the best things young designers should know: Don’t rush to be out on your own. You only have so much tolerance for learning in life, and it’s SO much easier when you are younger. Go work under someone smart and soak up as much knowledge as you can. That stuff is really tough to learn on your own later.

Ceasar: How can designers develop a tasteful typography pallet? My guess is it comes with time and experience but with so many choices made available, should we stick to a select few? What resources do you recommend that we refer to frequently?

Yep, time and experimentation is where it happens. It’s a skill that just takes time to develop.

But! Don’t feel like you need to use new fonts all the time. Find a few that you like and keep working with them. You’ll find it’s easier to learn about type if you constrain your options and palette for a while. Discover all you can about the strengths and weaknesses of a few good fonts.

George: I find myself self-conscious with my work, do you ever have that feeling?

Every day. We call that “imposter syndrome”. I don’t think that ever goes away. Or I hope it doesn’t. It would mean something bigger is probably wrong.

Miguel: Why do you design? What is your reasoning and motivation for what you do?

Good question. I think my answer may have changed over the years. At any given time, it’s been: I like to make things. I like to help people understand things better. I want to try and make the world a little nicer. I love typography. That stuff, mostly.

Philip: Are you a perfectionist? How does that affect your process? Does it slow you down? Is it controlling you or are you handling it and restraining yourself and letting it go when you know you can afford to be perfectionistic about your work, process and implementation of your designs?

In my head I always told myself I was a perfectionist. I said that to a friend once and he laughed at me. He said, “You get stuff out there, a perfectionist can’t do that”

And I guess that’s the thing. I know people who can’t put things out into the world because they can’t “finish” something. Perfectionism is debilitating.

Dave: Favorite To-do app/solution?


George: How do you feel about common fonts? For example – Proxima Nova is beautiful and works in so many situations but is it a “cop-out” to use? Would you experiment with something else just for the sake of freshness?

I don’t think any typeface is a cop out, save one maybe Helvetica. But yes, overuse of a typeface can water it down. Remember when everything was set in Verdana and Georgia? They are some of the most beautiful screen fonts ever made, but we just saw too much of them. Proxima Nova is used a lot because it is plain and really sturdy. So it can represent lots of things.

Christine: What are you currently reading?

The line edits for my typography book.

Miguel: How do you overcome “designer’s block” or when having tunnel vision on a project?

It’s a typical answer, but I always go for a walk. It helps every damn time.

Dave: Any thoughts on Responsive design? Has it changed the way you approach a design? Do you always think about how a design is going to break down to smaller widths? And can that be almost paralyzing?

It’s flippin wonderful! It’s difficult for some things, but honestly I find it liberating. RWD makes content the focus more times than not, and that means text. That’s right in my wheelhouse. The only thing I struggle with are images.

Miguel: What’s your current method for solving images on RWD?

I’m still finding my way. For the A Book Apart site, I did double sized jpegs at high compression. And sized down. I like that approach because it’s still just a simple image call. But it’s for a crummy image. Now I just try to make everything be SVG. For the Editorially marketing site we did two separate images, one for normal screens and one for Retina. But I feel defeated making sites like that. Not sure why.

Kevin: In your last CreativeMornings talk you talked about saying no more often. Would you be able to talk more on how it’s been since then? Has your stance changed or grown stronger?

Definitely just gotten stronger. That’s one of my favorite things I’ve put out into the world. I felt really strongly about taking control of my time and what I bring into my life.

George: What are you favorite sources of inspiration?

Music, film, video games, books, newspapers, photography. All typical stuff. I try not to draw too much influence from other sites. That’s how people just started mindlessly making everything flat.

Kevin: Any up and coming designers (or even well established ones) that you’re jealous of?

I’m jealous of any really great letterers and type designers. It’s a skill I just don’t seem to have. Also, people who are good at logos. WOW, are logos so hard.

Aaron Draplin is one of the best in the world.

Maurice: Jason, what advice would you have on finding design mentors? For example, I interview a lot of designers (some who went to art school, some who didn’t), but lack of mentorship in the field seems to be a common thread.

Ooof, I’m not sure. I do agree, it’s tough and we don’t have a lot of that in our industry. I’ve mentored people in the past, but they just happened to reach out to me and I agreed. It’s not something I do much of because it is really time consuming, and I can’t always afford to, unfortunately.

Dave: Do you feel that writing has had an influence on you as a designer?

Yes, definitely. I struggle with writing more than I do with design, for certain. But it helps me understand what I think. Sometimes I don’t really know what I think about something until I try to write about it.

I think I struggle most with the mechanics of writing. I’ve never been great at tenses and differences between words (that vs which), etc. No matter how much I read about those topics, it never sticks in my head. I just try to be friends with as many editors as I can find!

Akshat: Any must follow design blogs ?

I like Colossal and of course Swiss Miss.

Kevin: I imagine you’ve dealt with burnout on at least one occasion. Do you have any tips on overcoming burnout?

I have! When it’s happened to me in the past, I try to change things. That’s easier said that done, but change things that you can easily. Things that don’t hurt anyone or leave you unable to make rent. When I was feeling burnt out a few years back, I started expanding what I did into other things to try on some different hats.

I took a job at a startup, started teaching a class, started a book company, and took up sewing. All were new things to me but helped give me some perspective on what I wanted in my career.

Paint stripping an old mirror yesterday and sewing pillow cases today. Weekend projects!

Three new pillow cases complete! So happy to have a sewing machine again.

Josep: Wow! Interesting! I’m starting an apparel company that will launch in a few weeks, so I’m pretty curious about your opinion: what do you think about fashion?

I wish I had more of it! Or at least more time to invest in it.

Joseph: In web design and industrial design, for example, designers are aware that the first is the function, the purpose, and style follows. But the fashion world seems disconnected from that message. And it’s particularly interesting because designing apparel is one of the first fields, perhaps with architecture, in which humans began designing.

I like fashion that can be really functional and beautiful. And I like a lot of what’s been happening through Kickstarter, some more bespoke projects to make pieces of clothing the best they can be. I got one of those 10-year hoodies and love it. Granted, that won’t be winning any fashion competitions.

Miguel: Where do you see the design industry shifting in the next year?

Not sure, but I’m scared of all the Net Neutrality stuff happening right now.

Philip: Thoughts on iOS 7?

Interesting, but seriously half baked. Some thoughts on that here.

Julian: What do you think is the best way to learn and get started in this industry? Formal training (design school), self taught, mentorship, etc. I’m currently working for a company but have no formal training. I have basically just learned most of this stuff on my own and on the job. I am at a point where I want to move on and expand my knowledge. Where should I go from here?

I think self-taught is OK if you don’t have other options. Otherwise, a class room setting or mentorship is best. You need to not only have someone with expertise to help show you good and bad choices, but also be in an environment to learn from your mistakes and successes.

This is best in a classroom because you can learn from your successes and failures, but also all the ones from your classmates. It’s like being in a incubation chamber.

William: Thank you so much for doing this Jason.

The pleasure was all mine.



Welcome to Dorm Room Tycoon

Interviews that cut to the chase and extract wisdom. Learning from the most influential innovators. Hosted by William Channer.

Wisdom from all my heroes.
Derek Sivers

Join our world

Follow us on Twitter, subscribe on iTunes or SoundCloud and enter your email below to get new interviews.

The goal

To help you build a successful startup that solves a big problem in the world.


Get in touch

Email: to give feedback or to sponsor.