Dan Rubin is a designer, singer, photographer, barbershop harmony aficionado, philosopher, and polymath. He was born in Miami Beach, Florida, and still makes his home in the Sunshine State when not traveling the globe. He is improving the world through design.
You’re gonna be our guinea pig because you’re our first interview.
So, let’s get started. Describe your path to becoming a designer/photographer.
Uh, wow, how long do you have? (simultaneous laughter erupts)
I’ll try to keep it to the short version. By age 12, I was getting familiar with computers, doing a lot of art (oils, watercolors), and getting interested in typography. I didn’t know it was typography, but I was interested in letters and shapes.
Over the next few years, I learned more about computers and merged my understanding of color, depth, and perspective while using desktop publishing tools. I was lucky enough to know people who were involved in the internet very early on. Our neighbor had given our family a Mac and a friend of the family had a web hosting company. That was my first exposure to the web proper.
I was homeschooled by my mum, who was trained as a teacher at Cambridge University in England. With the time I put into computers, desktop publishing, the web, and art, in addition to swimming, scouts, and singing, I wouldn’t have had time to go to school. I wouldn’t have been doing homework.
By age 15 or 16, my parents encouraged me to get a job that would be intellectually stimulating. One of my advisors in scouts had just been named curator for a new museum for the Seminole Tribe in Florida and he needed an assistant. Normally this position would be for a college graduate, but I guess he had enough faith in me to hire me.
It was the most amazing experience. I was basically going to graphic design school by learning from magazines and books. I gave myself a crash course. I was a sponge. In a two year span, I had all the learning materials I needed.
At the museum, I was also asked to build an interactive exhibit which was the reason I started learning about interaction design and product design. I worked my tail off to build that interface. I was so proud. During that time, the web became something that people knew about.
I was lucky enough to have had a modem and internet access to do online research so I was learning about how to build for the web although I wasn’t actually doing that yet. But, my next suggestion was going to be, “The museum needs a website,” because the very first time I ran into the web, I understood how important it was going to be.
One night when I was running off copies for the museum, I drew a table based layout on this blue sheet of paper. On the other side, I hand wrote the HTML for it. When I got back to the computer, I typed it in and it made the thing that I drew on the other side. I thought, “I can create stuff. This is cool.”
It evolved from there. Until I was 16, my interests weren’t in technology. Actually, what I wanted to be was an aeronautical engineer. I wanted to do that and be a pilot.
All my interests merged during the years I worked as a contractor for the museum. That’s also when I started working for myself because they couldn’t hire me as an employee due to tribal rules. They had to hire me as a contractor. So I set up a company through my parent’s accountant and he said to me, “Yeah, you’re a sole proprietor at age 16.”
Over the next two to three years, rounding out the 1990’s, I started to do more and more web stuff because no one did it and everyone was interested in it. My intent was never to go into web design. I just kinda stumbled into it because it was there and I became a web designer before there was a term for it. I wouldn’t have discovered making things for the web without first learning print design. It wasn’t a clear path, but when you look back on it, it seems to make sense.
So was there an “aha” moment where you really knew what you wanted to do?
I don’t know if there was a single point. If there was, it doesn’t come to mind. There was no epiphany but that kind of ties into the way I was raised. The most valuable thing my parents instilled in my brother and me is that if we’re passionate about something, or even interested in it, we should just do it and let it run its course and if it’s something we learn more about and decide we’re not interested in, that’s fine, but we didn’t decide that prematurely. Instead of one big moment, there were a series of moments, and those continue. That’s an ongoing thing with me. I probably chase those moments, to be honest.
Was creativity a part of your childhood early on?
Apparently. My mum dug up this drawing last year that I had done in crayon and I couldn’t have been more than six. I had written out the alphabet, but it was clearly like I was writing out a typeface for her. Painting with oils and watercolors started around age ten. We were a musical family. I remember hearing a quartet sing live at a show and thinking, “I wanna do that.” So I did. And twenty-two years later, I’m still spending a lot of time performing a cappella. Reading was also a major part of my childhood. My parents’ house is full of books, as is mine. Creativity was a constant thread.
Did you or do you have a mentor? Who was it and how did they inspire you?
Good question. I don’t have one right now, not in the classic sense. As I get older, there are a lot of times I really wish I had someone 10, 15, 20 years older than me with experience to share. It’s tough with the web side of what I do because I’ve been around as long as anyone has. I can turn to my peers and that’s what I do. So I have a lot of mentors in small ways. Anytime I get a chance to talk to my peers and glean something from them, I do.
When I was younger, I did have a couple mentors that I owe a lot of my approach to various things to. The curator of the museum, David Blackard, was a key instrumental figure in my development at that stage. He was a little wacky, slightly nuts in that great way, and he played the role of a fantastic professor or teacher. He was a Native American historian and he knew facts about everything. He was completely willing to have faith in me and that was the best part of him being a mentor. A mentor doesn’t teach you in the educational sense. In the more classic sense, a mentor is someone you learn less specifics from and more of how to be, how to think, and how to react. They teach you how to be confident, how to ask questions, and when to figure things out for yourself.
There were a couple of guys in my singing life that were mentors in the same way. They were sources of encouragement and taught me about how to be a grown up in various situations that your parents can’t necessarily prepare you for. From ages 14 to 18, my swim coach was in that same role as far as going above and beyond in giving me the tools to find motivation within myself.
I’m much better off today than I would have been without any of those people contributing to me all around the same time.
I have one more to add, aside from my brother who’s a fantastic inspiration to me. By the time I was 18, I was working for myself getting paid by local clients for design projects and providing technical support. I tried to see how college would work. My English professor was awesome (he’d probably shoot me for using the word awesome). Now, I had never written a paper until I had that class, because I’d never had to. In one semester, he basically taught me about technical writing and editing. I didn’t think it would be terribly useful until I started blogging and writing. I owe all of that to my one semester with Professor Burks. I’m not sure where he’s teaching now, but if I ever find him, I’m giving him a copy of both books I’ve co-authored.
Tina: I have a question. Where were you born?
Miami Beach, Florida.
Ok, but your mum’s from England?
My mum was born and raised in England. My dad was born and raised in Brooklyn and Mt. Vernon, NY. He found his way down to Florida in his early twenties, decided at random that he was going to start sailing boats, even though he didn’t know what he was doing. That’s a hereditary thing. (laughs) He started delivering sailboats from the East coast of the U.S. to Gibraltar, where he met my Uncle. On one of his longer breaks between delivering boats and heading back to the U.S., my dad was invited to stay with my mum’s family in England and the rest is history. My parents moved to Florida when they got married. So that’s where I was born.
A lot of people ask me, “Why are you in Florida? Why aren’t you in San Francisco, New York, or London?” It’s because I grew up here, and it’s not horrible. I won’t stay here permanently, but when you grow up in a place, you make a lot of connections. I’m close with my family. I run the studio with my brother, we sing together, and do all these other things together. And there are two international airports that allow me to travel easily.
“I feel a constant pressure, not to do any one thing worthwhile, but that everything I do should make a difference…I think that’s my favorite thing about design as a broad term. To me, design is the medium through which I can improve the world.”
Was there a point in your life when you decided to take a big risk to move forward?
Possibly, although a lot of what I’ve done could probably be considered risky rather than a sure thing. There have been a couple moments where I have consciously not taken a big leap forward. I guess the decisions I’ve made in turning down opportunities could be considered my biggest risks.
We’re gonna jump back a bit. You talked about some of your mentors and people who have supported you. Who has encouraged you the most on your creative path?
Um, it has to come down to my folks, ultimately. I don’t think I’ve had people in my life who aren’t encouraging, but the groundwork for all I do and who I am was established when I was young. They were enabling in the most positive ways, fostering and encouraging creativity. My family (Mum, Dad, Alex, and me), we’re the kind of people who recognize when someone is passionate about something and we will do whatever we have to do in order to encourage that person. I feel really lucky that I haven’t had any barriers, and because of that, I try to help others if I see someone who needs encouragement.
That’s cool. So then, do you feel a responsibility to contribute to something bigger than yourself and what do you hope to contribute?
I want to fix the world. I feel a constant pressure, not to do any one thing worthwhile, but that everything I do should make a difference. The only shame of it is that the drive to contribute to something doesn’t always result in me being able to do something. It isn’t always a clear path from, “I want to help, I want to make products that don’t suck, I want to fix every interface I see that’s difficult to use.” I think that’s my favorite thing about design as a broad term. To me, design is the medium through which I can improve the world.
Are you satisfied creatively? Where do you see yourself in five to ten years?
Are any of us ever satisfied creatively? I’m sure there are a lot of people that are satisfied, I just seem to know more people who aren’t. The minute that I feel happy with something I’ve done, I feel like it’s probably not good enough, there’s a problem, or I’m not trying hard enough. If someone else said that to me, I’d say, “You’re an idiot! It’s fantastic work. You should allow yourself to enjoy what you’re doing.” That’s one of the things I can’t internalize. It’s probably unfair but I don’t think I’d be where I am if I didn’t keep pushing myself. I don’t think there’s a point that I could reach, or that other creatives reach, where they say, “There, I’m done. I can create anything I want and it’ll be perfect.” I think it’s what leads me to try so many things. One interest leads to another and then another until it becomes a really complicated fractal.
As far as where I see myself in five to ten years, that’s an awesome question. More recently, I found an essay I’d written in preparing for my G.E.D. (as I was homeschooled and had to take adult education classes to prepare for testing). I wrote the essay when I was 16. It was about where I imagined myself in ten years. When I discovered it, I realized my head was in a very different place back then. It’s a curious exercise to look that far out. The older you get, the more you realize you have no idea who you’re gonna be several years down the road. You’re in very different headspaces. So I’ve been setting myself little 2 to 3 year goals.
Over the last 3 years, I’ve gotten back into photography. I love the process. It’s very cathartic for me as I travel to discover a city by wandering around with my camera. Since I want to be doing the things I love, I’d like to be earning a bigger percentage of my income doing photography. I’d like to do some coffee table books and have a few gallery shows. That’s one of the (many) things on my list.
I’m also interested in wayfinding and environmental graphic design, which tie into my interest in architecture and the planning of spaces. I’m interested in typography on signage. I’ll always be passionate about the web, but whether I’m designing for the web or print, it’s still interface design. There’s still an interaction. I want to make things better and easier to interact with. I want to do more things in the physical world that combine all my experiences. That would be fantastic.
The theme is still design. Still creativity. Though not just creation for creation’s sake. I’m very interested in creation for the sake of solving a problem.
Ryan: I like what you said about creatives not being satisfied. I think we have to learn to be okay with our discontent and allow it to pull us forward instead of bringing us down.
Yeah, that’s challenging. In life, there are moments that are going to constantly challenge us and we’re going to want to say, especially as creatives, “I don’t know how to design anymore. Who’s allowing me to do this for a living? I should be working at a fast food restaurant.” We all have those thoughts. They ebb and flow. It’d be dangerous if we lived at the positive end all the time because we would get complacent. We need those moments where we question ourselves and wonder whether we belong, whether we deserve the attention we’re getting, or the person we’re with. Those are the moments that teach us the most about ourselves. They’re the psychological and emotional equivalent of a snake shedding its skin. It might be painful. It might take months. It might be seasonal.
This reminds me of a video Zack Arias1 did about the same kind of feeling. It’s a reminder that even people who do fantastic work have moments where they look at everything they produce and they want to start over and find another line of work. It’s a human thing, but it’s especially a creative thing. I get my energy to overcome that by being reminded that the people I look up to also go through the exact same thing. It reminds me, “Oh yeah, that guy isn’t a superhero, he had a crap week last week and wanted to quit.” Then I can get back to work and stop freaking out.
This is all really good. If you could go back and do one thing differently, what would it be?
Only one? Oh, wow.
Yeah, we’re pulling out the deep questions here.
Yeah. I feel like I hear these questions all the time. Not to me, but you hear them. Any interviews I’ve done in the industry don’t really get to this stuff. These are important questions.
It’s funny. The first thing that comes to mind doesn’t have anything to do with design but you can chalk it up to regret. There was an opportunity my brother and I had around 2000. Through people we knew who worked at Disney, we were given the opportunity to do a six month cruise to sing in the quartet that would be doing the entertainment. It might sound funny but I really wish I would have done that. I don’t remember why I didn’t do it. I know now that it wouldn’t have made a lick of difference to anything. I turned it down for what ended up being arbitrary reasons. I don’t like arbitrary decisions.
If you could give one piece of advice to another creative starting out what would it be?
(long pause) I haven’t gone anywhere. I know the silence is unnerving because there hasn’t been much of it…
Don’t worry about the things that tend to consume our thought processes or that we tend to worry about. Just make sure you are doing things you are passionate about and working with people you want to work with who encourage you rather than worrying about things like cash flow, how you will do your accounting, and how you should send invoices. All those decisions take a lot of time and the fact is that they’re not that hard to figure out. You can ask people. You’ll make mistakes, but as long as what you’re focused on is what you’re passionate about, all the other things will fall into place. If there’s anything you’re going to give less priority to, it shouldn’t be your passion. You can never go wrong with that. If you have a bad day but you’re doing exactly what you want to be doing, it can’t really be that bad.
Okay, we’re gonna ask some lighter questions. We won’t make you think quite as hard.
How does where you live impact your creativity?
Oh, immensely. It’s an interesting challenge for me because I don’t love South Florida. I get little inspiration from where I live. I get inspiration from the places I go that aren’t here. I’m in a weird place where I’ve reached the realization that I need to be somewhere else because I get inspired by the energy of big cities like New York or London. Whether I would be able to concentrate in those cities is another question, but I’m dying to find out.
I’m not sure anymore that where you are and where you live need to be the same thing. I actually find sometimes that the lack of interest in what’s outside of these walls when I’m in Fort Lauderdale helps me be okay with being inside these walls working. I take advantage of where I am in that there isn’t much of a community here. Most of my creative friends live very far away. That works to my advantage sometimes.
It’s the same with Newcastle when I’m spending time with Naomi.2 She is the same in that she gets her energy from being in big cities. But being somewhere like Newcastle means there are fewer distractions. That’s not to say I don’t love Newcastle – I do. It’s important to have inspiration around you but also to find balance that allows you to have enough quiet to focus. The idea that you need to be in one place to be creative is too much of a constraint.
You mentioned Naomi. You’re both very creative people. Is it challenging to be in a relationship with another creative person?
We love working on projects together, whether for clients or personal projects. It’s good to have someone who you can trust and bounce things off. We’ve figured it out quickly and we respect that there are times when we each need alone time. We’re both similar so it makes it easier when you understand each other. You don’t feel jealous or upset about it. You understand why the other person needs that time alone. I love that it doesn’t have to be explained. It’s a huge benefit to being with someone who is creative. There are certain thought processes that we have as creatives. It’s just a different way of looking at the world and how you spend your time. Friends who don’t do creative stuff think I work all the time. I feel like I barely work. I try to make what I do not feel like work. It should feel like I’m playing.
All right, what does a typical day look like for you?
(chuckling) Uh, I don’t know if there is one. Ask me next week and it’ll be different.
Do you keep a regular schedule?
Yeah, I’m horrible at schedules. I can keep one when I have to. I don’t like being on a schedule. I don’t think things should be created on a clock. I didn’t realize that early on. It perplexes me why anyone would force a creative person to work on a schedule. Some of my most creative time is after midnight. I’ve always been a night owl.
I don’t have a schedule but I do have routines. I really like to read the news when I wake up. I would like that sentence to be, “I like to read the newspaper,” as I’m always staring at a screen. I would like my routine to involve more exercise and time outside doing something more basic, but that will come in time.
“In life, there are moments that are going to constantly challenge us and we’re going to want to say, especially as creatives, “I don’t know how to design anymore. Who’s allowing me to do this for a living? I should be working at a fast food restaurant.” We all have those thoughts. They ebb and flow.”
Current album on repeat?
I haven’t been listening to a lot lately. It’s a dry spell. Really strange. At the moment, I would say something by Sigur Rós. Normally it would be Collected by Massive Attack. Massive Attack has been my go-to music to get me in the zone. But if I’m learning music for my a cappella group, I can listen to it on repeat for days and days.
Do you have any favorite movies?
The ones that pop into my mind are Backdraft, The Dark Knight, The Fifth Element, and The Princess Bride, strangely enough. I also loved Inception. There’s another movie of Christopher Nolan’s – Following.3 I’ve found I’m a fan of Nolan and Danny Boyle. I like Memento as well. I could keep going…
Do you have a favorite book?
There are a lot. I’m a recent Neil Gaiman fan. His work is fun and twisted and just beautifully creative. A book he wrote with Terry Pratchet called Good Omens is one of my favorites. I’ve loaned it to so many people. It’s a toss up between that and Pattern Recognition by William Gibson.
Last question. Favorite food?
Oh, I am the pickiest eater on the planet. My favorite restaurant is probably going to be a nice little cafe somewhere in England. Give me a place that makes a really nice turkey and cheddar panini and I’ll be in heaven. But I can also never turn down pizza.
Mmmm, pizza sounds really good right now.
Now that I’ve said it, I kinda want it. (laughter all around)
I think we covered everything.
Man, this is tough. As we’re going along here, I’m picturing the mock-up you sent me and all I keep thinking is, “This is way too much material.”
That’s alright. You said a lot of really awesome stuff. We want to make this a resource.
If there’s anything good that can come from this experience, it’s that no matter who else you interview, this will be the longest one.
Haha, let’s see. We’re at 2 hours and 15 minutes right now.
Yeah, I guarantee it. Nothing is a simple A to B.
That sounds like that’s really the story of your life for the most part.
None of the stuff I’ve done would have happened if I’d lived it any other way, so I have to embrace it, as strange and weird and frustrating as it sometimes is.