Dan Cassaro is a graphic designer and illustrator living and working in Brooklyn, New York. He runs his own design shop, Young Jerks, and spends his free time using typography to make words accountable for themselves.
Dan has a way with words and a style all his own. Over the summer, he and girlfriend, Niamh, set out on a road trip in their kick-ass Scout and gave us a serious case of wanderlust. Dan’s been home for a few months and shared with us about his transition back into full-time freelancing, his most memorable experience on the road, why the power of typography shouldn’t be underestimated, and his thoughts on being discontent.
Interview date: November 7, 2011
Describe your path to becoming a designer.
I didn’t always know that I wanted to be a designer—it happened much later for me. I was 23 when I went to school for design. I always knew I wanted to do something with the visual arts. After high school, I did a couple semesters at Alfred University, which is a fine arts college way, way, way upstate New York and as far away from Manhattan you can be while still being in New York. I think I was scared to go to art school in Manhattan. It didn’t really work out. I wasn’t ready and didn’t really know what I wanted to do. I think I had a lot of hanging out left to do before I could make any important decisions about my life.
I left college and moved around after that. There was a long period of time where I was waiting tables and figuring out what to do with myself. I lived in Connecticut and Savannah before eventually moving back to New York and going to the School of Visual Arts (SVA).
Even then, I think I went to design school on a whim; I’m not sure I even knew what graphic design was. Eventually, I fell in love with letters and typography and now it’s all I think about.
You already touched on this in the first question, but did you have an “aha” moment when you decided design was what you wanted to do?
I think I had an “aha” moment about what I was going to do within design because design is so big—you can do anything. You can lay out magazines or be a typographer or be more of an illustrative designer. I remember at SVA when I had my sophomore portfolio review and the head of the department wrote a comment that said, “Your strength is typography.” Typography was something I had never specifically considered, but I had always enjoyed it just as much as everything else. I thought, “Someone thinks I’m good at this. Maybe I should try focusing on it.” Now I’m obsessed with it. I think I can trace it back to that moment when I chose to go in that direction.
We heard that you have a crazy story about design, smoke coyotes, Paul McCartney, and the desert? What’s that about?
Yeah, that was the moment I knew design was in my BONES. A few years ago, I went to see Paul McCartney at Coachella. There are thousands and thousands of people that go to this thing, so if you want to get up close for a headliner, you have to work your way to the front early in the day. My friend and I went right up front as soon as we arrived and then just waited there for seven hours. I’m not exaggerating either—seven hours, packed like sardines in the hot desert sun!
After the show, we were driving to our motel, which was out in the middle of nowhere in a tiny town called 29 Palms. To paint the picture, I was driving through the desert at 3am, totally depleted, in a stupid rented white Mustang convertible. I was completely dehydrated and geeked out on Paul McCartney. It was really surreal.
And then, I started hallucinating coyotes. I was dead sober by the way; I had a beer maybe eight hours prior. It’s funny though… I knew that I was hallucinating because the coyotes were made entirely out of smoke. And all I could think was, “I can’t tell my friend about these ghost coyotes or she won’t let me drive.” So I just drove and stared at these smoke coyotes in my headlights for a half hour or so.
They were really nice looking, all modern and pointy. They looked like Charley Harper had designed them or something. Afterwards, I had a funny realization about how deeply design is embedded in my brain. Somewhere in my subconscious, I was art directing my own hallucinations. It makes me feel like I am in the right profession.
Right on. That’s a pretty wild story. How long have you been doing freelance?
It’s been on and off. I graduated about four years ago and spent two years of freelancing doing mostly motion graphics. Then I took a full-time job at MTV for about a year and went back to freelance this past summer. But, this is the first time I feel like I’m freelancing with intent and trying to build myself as a company and think about the future.
This past summer you took a trip with your girlfriend, Niamh, across the United States.1 What was the motivation behind that and how did it go for you guys?
That was my victory lap for quitting my job (chuckling). My relationship with my girlfriend has always been based on traveling. When we were first hanging out, we travelled all the time and we’ve tried to take mini road trips every year. The only issue is that both of us are pretty romantically involved with our work too so it can be hard to reconcile both of those things. Six months before we did this trip, we hashed out a plan to try to work and travel at the same time. What she does lends itself to traveling—she’s a scientist. She has to do research at different field sites and a lot of them are on the West Coast. We figured I could freelance and she could work. The Internet is everywhere, so I just thought, “Why aren’t we?”
Part of the inspiration came from when I worked on the Fifty and Fifty project with designers from across the country. I got to learn about different places and introduce myself to people all over the U.S. and then get totally bummed out because I was sitting in the same chair every day and not seeing any of these places. I wanted to be able to go and see all those places firsthand. That’s where the idea came from.
[Tina] When you were traveling this summer, what was your favorite place?
Definitely the Grand Canyon. I think people might assume that it’s overrated, but it’s totally not. It’s the coolest thing ever. I got choked up when I saw it. Ron Swanson2 says it’s one of the few places it’s OK for a man to cry and I totally agree. I thought we would show up, look into this hole in the ground, and walk away, but we spent three days there hiking. There was something about it that was extra special and really magical. Have you been there?
No, but it’s on our list of places to visit.
You gotta go! You should drive there tonight (laughing).
Grand Canyon Village is located in the national park so there are no private businesses there, but I guess there were some lodges there before it was a national park. These places are little time capsules in the village and are completely untouched by time. One day, we hiked all day and stopped at this lodge to sit on the porch and have a cocktail while we watched the sun set over the edge of the Grand Canyon. It was amazing.
[Tina] Did you have any realizations while out on the road traveling?
The biggest surprise was that traveling was like a full-time job. We spent most of the day thinking about which route to take and where we would sleep that night. We never planned more than a day or two in advance—not because we were being cavalier, but just because we couldn’t. A lot of the time was spent figuring out logistics. It was fun and exciting, but definitely a full-time job.
We got really good at breaking down the camper and figuring out how to back it up, which was super hard. It was nice seeing the progression of what dunces we were with the trailer starting out and then by the end we were backing it up mountains and setting it up for the night at a RV park in complete darkness.
We saw new stuff every day. What’s cool about driving across the country is that the scenery changes so fast. We had to pinch ourselves and remind ourselves how amazing everything that we were seeing was. We were seeing beautiful stuff constantly and tried to take it in and stay floored the whole time.
Was it hard coming home to Brooklyn and getting back into the normal routine?
No, it wasn’t hard. We were out there for two and a half months. We had spent a lot of time away and I was ready to get back to design full-time. I missed Brooklyn and wanted to come home and see my family and friends and eat good pizza. I love Brooklyn. It was easier to come home because I wasn’t coming home to the same place I left—I had quit my job and hit the road and was coming back to a whole new thing where I was going to be freelancing. I think that helped me beat that post-vacation depression.
Do you still have The Scout or did you sell it?
Oh, no, I have it. I’ll never let it go. My parents are allowing me to store it in their garage. There was a section of the garage that had a bunch of my crap in it and they said that if I cleaned it out, I could store the camper there. We brought The Scout back and spent all day cleaning it and making it beautiful. We’ll probably take it out again next summer. I miss it already.
Jumping back a bit. Where did you grow up?
I grew up in Long Island about a half hour outside of New York city in the small suburb of Garden City.
Was creativity a part of your childhood?
Oh, yeah. I did lots of drawing and painting. I also wrote a screenplay when I was 12 years old. I just rediscovered it recently—you know, you go home to your parent’s house and start digging through all of your old shit. I came across this stapled looseleaf and thought, “Oh my god, I wrote a screenplay.” It’s terrible and painful to read. It bummed me out a bit though because, at that age, I think there was a lot of creativity going on and I had no inhibitions about what I was going to do with it, so I tried to do everything. It made me miss that optimism. I don’t think I am going to be writing any one-man plays anytime soon, but it definitely inspired me to try some new things.
Who do you think has been the most supportive of you along your creative path?
I guess it’s been my family. My friends are super supportive in different capacities, but my parents have always been supportive of me doing this, even when I was younger and didn’t realize it. They’ve always been my biggest fans, which I’m appreciating a little more now that I’m older.
Do you feel a responsibility to contribute to something bigger than yourself?
Totally and more-so recently as I gain more experience in design. I’m more interested in the unique powers that graphic design has and what we can do as designers. Designers have the power to have their voice heard through their art or assist in having other people’s voices heard. I think there’s a special thing we can do with typography and illustration—it’s a gift and not everyone can do it, so it’s our responsibility to be aware of what it can do and consider how we use it. I gave a talk recently where I spoke about the unique power that illustrative typography has—how we can rescue old ideas or words and make people consider them in a new way. It’s a megaphone for information and it shouldn’t be underestimated.
Are you satisfied creatively?
I am more satisfied than I’ve ever been creatively, but I’m not satisfied. This is why I like the name of your site—The Great Discontent. I think the reason I do this, the reason we do this, is that we’re all fucking malcontent; we’re all sort of unhappy. I mean, I’m super happy with my life. I have a positive outlook and try to have a sense of humor about stuff, but I’m perpetually discontent with everything, which is what keeps my work going. I am more satisfied with my work than I’ve ever been, but that discontent is the huge driving force. It’s what keeps me up at night and makes me work harder.
Where do you see yourself in 5 to 10 years? Are there things you’d like to tackle that you haven’t had a chance to yet?
Yeah. I don’t have a five year plan, but I do want to try a lot of different things. I’ve been thinking more and more about what’s going to happen in 5 to 10 years considering that I don’t want to be sitting in my basement as a freelancer trying to solicit work when I’m 40 years old. But, I don’t know. We’ll see.
You mentioned art a few times. Do you also paint?
Not as much as I used to. I just painted a mural at the Ace Hotel3 which made me miss making things with my hands. But when I’m my own client and doing things with typography, that feels like art to me. I do a lot of screen-printing and personal stuff that I don’t put on my website.
If you could go back and do one thing differently, what would it be?
I don’t know. The cool answer is to say that everything I’ve done has brought me to where I am today and I wouldn’t change anything. But, I think I would change some things: I would be a graphic designer sooner, I would have travelled more when I was younger, and I think I would’ve been nicer to my parents when I was 18. But, since I wouldn’t want to throw a monkey wrench into where my life is headed right now—I feel pretty good about it—I’m gonna go with my first answer and say I wouldn’t change anything.
Was there a point in your life when you took a big risk to move forward?
I think moving back to NY and going back to school was a risk or at least a big decision I had to make. It’s big for people in our generation who seem to have a hard time making decisions and buckling down. You know, forcing yourself to try and live up to the potential you probably have been hearing about your whole life. Deciding what to do and sticking with it was a big step for me. I had spent a lot of years floundering and screwing around without being committed to any one thing. It did pay off for me once I made that decision and stuck with it. I think that’s what being an adult is.
“I’m perpetually discontent with everything, which is what keeps my work going… It’s what keeps me up at night and makes me work harder.”
Was it a big risk for you to leave MTV and go back to freelance?
It was a risk because, all of a sudden, I had to worry about a paycheck. But, I had gotten to the point at MTV where I was working 9 to 5 there and also doing freelance work on the weekends. It was a relief to quit my day job and the transition into being able to freelance full-time was a smooth one.
If you could give one piece of advice to another designer starting out, what would you say?
Work hard at whatever you do and make it personal—don’t try to please this imaginary audience that’s out there because it doesn’t exist. I see a lot of designers pull inspiration into their work secondhand. Find the inspiration somewhere besides the Internet and do it for you. You can really tell when someone is personally invested in their work. If you’re doing work that you love, then other people are going to see that, and they are going to love it too. It’s as simple as that. Ideally, we all want to get paid for doing what we love, so we should push that if we can.
How does where you live impact your creativity?
It’s a huge source of inspiration mostly because there are so many people in New York doing creative things and graphic design specifically. There are so many talented people working here—it’s exciting and intimidating at the same time.
New York is so beautiful from a design perspective. It’s a real looker and it’s easy to find inspiration everywhere you go.
Is it important to you to be part of a creative community of people?
More-so recently. Working on some of the personal projects I’ve done over the past year, I’ve met a lot of people. Before this year, I only knew the people I went to school with. Through the Fifty and Fifty4 project and traveling, I met a lot of people and now it’s something that I value a lot. It was one of those situations where I didn’t know how nice it would be and now I really appreciate it. I have a ton of people whose opinions I really value and I can bounce ideas off of them.
[Ryan] Before you did Fifty and Fifty, were you connected with other designers throughout the states, or was that something where you got to meet them through taking initiative to do the project?
I knew some people and had planned to ask a few of them. The first 10 came easily, but after that it got harder. I had to dig and search people out.
What does a typical day look like for you?
I wake up at 9am and go get coffee. Sometimes I take a shower before I get coffee and sometimes I don’t. But, if I do not take a shower before I get coffee, then I don’t take one until 4pm in the afternoon. There’s a good hour and a half of answering emails and messing around on the Internet before I actually get down to work. I usually start work around 10:30am, take a long break for lunch to refresh, and then work pretty late into the night with a break in there for dinner. Lots of coffee, lots of cigarettes. Nothing too glamourous.
Current album on repeat?
I just downloaded The Beach Boys’ remastered version of Smile. I’m not a huge Beach Boys fan—more of a Beatles guy—but I’m super interested in the whole Brain Wilson myth. He’s bat-shit crazy and I think it might be contagious. If you listen to Smile too many times then you start to go crazy too. There are four discs to the album and tons of alternate takes of the same song. One night when I was working, I realized I had listened to different versions of the same 30 second harmony track over and over again. I had to turn it off and reevaluate my music choices.
Besides that it’s the standards—Wings, Springsteen, Warren Zevon.
Do you have a favorite book?
I keep re-reading Dave Hickey’s book, Air Guitar. He’s an art and culture critic and the book is a collection of his essays. Really smart and completely down to earth. I get more out of it every time I read it. Of all time? Still Life with Woodpecker by Tom Robbins. That book was kind of my bible in my early 20’s.
Hamburgers are my favorite food, but I’m kind of picky. There’s this hamburger renaissance now where everybody is opening up a hamburger restaurant in Williamsburg and other parts of Brooklyn, but nobody really knows how to make them! You get a lot of these fancy hamburgers that come out like meatballs and have a huge, hard bun that cuts your mouth and cost 15 bucks. So silly. Keep it simple: flat patty, ketchup, and a classic bun. Shake Shack knows what they are doing.
What kind of legacy do you hope to leave?
I don’t know. It’s hard to say what kind of legacy I can leave as a graphic designer.
I saw Aaron Draplin this summer in Portland and he referred to what we do as cake decorating, which I thought was hilarious and perfect. We’re not even making the cakes; we’re just decorating them. I don’t have any delusions that I am saving the world, but it would be nice to be thought of as someone who cared about the design work he did and didn’t take himself too seriously.
“If you’re doing work that you love, then other people are going to see that, and they are going to love it too. It’s as simple as that.”