Milton Glaser has been a force in design and publishing since before Inc. was around: He launched New York magazine with Clay Felker in 1968. He founded two studios that have produced some of the most iconic imagery ever put to paper, like the "I ♥ NY" logo. Fashion star Cynthia Rowley puts her whimsical visual signature on everything she makes. Though very different, they each exemplify in their work a trend that Inc. has charted for years: the rise of terrific design as a competitive business advantage.

In a conversation with Kris Frieswick.  

When did you realize you wanted to be in the business of design?

Milton Glaser: I knew that I was going to spend my life making things when my cousin came in to babysit for me when my parents were going out. He had a brown paper bag with him. We sat down in the living room, and he said, "You want to see a bird?" And I thought he had a bird in the bag, and I said, "Yeah." And he reached in and he pulled out a pencil. He drew a bird on the side of the paper bag. It was like receiving the stigmata. Suddenly, I almost fainted with the realization that you could create life with a pencil. And at that moment, I decided that's how I was going to spend my life. And as it turns out, that's how I have spent my life.

"Storytelling is so much a part of the visualization of any kind of finished product."Cynthia Rowley

Cynthia Rowley: It's crazy, but I have a very similar story, at least involving the same elements. In first grade, I went to a Catholic school, and one of the nuns said, "Draw this bird." It was a bluebird, so, of course, I drew something that was rainbow colored and everything. And they said, "No. You have to draw the bird." And so I tried again, and, of course, I wasn't drawing the exact thing. After the third time, I was so upset and distraught that I went home and told my mom. My parents said, "We don't want you to go to a school where you have to conform like that." They took me out of there and put me in another school. Because my dad was a schoolteacher and of humble means, my mom would cut open grocery bags and she would lay them all over the kitchen floor, after shopping, and that's what we would draw on.

Glaser: That's amazing. I mean, because grocery bags were our material of choice when I was growing up. That's what you drew on; there was nothing else in the house to draw on.

Rowley:  To me, a piece of white paper is almost a little scary. I like the comfort and the broken, blank plane of a brown paper bag.

There have been so many leaps in technology since your paper bag days. How do you think technology is affecting design in general and, more particularly, the type of work that you both do?

Glaser: Before we go too much further, let us agree on what design is, because you must understand that no two people have the same definition. Design is simply moving from an existing condition to a preferred one. That's it. It covers all cases. Nothing else is involved. Seemingly, our response to design has changed because our surroundings have changed, the environment has changed, technology has changed. Everything bears on everything else. So you cannot produce a change in technology without producing a change in design or a change in life itself. So one must assume that the nature of change is inherent in the nature of design.

"You cannot produce change in technology without producing change in design."Milton Glaser

Rowley: For me, storytelling is so much a part of the visualization of any kind of finished product. So, even when you look at a work of art, you feel there's some storytelling there. When I try to design something, whatever the end product is, there's some sort of story line there. We're thinking about the cultural Zeitgeist, and whatever that encompasses is usually incorporated into the ultimate design, but I don't feel like it's any different because we have technology. For me, technology is a great tool that can enhance things visually and the speed at which we can create things. I don't think it's anything that has changed my perception of design.

A lot of creative people lack business skills. How did you develop yours?

Glaser: I have no essential interest in business, and the details of business drive me mad. All I want to do is make things. But in order to survive in this world, you have to find a way of making those [things] and putting bread on the table at the same time. I've always been very fortunate. I've had wonderful partnerships with people. I've had people in my life who to some extent ran the business side of my life, or at least were partners and associates who thought in business terms much more than I did. And one of my rules of life is, always work with people you like. An essential part of being in business is trying to surround yourself with people whom you feel affinity for, or even more than affinity, affection. And I'm a great believer in that. I can't work with people I don't like; I can't work with clients I don't like.

"One of my rules of life is, always work with people you like."Milton Glaser

Rowley: I think I'm a very entrepreneurial person. I get really excited about it, and I don't know where it comes from, because in art school they told us, "You can't do the business. You're just the creator. You need a backer." I never understood what that meant; like, why would somebody give me money so I could have my ego massaged as a designer? Originally, out of necessity because I didn't have any kind of business partner, I started doing it myself, and I really love it. I didn't start out like that. I didn't want to have anything to do with it. I just wanted to make things. But then, if no one else is there, and you want your vision to get out there into the world, maybe it's the only way.

You've both worked in multiple genres. Cynthia, you've been quoted as saying you say yes to everything. How do you know when to say no?

Rowley: I have a hard time saying no, just because I spent my whole life hoping that people would ask me to do things. If I'm presented with something, I'm like, "Yes! Definitely." But if it's not something that is good for mankind, I won't do it. And I also think there are things that shouldn't really be designed. They're good the way they are.

Glaser: It's a good question. To some degree, it varies with your desperation. And the idea of doing no harm has always been essential to the work.

You're both so enthusiastic about your craft, but there had to be tough times, too. What have been the biggest obstacles that you've encountered along the way?

Glaser: Well, I've had a very extraordinary life. And I could say retrospectively that nothing was an obstacle, that everything I ever dreamed of came true. And it all seems easy, retrospectively. When [Clay Felker] and I started New York magazine, I would say for a year we didn't have any idea what we were doing. We put out issue after issue that was just terrible. We didn't know anything about how to write it, how to edit it, how to lay it out. And it took a year to begin to understand that, and we were lucky enough that people stayed with us without bailing out and disappearing. And after a year, we were able to build it back and make a magazine out of it. But I would call that a kind of benefit. It made you stronger, tougher, and you survived it.

Rowley: I liked that you asked us both that question and we both sat here with a pause, because I feel the same way. I don't feel like I've had a lot of obstacles. Of course, it's hard work--beyond hard work--but if there is an obstacle that takes you in a different direction, that means you think about something in a way you never would have thought of before. That's just life, that's just hard work, that's just the way it is. I don't feel like I've had any great obstacle. I feel really, extremely lucky and really happy.

Glaser: I've done my share of bad work, certainly, but what else is there except to fail and survive and go on?

"I think I'm a very entrepreneurial person. I get really excited about it."Cynthia Rowley

You both have said you feel like you're just hitting your stride. It's the last thing you would expect to hear from two people who could, with all justification, rest on their laurels.

Rowley: I think it's the underdog phenomenon. I've always felt like a little bit of an outsider. I have a lot of confidence, but I've never had the confidence to feel like maybe I've really succeeded, and I think that's what ends up driving me to go, to work hard and experiment and take risks. This makes it harder for me to realize, Oh, maybe this is going to work out for me. I do feel like I'm just getting started.

Glaser: I think in everybody's life there's a point at which you want to see how far you can go. And one of the signs that you haven't gone as far as you can go is a continued enthusiasm to do your work, and your work still is a source of great satisfaction. Not only as a vehicle for your position in the world, but simply as an expression of who you are, your own evaluation of the value of what you've done. And as I say, the fact that you can continue feeling that you have something left to express is a blessing.

To hear more from the conversation, watch the video below.