Few things today are truly iconic, but the I♥NY logo is among them. Its beloved creator, the inimitable Milton Glaser — who also co-founded New York Magazine in 1968, and who is one of my most beloved creative and spiritual heroes — is an icon in his own right: often considered the greatest graphic designer alive, a remarkable educator who has shaped lives for more than half a century, a man of uncommon wisdom on art, integrity, and the kindness of the universe. In this beautiful and wide-ranging interview from The Good Life Project, Glaser offers an unprecedented tour of his magnificent mind and singular spirit. Transcribed highlights below.

On where the seed of his creativity originates:

I have no idea where it comes from. The thing that I do know is that after a while, you begin to realize, A) how little you know about everything and, B) how vast the brain is and how it encompasses everything you can imagine — but, more than that, everything you can’t imagine. What is perhaps central to this is the impulse to make things, which seems to me to be a primary characteristic of human beings — the desire to make things, whatever they turn out to be. And then, supplementary to that, is the desire to create beauty — which is a different but analogous activity. So, the urge to make things is probably a survival device; the urge to create beauty is something else — but only apparently something else, because, as we know, there are no unrelated events in human experience.

Glaser echoes Tolstoy’s timeless conception of art as a mechanism of human connection and Robert Henri’s notion of art as a brotherhood of mankind, reminding us that the creative impulse is integral to what makes us human:

There is something about making things beautiful, and we sometimes call that art, that has something to do with creating a commonality between human beings so that they don’t kill each other. And whatever that impulse is, and wherever it comes from, it certainly is contained within every human being. … Sometimes, the opportunity to articulate it occurs; sometimes, it remains dormant for a lifetime.

On his own unrelenting expression of that profound human characteristic:

I imagined myself as a maker of things from the age of five. I realized that to make something was miraculous, and I never stopped.

Recounting the formative moment in which he awakened to art, when his older cousin drew a bird for little Milton on the side of a paper bag and it suddenly came alive for the young boy, Glaser reflects:

I suddenly realized that you could create life — that you could create life with a pencil and a brown paper bag — and it was truly a miracle in my recollection. Although people are always telling me that memory is just a device to justify your present, it was like I received the stigmata and I suddenly realized that you could spend your life inventing life. And I never stopped since — at five, my course was set. I never deviated, I never stopped aspiring or working in a way that provided the opportunity to make things that, if you did right, moved people.

On how being the “class artist” in his childhood, constantly creating on-demand drawings for his friends, shaped his sense of purpose and belonging:

I always saw myself as being a facilitator of other people’s needs, in that very primitive way. I liked the fact that I had status, I had a position in life, and I could also be of service. … That designation was a useful one to me in terms of developing my own sense of who I was.

The story of “how 20 seconds can change your life” he relays at 12:22 is an extraordinary testament to the power a single moment of kindness has in profoundly changing another human being’s life:

When I was in junior high school, I had the opportunity to take the entrance examination to either Bronx Science, which is a great New York school, or the High School of Music and Art, another great school. … And I had a science teacher who was very encouraging for me to enter into science — I was very good at science — and he wanted me to go to Bronx Science. And I was evasive about that, because I didn’t want to tell him that it ain’t gonna happen. But the day of the entrance exam — they occurred on the same day — I took the entrance examination to the High School of Music and Art. And the next day I came into school, he was in the hallway as I was walking down, and he said, “I want to talk to you.” I said, “Uh-oh — the jig is up, he’s going to find out I took the ‘wrong’ exam.” He said, “Come to my office… Sit down.” And, as I was sitting there, he said, “I hear you took the exam for Music and Art.” And I said, “Um, yes.” And then he reached over, and he reached into his desk, and he pulled out a box of French Conté crayons — a fancy, expensive box — and he gave it to me, and he said, “Do good work.” I can’t tell that story without crying, because it was such a profound example of somebody — an adult, authority figure, sophisticated man — who was willing to put aside his own desire for something, his own direction for my life, and recognize me as a person who had made a decision. And he was, instead of simply acknowledging it, encouraging it with this incredibly gracious and generous gift. … The thing about it that always astonishes you is that moment — it couldn’t have taken more than two minutes — was totally transformative about my view of life, my view of others, my view of education, my view of acknowledging the other.

Echoing Joss Whedon’s fantastic Wesleyan commencement address on embracing our inner contradictions, Glaser reminds us that the art of life is not in choosing between opposites but in reconciling them:

You learn more and more that everything exists at once with its opposite, so the contradictions of life are never-ending and somehow the mediation between these opposites is the game of life.

Much like philosopher Daniel Dennett argued that “the chief trick to making good mistakes is not to hide them — especially not from yourself,” Glaser counsels that the first step to making better life choices is acknowledging the bad ones you’ve made, and drawing cultivates mindfulness and the essential art of seeing that doing that necessitates:

The first step is always, in the Buddhist sense, to acknowledge what is — and that’s very hard to do. But, incidentally, drawing — and attentiveness — is one of the ways you do that. The great benefit of drawing … is that when you look at something, you see it for the first time. And you can spend your life without ever seeing anything.

On how welcoming the unknown helps us live more richly and why we should try to, as Rilke put it, “live the questions” and cultivate the “negative capability” that Keats insisted was essential to creativity:

I can sound as though I know the answers to these things — I don’t know the answer to anything. You have to constantly be attentive to what you deflect in life, and what you pay attention to, and all the things that you can’t see, and all the preconceptions that you do have about everything. Those preconceptions basically blur your vision — it’s very hard to see what’s in front of you.

On how technology is changing us:

Everything changes everything. There are no independent events. … The virtual world has created a very different kind of nervous system for people who spend their lives in that world. And it produces different sets of appropriateness — of time, of morality, of ethics, of behavior. … [But] we don’t know what this is doing to the human psyche or the human behavior or any of it — we know it’s changing, we know it’ll be a profound change and it won’t be what it was, but we don’t know what the nature of that will finally be. It will probably have some benefits and significant drawbacks, but it is just emerging. [We] are creating a new kind of person.

On how we can ensure technology enhances rather than enslaves us:

The computer is dangerous because it shapes your capacity to understand what’s possible. The computer is like an apparently submissive servant that turns out to be a subversive that ultimately gains control of your mind. The computer is such a powerful instrument that it defines, after a while, what is possible for you. And what is possible is within the computer’s capacity. And while it seems in the beginning like this incredibly gifted and talented servant actually has a very limited intelligence — the brain is so much vaster than the computer. But, the computer is very insistent about what it’s good at, and before you know it — it’s like being with somebody who has bad habits, you sort of fall into the bad habits — and it begins to dominate the way you think about what is possible. … [Counter this] by doing things that are uncomfortable for it to do.

On always harnessing the gift of ignorance and never ceasing to expand oneself:

Professional life is very often antithetical to artistic life, because in professional life you basically repeat what you already know — your previous successes. It’s like marketing — marketing is the enemy of art, because it is always based on the past — not that art is always based on the future, but it’s very often based on transgression. So when you do something that basically is guaranteed to succeed, you’re closing the possibility for discovery.

Reflecting on art education and the cultural tension between art and business, Glaser adds to history’s finest definitions of art:

You have to separate making a living … from enlarging one’s understanding of the world, and also … providing an instrumentality for people to have a common purpose and a sense of transformation. … That is what the arts provide — the sense of enlargement, and the sense that you haven’t come to the end of your understanding, either of yourself or of other things.

Echoing Maira Kalman, who herself echoed Freud when she said that “in the end … it’s love and it’s work — what else could there possibly be?,” Glaser ends by reflecting on the meaning of life:

The things that I think are important [for a good life]: the friendships that I have with people I love; a marriage that has endured and continues to endure; teaching, which I’ve been doing for well over half a century; and feeling that whatever you know has a possibility of being transmitted and shared.

Complement with this superb interview with Glaser from How to Think Like a Great Graphic Designer and Glaser’s own 2008 classic, Drawing Is Thinking.