Master designer Milton Glaser and a lifetime of evolving his work.

No sooner had I received an update on my order for Mag Men—the story of Walter Bernard and Milton Glaser’s design work on over 100 magazines—Within minutes, I got a news alert on Milton’s passing. He was 91, and I believe he continued to design up until his last day. In a 2018 interview, Milton said about work, “If I woke up in the morning and didn’t have a place to go, I’d go nuts. It’s a great reason to keep on living. Retirement is a trap.

Milton is and will forever be known as the creator of the “I [heart] NY” logo created for a 1970’s tourism campaign to draw visitors to the city. Not satisfied with merely typesetting the phrase, he turned it into an icon, sketching the first draft in the back of a cab with a red pencil on the back of an envelope. He is equally known for a promotional poster of Bob Dylan, which was included as a gift in Dylan’s 1967 greatest hits album. These are just two projects of an enormous catalog of work that also includes the creation and design of New York Magazine and redesigns of TIME, The Nation, Esquire, and The New York Review of Books magazines to name just a few more.

From my perspective, he led a very fulfilling career, and I think that had a lot to do with his non-stop curiosity, willingness, and capacity to learn.

Years ago, I had the privilege to see Milton give a lecture on design. It was in 2011, and I had recently volunteered to start the San Francisco chapter of Creative Mornings. Up until that time, there were only three: New York City, Zurich, and Los Angeles. Because it was still so new, I had yet to attend a Creative Mornings event. So as part of my onboarding, Tina (the founder) and I looked over the calendar for the next best session to attend and observe how the event worked (yes, they shot video of the speaker, but not the entire event, and I wanted to see all of the details). As it happened, the next Creative Mornings NY featured Milton Glaser at the SVA Theatre.

There were two moments during Milton’s January 2011 appearance that have always stood out for me, and that I will never forget. The first was his preamble into his talk. The second is how he dealt with failure on stage during his presentation.

Milton came to Creative Mornings intending to talk about a series of hidden relationships between all the things he had been working on in the last five years. A look into the nature of continuity and change in our work as designers and professionals.

He began with a story of two Italian men and what we can learn from how they approached life and work but arrived at similar outcomes as artists. It’s so good that I transcribed the entire story:

“In my mind, I have two artistic heroes. One is Picasso and the other is Giorgio Morandi who I studied with in the ’50s in Italy. And the interesting thing about them is they represent these extraordinary polarities. Picasso was a man who wanted everything—Wanted all the fame, all the money, all the women. That was Picasso. Morandi, on the other hand, was a man that wanted nothing. He just wanted to teach a little, once a week, in a very ordinary school in Bologna, and then go home and paint.

Even in the work of these two what seems to be contradictory figures or polar opposites figures, what you discover if you pay attention is the extraordinary range of development in every case.

In Picasso it is very easy because of his willingness to abandon what he already succeeded at is one of the sort of extraordinary things about him. Picasso would start doing something and become brilliant at doing it and then forget about it and then move on to something else. He was willing to succeed and then abandon his success.

And I always believed that one of the great difficulties in professional life is that you can’t fail enough without being out of the profession. In professional life, you have to succeed and go from one success to another in order to become visible and important. In artistic life, you have to fail over and over again in order to understand what you are doing. In our particular profession [design] failure is not acceptable and you might say as a consequence of that there really isn’t enough development because you don’t go beyond your sort of self-description of what it is you do and how you do it.

But in the case of Picasso, his courageous abandonment of his own accomplishment in history is one of the reasons he was able to move through the issue of style and manner into something else that by failing he learned.

There was a show of Morandi a couple years ago at the Metropolitan [Museum of Art}, where you really saw all of these pictures—painting and etchings—that look almost identical and then you discover that everyone is different. That in a certain way the development and change is as profound as Picasso except it is done in such a way that is virtually invisible. But I you walk through those galleries—as I did at the time and even though I know Morandi’s work you were overwhelmed by the different manifestations of the singular ideas about light and form.

In any case, what I urge you to do is to fail more often in your professional life if you want to find out what it is you are capable of learning.”

As far as I was concerned, Milton could have stopped at that moment, and it would still be the best Creative Mornings ever. Looking around at the audience, I could tell they, like me, needed some time to let that story sink in, but the teacher continued.

Milton launched into the first few frames of his presentation when it became clear something was wrong. He paused and muttered to himself, looking unsure about what he saw on the computer, but he pushed on. He continued to speak to the work represented on the slides until around twenty-four minutes. He looked to the crowd, stopped the presentation, and apologized to the crowd: “I’m sorry this really is a separate presentation that has found its way onto of this morning’s presentation. And it doesn’t really belong here. Quite unrelated to our thesis this morning.”

Cool as a cucumber. Most speakers I know would have caved if they didn’t have the right slides and would have ended their presentation right then and there. Not Milton, he powered through what he had (often skipping slides) to provide a compelling narration of his work while keeping to the theme of the intended lesson.

On that morning, I learned that there is more to compelling presentations than flipping through hundreds of slides and well-timed animated GIFs with every word memorized and rehearsed like a K-POP performance. As accomplished as he is, Milton could have paraded his top hits and regaled us with a flashy presentation with behind-the-scenes stories and quotes of famous people responding to his work. Instead, he invited us into a more vulnerable place filled with curiosity: questions and wonder. And he did so in a masterful way to inspire us to make his point about finding new ways of evolving our work (and who we are) whether to stop and start over again or spend years on subtle, incremental changes.

Looking back on his work Milton successfully made a case that his career is a successful contemporary blend of Piccaso’s constant reinvention and Morandi’s persistent method. In the middle of his lecture, Milton dropped this line: “Color is one of those subjects you never can fully learn it’s the most mysterious manifestations of the arts.” Wow! If that’s how he felt about his command of a core of art and design, then it is easy to see how he kept going into the studio each day—what an incredible inspiration he was and what an inspiration his work will be to future generations.

I’m thankful I got to be a witness to the greatness of Milton Glaser (albeit briefly) and for the lessons I took away from that day. And the many lessons I still have yet to learn.