Ann Willoughby on Her Life-Changing Mentorship with Milton Glaser

For Centennial Voices, part of AIGA's Centennial celebration of the past, present and future of design, we've invited industry leaders to write short essays that spark conversations within the design community and beyond by sharing personal experiences, reflecting on design history, examining the practice today or imagining the role of designers in the years to come.

After a chance meeting with Milton Glaser grew into a mentorship that saved her career (and her life), Ann Willoughby of Willoughby Design pays it forward by being an advocate for emerging young designers.

“I just don’t think I can do this anymore,” I thought as I stared with bleary eyes at the unfinished illustration on my board. It was 2 a.m. on a steamy July morning in 1973. After years of working late into the night as a freelance designer and illustrator and caring for my two (wonderful) young children by day, alone after a divorce (not of my choosing), I was at the point of utter surrender.

Still, I beat myself up: Where was my insatiable hunger to design? My passionate drive to succeed? I’d watched many of my design peers step up and hit their stride professionally while I’d stepped straight into a pile of diapers.

“Maybe things really are different when you have children,” I thought. I wanted so much to create a healthy and happy home for the three of us. But something had to change. Thus began my quest for a senior level design position at a studio or agency.

Serendipitously, I met Milton Glaser after hearing him speak at an event I attended, and he invited me to call him if I needed his career advice. Over the following weeks, we spoke often about how the design field was losing many talented female designers who were also mothers with children because no one was willing to change the status quo.

To this day I can still recall in vivid detail countless interviews with studios and agencies of every ilk—those run by classic Mad Men, the inarguably impeccable and everything in between.

In interviews, I was encouraged by the genuine oohs and aahs of executives as they pored over my portfolio. Yet no one was willing to hire a young mother with two toddlers who couldn’t work late at the office or travel at a moment’s notice. Nobody wanted to take a chance.

After a couple months of concerted effort and one fruitless interview after another, the thought “I just don’t think I can do this anymore,” started making regular appearances again. One gloomy day, I was at work in my home office when the phone rang. It was Milton.

“I was just thinking about your job hunt. How is it going?” he asked.

“Not so good. In fact, I’m not sure what options are left,” I answered with a big sigh.

What Milton did next changed everything.

“Well Annie, I believe in you and I know you’re going to find a way to reinvent your life. Please don’t give up on your design career,” he said.

World-class designer Milton Glaser, someone I admired more than anyone in the world, believed in me. He knew I was going to find a way to reinvent my life, and suddenly, I knew it, too. His words, spoken as fact, renewed my confidence and renewed my desire to think about my life and my career in a new way. It was the beginning of a mentorship and friendship that has lasted over 40 years.

Shortly thereafter, I rented a small studio. The name on the door read Willoughby & Associates. The rest, as they say, is history.

When you have confidence, the possibilities are endless. When you’re low on confidence, someone you look up to and who truly believes in you has the power to replenish it with just a few words. The only way you can pay this person back is to find and mentor people you really believe in, see for them what they cannot see themselves, and restore their confidence so they can go on to achieve their own possibilities. And so it goes.

(Thank you Milton Glaser, for this and countless other votes of confidence over the years that have led me to a lifetime of endless and fantastic possibilities.)