When I was in college studying music I wanted to take a design course, which was a problem, because Wesleyan did not have a design department. There was an art department, and buried inside it, a single typography course that required an interview.
I showed up confidently to the interview with design work I'd done on my own: posters and album covers for a band I was in, some web designs printed out on loose paper and stuffed into a folder. The professor looked it all over and instead of addressing the work, asked if I knew what typeface the New York Times used. I was startled and admitted that I did not. There were students trying to get into his class who did, he replied, and he only had a limited number of spots.
For years I remembered that rejection, feeling somewhat baffled and somewhat offended. How was I supposed to know that specific typographical fact before taking the class? Wasn't the point of the class to learn about typography? I really wanted to learn but didn't know where to start.
It took me a long time to see the question for what it likely was. He was selecting for students, studio art majors mostly, who already had more foundational context on design, and more developed visual sensibilities. It was his class after all. He didn't need to critique my beginner's portfolio honestly, or to tell me to stick to the music program, so he hit me with typographic trivia.
After college, I went on to study in an MFA program at Parsons where I learned more about design and typography. In my twenties I worked my way up the ranks as a designer at agencies and then as creative director, leading teams of designers, for two news organizations in New York. Today I run a design and creative studio and still think of most challenges from the perspective of a designer.
I now look back on that failed undergrad interview, not with shame, but with compassion for the eager budding designer who didn't know what he didn't know and for the teacher, who rejected me with a question I couldn't answer. There's an art to giving feedback, of tailoring it to balance the truth as you see it, what the recipient can hear, and what the situation requires. An honest critique of those early designs would have crushed me. What felt like arbitrary gatekeeping at the time was a kindness.