The legendary Gail Anderson agreed to judge, host a panel, and be interviewed (she clearly needs to work on establishing boundaries). We are deeply grateful for her generosity and wisdom.

We sent out a questionnaire to some of our judges and past Ascenders as a light-hearted Proustian exercise. This interview was lightly edited for clarity.

What was your very first job?

Nurse’s aide, Kingsbridge Heights Nursing Home, Bronx, NY. Really.

First design job?

Assistant Designer, Vintage Books (Random House).

Did you go to school for design? If so, where and what was your major/concentration?

School of Visual Arts in NYC—the major was called Media Arts at the time.

What was your earliest design class?

Cardinal Spellman High School—Studio Art, with Ms. Francis.

Name one of your favorite projects from early in your career.

A call for entries for American Illustration using a Jonathan Hoefler typeface that he could not understand people liking so much.

Are you embarrassed by your old work?

I hate looking back. I’m even cringing at the question itself.

What advice would you give to your younger self?

Lighten up. Travel more. Up your 401K contribution.

If you could change one thing about your career trajectory, what would you change?

It might have been fun to have gone to grad school at some point.

What is a barrier to entry facing today’s designers that you might not have?

You have to be a Swiss Army Knife of technical skills. Yikes.

What is something that today’s young designers have that you wish you had?

They are Swiss Army Knives of technical skills. Yikes.

Are there any up-and-coming young designers you admire? Young being under 35 and/or younger than you.

Two recent grads from SVA, Mo Hinojosa and Shantanu Sharma. Love them both.

What top 3 traits are you looking for when looking at young designers’ work?

Good type skills, the ability to communicate well, and a little bit-o-wit.

What are 3 things that you hate seeing in young designers’ work?

Spelling/grammar errors (too much Catholic school for me), stretched type, too much trendy design.

Name one way in which you continue your education.

Working on design and typography books with the esteemed Steve Heller.

If you could change careers, what would you do?

Writer. Or if I’d had the brains and a science-head, a doctor.

What is your favorite job you’ve ever had?

I was young and wide-eyed at the Boston Globe and had good friends, a big apartment, a lovely roommate, and my first new car. And I was learning something new every single day.

What is the worst job you’ve ever had?

One job reminded me that I’ll never be allowed to sit at the cool kids’ table.

What is a job you’ve had that would surprise people?

OMG, the nursing home job. I actually wrapped dead bodies more than once.

Which of your peers do you most admire?

My sister, Gerry.

What do you wish you were better at?

Even simple math still challenges me.

What in your career are you really good at?

I think I’m a pretty decent writer. And I can perform type tricks.

How do you define a successful career?

Still being excited by what you do many years into it is the definition of success.

What tools do you need to have a successful career?

Resilience, stamina, dedication, and the ability to take chances and learn from your mistakes.

What food must be accessible to you in order to work well?

Minute Maid Zero lemonade or fruit punch. And ice. Lots of ice.

Who do you credit most for your career rise?

Fred Woodward and Paula Scher.

Who do you consider your teachers?

Carin Goldberg, Richard Wilde, and Lynn Staley.

If you could collaborate with anyone (that you haven’t worked with yet) who would it be?

I would like Carin Goldberg to teach me how to embroider.

Any books, films, or albums that have defined or changed the way you think?

Learning about jazz while at Rolling Stone made me smarter.

What hobbies keep your sanity intact?

Apparently, my hobby is psychoanalysis.

Do the above inspire your career/practice, or do you compartmentalize to get away from it?

At this point, I’m happy to stare at the top of Overlook Mountain in Woodstock. Or watch another episode of Grace and Frankie. They give me hope that I may finally get to sit at the cool kids’ table in my 80s.

How much sleep do you get?

About six hours on a good night, never more than seven. Left to my own devices, I’d be asleep right now.

How necessary do you find “routine”?

I need structure, and something as simple as taking my trash to the town dump on a Saturday morning checks that box for me.

Would you like to retire?

I’ll be 60 in a matter of minutes, but I just started a new chapter and I need to see how the story turns out.

Anything that worries or frustrates you, looking at the future of design?

Mock-ups, $5 logo sites, the metaverse, and designers stretching type.

What excites you about the future of design?

Seeing my SVA students so jazzed about being designers. That feels just great.