My Kinda Sad Portfolio Story

This week and next, we’re asking the judges of the Print Portfolio Review to tell us about their portfolios—specifically their first portfolios, and how they helped or hindered their early careers. Yesterday, Mirko Ilić told us about the “big paper salad” he brought to New York City in 1986. Today, Debbie Millman writes about her first portfolio.

The only job I wanted after graduating from college was to work for Vanity Fair magazine. Back then (the early 1980s), the magazine was a heady literary publication edited by Leo Lerman. The covers featured quirky designs by David Hockney and Irving Penn photographs of Susan Sontag, Italo Calvino, and Woody Allen (as Groucho Marx). I obsessively pored over each issue trying to crack the code of brilliance I was convinced they contained. Per the policy at Condé Nast, I dutifully dropped off my faux-leather, sienna-brown portfolio for review. My precious portfolio was filled with plastic-covered pages I’d edited and designed (and spent months agonizing over) for my school newspaper, The Albany Student Press, as well as overwrought logos for a pretend restaurant I’d named Cherries & Walnuts. It also contained several mock Vanity Fair covers I’d taken it upon myself to create; they featured a series of black-and-white Russian Constructivist–style wood etchings without any cover lines whatsoever. Miraculously, when I returned to pick up the portfolio, I was informed that Charles Churchward, the design director at Vanity Fair at the time, requested I come in for an interview. Human Resources would be the next stop.

One of the spreads in my first portfolio

This, to me, was the equivalent of winning the lottery. I spent every waking hour prior to the interview reorganizing the contents of my portfolio and trying on everything in my “career closet,” posing in outfit after outfit in an effort to ensure I could make the best possible impression. My wardrobe consisted of clothes my mother had lovingly handmade as a graduation gift. The morning of the interview, I settled on a royal-blue bolero jacket, a matching knee-length A-line skirt, a beige faux-silk (polyester) blouse with blue pin dots and an oversized, floppy bow in front, sheer black stockings, and flat black patent-leather loafers. I anxiously gazed at myself in the mirror and took a deep breath before leaving my mother’s Queens apartment. I knew that what happened next could change my life, and as I sat on the cramped, balmy express bus into Manhattan, I fantasized about befriending the Human Resources director, being invited up to meet Mr. Churchward, getting hired as his trusty assistant, working late nights and weekends, cavorting with the glamorous editors and art directors and designers, and, of course, spending my entire career being fabulously successful at the best magazine company in the whole wide world.

My resume at the time

I exited the bus on 42nd Street and Madison Avenue and skipped toward the Condé Nast building, my big bow billowing in the July breeze, my overstuffed portfolio banging against my legs, when the unthinkable happened: I tripped. I fell knee-first into the sidewalk. I toppled so hard and so fast that my portfolio went flying and three passersby came to my side. As they asked me if I was OK, I felt my stinging knee and knew without looking: I had an ugly bruise on my leg and a vicious tear up my stockings.

I didn’t have time to buy new hose, but I quickly realized that my skirt and the tactical placement of my now scuffed portfolio could mask the bruise. I lumbered on and made it to my appointment on time. When I met the Human Resources executive, I was mesmerized. She was unlike any other woman I had ever encountered. She was breezy and elegant and alluring in her a pale yellow sleeveless shift and a big jangly bracelet. She had the thinnest arms I had ever seen and the biggest office I had ever been in. She invited me to sit down and I shyly complied; I felt the hole in my stockings widen and prayed she didn’t hear the ripping sound. She looked through my bruised portfolio without uttering a syllable. I remember that I could hear the slapping of the plastic pages as she quickly rifled through them. When she finished, she shut it with a thick thud. She looked me up and down. And then we had the following conversation:


“So. What kind of design do you want to do?”


“Excuse me?”


“What kind of design do you want to do?”


“Kind of design?”



Me (with a furrowed brow):

“Hmm. Um. I think I would like to do any kind of design.”

She (with very furrowed brow):

“You can’t do any kind of design. You have to pick.”




“Yes. You have to pick. You have to pick editorial design or promotional design or advertising or custom publishing. You must choose one.”

Me (thinking to myself):

Well, I really want to say editorial but maybe I am not good enough, and though I don’t know what custom publishing or promotional design are, I will say “promotional.” But really, I would happily sweep the floors if they want me to.

Me (actually speaking):

“Um. Promotional?”

And then I couldn’t help myself. I continued talking:

“But I would do anything. Anything you need.”

And then there was silence.


“Well. Yes, then. I see.”

And with that, she sighed and made one sweeping gesture for me to take my portfolio back. I looked at her and picked it up. Though she said she would be in touch, at that moment I knew I was never going to hear from her again, and I never did. I made some small talk as I was escorted out; I remember asking her how long she had been at Condé Nast and I remember her replying “12 years” with a clip in her voice.

Several months later I got up my nerve and called her, but the person who answered the phone told me she no longer worked there. By then I had gotten my first job, as a traffic girl at a fledgling cable-television magazine. I worked late nights and weekends and cavorted with the editors and art directors and designers and, of course, I didn’t spend the rest of my career there. But when I worked there, I joyfully learned about editorial design and promotional design and advertising and even custom publishing. I realized how much I did know and how much I didn’t know and embarked upon what has become a lifelong journey in learning about the abundant and bewitching specialties in the marvelous discipline that is considered graphic design. And I look back on that first portfolio, now long gone, with a combination of sentimental nostalgia and a little bit of shame. But all these years later, I’m still proud of those Russian Constructivist copy-free covers.


Early fragments of this essay appear in the book Essential Principles of Graphic Design by Debbie Millman (HOW Books, 2008).

12 thoughts on “My Kinda Sad Portfolio Story

  1. Sulabha

    This is so true, even I had such an interview. There are so many things we don’t know when we join fresh! I wish to grow like you. Design is such a subject where I think everyday you learn so much. And yet it is not 100%.

  2. edr3

    Man, this sure brings back an embarrassing memory. I remember wanting to work for the biggest, hottest agency in our area. One day, out of the blue, I picked up the phone and called the head of account services. I met her at a clothing store where I worked part-time, she bought several pieces of clothing I designed for the store. We set up an “informational” interview.

    When we met she was wearing one of my suits, seeing her in one of my suits made me feel so great. I showed her my graphic design school portfolio and she mentioned she could introduce me to “The” Creative Director. I could immediately feel my nerves starting to fire up and the butterflies beginning to swarm inside my stomach. I was really young. I had heard so much about this Creative Director at school. Seems like everyone in design school at that time had tried unsuccessfully to meet with him. We all thought he was a deity or something.

    I entered his office shaking with nerves. I felt absolutely nauseous, unworthy and sweaty when I shook his perfectly manicured hand. He was the kind of man I wanted to be—well-dressed, talented and just plain old cool. When he spoke he sounded rich, smart and otherworldly. All I could think about was if I opened my mouth I’d throw up all over his beautifully furnished office. When I left I threw up in a trashcan outside their building. I walked to the bus stop in shame, caught the bus back home, climbed into bed and pulled the covers over my head.

    I never had the guts to return to that agency. What I learned from that experience was to always be prepared when opportunity knocks.

  3. Tom Foerstel

    My first interview: Entering the very tall builidng on Wilshire Boulevard, my ENORMOUS black portfolio case caught the wind and bumped an extremely well-dressed AE type next to me. His reaction, to the delight of everyone within earshot: “Is there a ping-pong tournament today?” I was crushed!

  4. Robin Andrews

    Classic story, I can relate. One of my first interviews was with a recrutier who had a white long haired dog in her office, the dog’s fur got all over my many plastic sheet covers, a nightmare to remove. Thanks for sharing.

  5. Tina

    I worked at Conde Nast for many years and at certain points interviewed within the company for what I thought might be a better spot. Interviewing at Vogue with then Art Director Roger Schoening- I unzipped my enormous portfolio only to have a cockroach walk out from behind a page. Roger took notice and in a feeble attempt to save myself said “That’s my Rep!”

  6. Joe

    At my first interview, ever, I stopped in a McDonalds to use the bathroom. While washing my hands, I pulled the lever on the liquid soap despenser (a flawed design which had the user pulling *toward* them from the wall – now no longer made). Since it had not been attached to the wall correctly, as I pulled it for a squirt of soap, the entire quart container, missing a top (this was pre plastic bag insterts and soap smelled like motor oil) flew off the wall directly at me onto my shirt and tie. I dashed out (no paper towels, of course) and ran to the order counter. I yelled “YOUR STUPID SOAP FELL OFF THE WALL ONTO ME! I NEED A TOWEL!” The shocked teens did not get it at first but, one guy, at the fries salting station, tossed me an oil soaked towel. Ugh. It was all I had. I was able to keep my suit buttoned at the interview and cover the giant soap and French fry oil smelling stain on the bottom of my tie and shirt. Luckily, I had taken the jacket off and put the portfolio away from the sink.Later, I got a much better job at a different studio. It actually turned out to be the best job I have ever had so, I guess, it helps to have a bad interview before the one you should have at the place you should work.

  7. Chuck

    We hand over our heart and soul to a stranger, dream of our ideal career, Deep down hoping and praying that our protfolio will really open the door for us. Memories, such memories. Now when I see portfolios, I crave for seeing somw really cool work, listen to the back stories and see that they are in the same place we all once stood. Give the advice you wish was given to you, nuture and mentor and hoe for the best.
    I lways look in their eyes – that’s where the real truth lies and tells if they have what it takes.
    By the way, I especially enjoy the use of Peignot in the protfolio and the resume. We use to cal it the “Mary Tyler Moore” font.

  8. Monna

    LOL, oh do I have some of the same stories! Tripping, dropping, not knowing how to answer “the question” and yes, all the things you thought you would do at your dream job, you have actually done.  I say that as I look around my office at; the billboard shots, the transit cards, the invitations, the posters, and postcards, etc, and the awards that I have received make it a little more special. (note: the Clio, it’s actually a photo of one I keep up for inspiration!) LOL