Schoolin’ Life: Anna Raff

In today’s edition of Schoolin’ Life, we chat with New York-based illustrator Anna Raff.

A photo posted by Anna Raff (@annaraff) on

When you were in your 20s…

What expectations did you have for yourself over the coming decade?

I expected to reach a certain level of success in my career as a graphic designer. But what that benchmark was, I’m not really sure, and I didn’t consciously set goals. What I most cared about was doing creative work that I found interesting and challenging, and making enough money to support my travel addiction which I’d honed during and right after college.

In what ways did society shape your expectations of yourself?

Because of my family background, my friends, and the creative industry in which I worked, I was surrounded by a group of very open-minded people, who weren’t necessarily adhering to any one set of norms or expectations. Even if they were, they weren’t forcing it upon others who didn’t fit in—this was New York City, after all. Also, I never pictured myself as a parent, so perhaps that eliminated a big element of societal expectations for a young woman like myself.

What was your first job like?

My first job out of college was designing corporate brochures and presentations at an architectural firm in London. I had travelled there with some friends, after enrolling in a work exchange program which got us to get 6-month work permits in the U.K. Before leaving home, I had sent out a few résumés, but this architectural firm was the only place listed in the program guide that was remotely related to my main interest at the time, graphic design. My résumé had this logo I designed in school at the top—I still have a copy of it somewhere. The logo is okay, but the rest of it is crap! Based on that, and their random needs at the moment, I got the job. Ironically, here I was, an American kid, so happy to be working in London, on Oxford Street, surrounded by all this fantastic, historic, architecture, but working for a firm that designed the most hideous, god-awful, American-style shopping malls. Also, this was all before desktop publishing, and despite taking a few design classes in college, my knowledge of manual typesetting was minimal, so I mostly got by on my wits and earnestness. Kindly, they offered to do the paperwork to extend my visa, but I knew I was done. The nice thing was, the job paid pretty well, and enabled me to do a significant amount of traveling afterward to perpetuate my postponement of looking for a “real job” back home.

What was your first apartment like?

The flat my friends and I rented in London was basic, but more spacious than my first New York apartment. We even found 400 pounds in an empty drawer when we moved it—that was a good day. We knew it most likely belonged to the previous tenants, but the jerky landlord would just pocket the money if we told him, so we used it against our rent. My first place in New York City—where I moved shortly after returning to the U.S.—was a small, railroad apartment in the West Village that would have been fine for one person. The landlord had put a thin wall down the middle of the bedroom to create two rooms, so my roommate and I could basically fit a twin bed into each, and not much else. Being the West Village, it was super noisy, especially on weekends. I remember motorcyclists tearing up the street several times into the early morning, setting off car alarms as they went. That was pleasant. Oh, and that was the first place I saw a water bug fly. Gross.

Did you experience any big life changes?

In my mid-20’s, I moved into another apartment by myself, which was incredibly liberating and empowering. Also, my best friend came out to me. I couldn’t believe that I hadn’t figured it out, but it made everything make so much more sense. It really affirmed that he was (and still is) my best friend. This was during the AIDS crisis, and I remember the first thing I said to him was, “Be careful!” Then I think I told him how proud I was of him…at least, I hope I did. I’m still very proud of him.

In what ways did your friendships change?

Certain friendships that seemed very important in high school and college fell away, while others only got stronger. I came to terms with all that; it was okay for friends and friendships to evolve, and not always toward the same destinations. It’s better to let go, if it’s not working anymore.

What did you learn through your romantic relationships?

That I was completely naïve.

How did your relationships with your family change?

I’ve always been quite close to my family, so I think the only difference was that I was relating to them more as an adult.

How do you feel society viewed you?

As a geeky-looking, somewhat athletic, artistic, straight girl who didn’t really like girly things, some people probably put me into a box of some sort.

How do you feel you changed emotionally?

I started to learn about what was really important, but to be honest, I made much more progress with that in my 30’s.

How did you change intellectually?

By the end of my 20’s, I’d learned the complete suite of Adobe products…oh, and Pagemaker and Quark. That’s probably not what you meant.

In what ways do you feel your identity changed?

Through work, travel, and play my confidence got a boost. I played softball for my publishing company’s team, and that was great fun. I hadn’t played at all since junior high, and I’d always been quite good, but somehow in my teens, felt it was too “butch” —a very ignorant assessment, I might add. Once I joined this work team, I realized how much I missed playing, and how I identified myself as athletic, and that that was okay. It was also great fun to get up to bat against these teams, where the men would see a woman at the plate, and come closer into the infield. Then I’d proceed to whack the ball over their heads.

How did your worldview change over the course of the decade?

Travel really made clear the isolation many Americans experience, having never stepped into another country and out of their comfort zone.

What was the most embarrassing moment?

Drinking too much, and barfing into two plastic mugs while on the Trans-Siberian Railroad. The most amazing thing is that the guy, who is still my best friend, carried the two cups through a moving train to the nearest toilet to dispose of them. In the middle of Siberia! And he’s still talking to me 28 years later. Now that’s friendship.

What was your biggest disappointment and how did that affect you later?

I had a few disappointments at work, like not getting a promotion as I thought I should have, but I chalk that up to not asserting myself enough. These moments also spurred me on to seek out the next thing, the next challenge. And at some point, I realized I really didn’t want to supervise others at work, so I had to seek out positions that allowed that. By my early 30’s, I’d landed a job as a one-person design department at The Metropolitan Museum of Art, where I worked for ten years, until I returned to school to pursue a career as an illustrator.

Who was your biggest influence and why?

Oh, definitely my parents. They’re just really lovely, interesting people who always made (and make) me feel like I can do no wrong…within limits, of course.

Is there any one experience that you feel defined the decade? Or one historical moment that changed you?

When I landed a job doing design at a children’s book publisher. I had found the industry where I belonged, and it’s where I work now, albeit as an illustrator.

Do you have any regrets? Are there things you wish you’d done, hadn’t done, or done differently?

Perhaps I could have drawn more in my 20’s. At some point, I stopped making handmade cards, and other projects that involved illustration. It took me almost a decade and a half to figure out that I really should be doing that as a career. But perhaps I needed the time, I don’t know.

Is there a story that you feel best sums up the decade?

I think that one about barfing in Siberia is a pretty good one.

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