Stefan Sagmeister By Hand

By Hand is a new feature on Question Market. It’s something I’ve been doing privately for years. Writing a letter with some specific questions about creativity to someone I admire and hoping they write me back.

There’s an incredible site called Letters of Note that explores hand written correspondences throughout history. That’s what inspired me to start this. I love the layer of context that’s added by getting something in writing. You can tell if the person was in a hurry, or took their time enough to add drawings, or extra notes, or anything else. Maybe the envelope gets beaten up along the way. It’s added character. There’s intimacy to it.


If you’re a designer, there’s not much new I can tell you about Stefan Sagmeister. He’s towards the top of our food chain in terms of success, knowledge, and talent and I assume you know that already.

For anyone else that stumbles across this…Stefan’s body of work as a designer is heady and pure. He runs the studio Sagmeister & Walsh with his partner Jessica Walsh and has landed some of the biggest gigs you can aspire to have as a designer. Album covers for the Rolling Stones, Lou Reed, Jay-Z, and others. Work for Levi’s, BMW, and the New York Times. He’s exhibited and discussed his work all over the world.

He’s fascinating and someone I think all creative people can look up to. In addition to his success as a designer, he’s also one of the deepest, most sincere, and intellectual creatives working. He’s active in the design community and always trying to put more meaning in to what we do as designers and humans.

When I was first learning and practicing graphic design, there were designers and artists that I admired, and imitated. But when I saw Stefan’s work…things like this, and this, and this…I realized design’s ability to be thought provoking and expressive.

I know this seems obvious, but how creative design can be. His work unlocked that for me. I was learning the basics…grids, letter forms, color theory. Laying out things like letterheads, stationary, websites, advertisements…in pretty standard formats. When I saw his work, my design brain took the next position on the evolutionary chart towards being upright. I’m still working on it…

In 2010, I wrote Stefan a short letter and asked him:

  1. What is something all creative people have in common?
  2. What was one creative habit you had as a child?
  3. What is one creative habit you have now?

He generously wrote back the following… (transcript below as well)


His insight is wonderful and I can’t read these answers without his voice in my head. And, I love that he plans for certain tasks to be completed in the morning. I have a feeling that is something that’ll be explored again here.


Hey Derek,

Here are some quick answers:

  1. A desire for the new. A certain amount of fearlessness & guts
  2. I don’t remember being particularly creative as a child
  3. a) Work on many projects simultaniously. Switch to another one when I get stuck.
    b) Start with the difficult parts first thing in the morning.

Good luck and many greetings,
Stefan Sagmeister

Thank you for reading, and thanks to Stefan for allowing me publish this.


I Definitely Look Like This

How important is style in what you do?

What the hell do you think Houdini saw when he stared at a straight jacket? For a lot of creative people, perfecting a style is the achievement…the goal. It’s what enables a career to unfold. Once you establish a creative identity (style), the more articulately you can express yourself, or interpret the world.

In context of my own experience, I see a designer’s job as one that transforms gig to gig. The look should be determined by the message you need to communicate. I think not being tied to a style is part of the fun of my job. I understand that for some, it’s exactly the opposite. And for others it’s even a dirty word. That’s why I think it’s such an interesting topic. Is having (or not having) a style a necessity, or result of what we do as creative people?

What I am sure of, is that working within a style can be one of two things…incredibly limiting, or profoundly freeing. With that in mind, I asked Jay Shaw, Tom Papa, and Keith Buckley about how important style is in what each of them do.

JAY SHAW, Designer

Jay’s work is incredible. His ability and aesthetic evolution seem to be in constant motion. As creative director for Mondo (the Alamo Drafthouse’s equivalent of an art department), he’s contributed to some of the most successful major studio and independent film releases (and re-releases) in recent years.

Jay is a pure, true designer. I think he has an interesting relationship with design history (key art specifically). His knowledge of design history is apparent in his work, but each new piece of work he does also takes a firm, deliberate step forward.

Admiration aside, Jay has been friendly to me whenever I’ve reached out, so he generously gave me a little closer look behind his curtain.

How important is style in what you do?

“I think if I were a more competent illustrator having a “style” would be important to me. As it stands I really don’t. I go through phases where one approach appeals to me but I tend to stay pretty versatile aesthetically. If I have any consistency in my work it would be that things tend to look like they were created 40 years ago. I’ve got such an affection for commercial art of the 60s and 70s I can’t help but ape the popular methods of the time. The only drawback to moulding your look to the needs of the project are that it gives you (and the client) a little too much wiggle room sometimes. I envy artists who commit to stylistic parameters.

TOM PAPA, Comedian

Tom Papa is a classic. He’s a wonderful blend of new and old schools matched with an interesting depth. I think he makes interesting choices creatively. He’s got a relatively polished, clean style, but then he’ll have Rob Zombie direct his special, and dress the set like a game show from the 50’s. I love shit like that.

I worked on a tour poster for Tom a few years ago. As inspiration for the poster he explained to me that in the set (which became his “Freaked Out” special) he discusses fears such as aliens, our families, old age, and the possibility that there is no God. That description was as good as I could have asked for. It’s silly and profound, just as he is.

It could entirely be because I enjoy a drink in the same way he seems to in his bit about fitting in…but I get such a sense of comfort in my own skin after listening to him.

How important is style in what you do?

“It would be impossible to say that style isn’t a big part of being a comedian. However; I see style as almost a byproduct of what we do. Comedians often talk about their ‘voice’. Which is uncovering or discovering their true self that they bring to the stage and convey through the jokes they tell. Naturally when this happens you could say the comedian has a certain style.

Of course, one could manufacture a style without having anything to say but that is closer to a clown. Not that I’m knocking clowns. A guy who walks around with a red nose and worn floppy shoes certainly has style. But you may not want to hear his ‘voice’.

KEITH BUCKLEY, Musician and Writer

Keith and I share the home town of Buffalo, NY. I assume it’s lost on most people how accurately the band he sings for (Every Time I Die) embodies Buffalo, NY. It’s a personal connection for me. They’ve successfully interpreted the attitude, tone, energy, and spirit of the city in to their music.

I’ve always admired his range creatively. On a dime it seems he can go from smart to funny to loud, quiet, aggressive, or weird. I move slower than that.

He’s a fascinating combination of intellect and instinct. Perhaps style is the result of those two things meeting… With that…

How important is style in what you do?

“”Style” is the signature you put on performance. our music can’t hang on a wall like other art forms, so our style -the way we do it- is how we let the world know who it was done by.”

A straight jacket…something literally restricting, and yet completely liberating creatively…

More info on Jay at
More info on Tom at
More info on Keith at

Thanks for reading Question Market 3,


To Stay Sharp

What is the most recent skill you’ve developed?

I’m trying to figure out if creative development is something I need to stay focused on, or if it’s something that’s inevitable. I suspect that if I keep designing…if I keep creating things, it’ll be inevitable that I learn new skills in one way or another.

By committing to my work, I’ll either be adding more of myself in to the work, or developing new design-specific skills like figuring out a better way it retouch hair, or use geometry to help tell a story. Perhaps those are two ever-evolving avenues of creativity; how articulate you can be personally and professionally.

If you’re committed, I really think those two things are impossible not to evolve.

With that in mind, I asked Eddie Pepitone, Michelle Poler, and Dustin Stanton about what skill each of them have developed most recently.



I’ve worked with Eddie on a few things, and he’s always been incredible. He’s responsive, friendly, courteous, etc…everything you could want from someone you’re doing business with. More impressive than those great things though is his creative energy. He’s a stand-up, and as an actor, he’s appeared in some of the best comedies of the past two decades.

His stage sets are like an intense massage. There’s pain in it, aggression…but you leave feeling lighter, relieved, and seeing things brighter. He’s calculated, in control, and completely reckless at the same time. That contrast is incredible. This set is from a while ago, but is so interesting. He flexes every muscle a comedian has. Watch how far away he holds the mic at certain points, while still being completely effective.

I hear he’s even dabbling in politics and community organizing. I love that someone as versatile as Eddie continues to develop, but he does…

What is the most recent skill you’ve developed?

“I think the things I learn how to do are ongoing. Modulating my voice from the rage to soft-spoken guy is something I’ve been working on as I realize it’s very funny to go to extremes vocally with an audience. I have been more conscious of varying my tone and range and it’s all about just being more present and not panicking as a performer.

I used to think I had to get a laugh every second and I’ve finally realized that the silences or the spaces in between are just as important as the jokes. In fact it sets up the jokes!”


Michelle created 100 Days Without Fear. She’s Venezuelan and after studying at SVA in New York, she worked as a designer and art director. Then, through the process of conquering a list of fears she began telling her own story in a way that connected with others.

Her curiosity is what impresses me most. She’s been able to translate an exploration of herself in to exploring and influencing people across the world. She’s an interesting example of that intersection of personal and technical skill. I’m so happy that she said she’d answer my question…

What is the most recent skill you’ve developed?

“I believe that as artists we are constantly developing and polishing the skills we already have trying to become every day the best version of ourselves. 5 years ago when I got married I decided to buy a GoPro to capture in video my honeymoon adventure. We were going to Hawaii so I wanted to put together a short video to share with family and friends and also to keep for ourselves. My little brother was in film school at the time and he kindly edited a nice little video about our wedding day. I quickly learned the things you need to put into a video to make it entertaining, creativity was the main component. Two weeks after we came back from our honeymoon I gave editing a shot. People started to go crazy about the cool video I made and started to ask me to edit videos for them about their personal experiences. Shortly after, I became the official video person of the family and in my circle of friends. I created videos about meaningful occasions as gifts for the people I care about the most, but I never thought about doing something serious with my video making and editing skills. I would only do it for fun.

 Last year I decided to become a braver person by facing one fear a day for 100 days. I wanted to share my progress through social media so I decided to record myself facing the different fears, editing and uploading one video a day. After editing 100 videos consecutively I can see how much I’ve grown and how my skills have improved enormously. The thing I used to do for fun became my full time job. Most recently, I started developing video blogs (vlogs) which is different than shooting an adventure. So I had to learn all about cameras, lights, audio, tripods. Just when I thought I had everything under control, I had to start from scratch. So, yeah, we actually never stop developing and polishing the skills we already have. I wonder what kind of videos I will do next.”


Dustin is a graphic designer for the entertainment industry. He’s created lots of great key art, but his contributions to Paul Thomas Anderson’s films have always shook me up most. His interpretations of the stories are so nuanced and personal…exactly the thing those films need.

I worked with Dustin on a gig poster for Bill Burr. The poster was for a tour of California and Bill gave us the idea to interpret the drought that California was in. Dustin built a great narrative based on that concept which I followed through on.

What I learned from working on that project is that a designer should be able to think their way out of any problem. You’re given a creative problem, you figure out an answer to it, and then execute it. Having a purposeful answer is an underestimated tool. That seems obvious, but more often than I’d like to admit, I find myself trying to figure it out as I go. My point is that Dustin sharpened my creative problem solving skills. So, I’m curious what he’s been working on for himself…

What is the most recent skill you’ve developed?

“One of the recent skills I’ve been developing is self editing.

I once heard (or read) a quote somewhere: “He with fifty ideas has none”. I get it. I think I’ve been trying to work that philosophy into my work and provide my clients with more quality and less quantity – putting forward the ideas that I believe in and have good reasons to present to them. So far, it’s been working well with the people I work with.”

I’m glad that our relationships with creativity seem to keep evolving. It feels like there’s security in that. Something of comfort that can constantly shift from being personally rewarding, to professionally.

More info on Eddie at
More info on Michelle at
More info on Dustin at
Illustration by Brett Mikoll,

Thanks for reading Question Market 2,


The Question Market is Coming Soon

The Question Market will soon be bringing you insight to brilliant people’s relationships with creativity. How they approach creativity and the struggles and successes they have working in their particular genre of it.

Designers, artists, musicians, moms, chefs, athletes, teachers, barbers, butchers, boozers and more. We have more in common than you think.

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