No Surrender

What’s the closest you’ve come to giving up and doing something else?

Every pursuit of a creative profession is different. I learned I will not stop being a designer a couple years ago. I was more anxious about a poster project than I had been for any other I’d ever worked on. I feared my career was on the line.

Momentarily, peace of mind came with the realization that even if the project is dropped completely, it’s not going to erase my ability to, or interest in design. In my head to that point, my entire career was at stake with each gig…

That’s an insane way to work. Operating that way makes the work suffer. It’s a disservice to you, your clients or audience, and anyone you care about. Do not do that.

It’s a weird topic…giving up. It can be interpreted different ways. It can be smart. Realizing you’re not equipped for whatever it is you’re doing, and putting your time and energy elsewhere…could be brilliant. It can be looked down upon…seen as not having the strength to work toward and achieve a goal. And it can be a bunch of other shit too…likely filled with corporate buzz words I don’t really want to use. So with that, let’s get to the thoughts of some amazing creative people.

Below, I have Dick Zigun, Joanna Hausmann, and Midnight Marauder to describe brushes they’ve had with creative instability, how, and why they persisted…

Dick Zigun,
Founder of the Coney Island Circus Sideshow

Dick founded Coney Island USA in 1980 and since then, has dedicated his life to the unordinary. Coney Island is a magical place, and Dick has everything to do with it’s modern identity. Coney is among the main elements in the make up of New York City. At the same time, it kinda has nothing to do with New York, and can even feel like something far, far away. It’s got it’s own thing going.

Dick established, and maintains that identity. He’s a complete, true creative, and seems hell bent to show the world that it can be seen differently. That’s what I’m shooting for as a creative, too. I don’t know Dick, at all, but he was wonderful enough to tell me a bit about himself…

What’s the closest you’ve come to giving up and doing something else?

“In Fall of 1995 we lost the lease on the Boardwalk building that had been our headquarters for 11 years. Half our Board of Directors resigned & we obviously had no funds & no right to keep on. I made a personal choice to lease another building on Surf Avenue, the 100 year old NYC landmark we now own…but at the time colleagues thought I was insane & I questioned my sanity as well. I maxed out credit cards to buy building materials I couldn’t afford & took a F/T outside job to keep our staff going. I lived in a tiny room with 2 snakes 2 cats and a dog.

For years I lived in the sideshow building with no real life of my own but…EVERYTHING good that’s happened since that insane decision 21 years ago has been the direct result of the insane 1995 choice when I should have given up & gotten a job teaching college.

Joanna Hausmann,

In most instances, Joanna’s brain is likely to be in three places at the same time. Here, there, and everywhere. Her comedy and writing are manifestations of that. She’s studied, quick, and two steps ahead of you, albeit in a different direction…

I get the sense that she’s searching, creatively speaking. As a collaborator, that’s incredible to work with; it’s ideal. In my case, she makes me a better designer. That was not an alliance I expected to gain when I met her, a comedian.

I got to work with Joanna every day at a website called Flama, which previously employed us both. She’s now a correspondent on Netflix’s Bill Nye Saves The World, and a regular performer with the Upright Citizen’s Brigade in New York. Here’s what she’s got to say…

What’s the closest you’ve come to giving up and doing something else?

“I think about giving up all the time. Every single time I have an audition I get so stressed I wonder what my life would be if I had a “normal” job with benefits and Keurig machine. Every time I have a big show I try to convince myself I don’t have what it takes to make people laugh. Every time I press send to an email that has a writing sample I spent days agonizing over attached to it, I think “this is stupid Joanna, you wasted your time.” I did the math. I have these sabotaging thoughts at least twice a month. And I used to take them seriously …. now I don’t.

The thought of quitting is never fueled by indifference; it is fueled by fear. The fear of failing. The fear of being judged. The fear of realizing my dreams are silly and unattainable. It’s seems easier to just quit and never find out what you fear the most; I’m not good enough. Once I realized the thought of quitting is actually a reflection of how much I cared, I knew I would never quit. The thoughts will come. And they will come religiously. But when they do, I know it’s a sign I’m doing something I fear which means I’m doing something right.

Midnight Marauder,

When I look at the film posters Midnight Marauder has made, I feel I’m spending a single moment with the film. His choice of image, what other image(s) it’s paired with, the colors, and type, all let me know what it’s like to live within that film.

He’s incredibly profound and articulate with the most basic ingredients…image, color, type, and composition. That’s it. His work is tonal, and atmospheric…it tells me very specifically what I’ll see, and so very little at the same time. That’s the perfect bait to get me to a movie. It’s simple, pretty, and enticing.

I’ve admired his work for a long time, and was thrilled to learn a bit about his background…

What’s the closest you’ve come to giving up and doing something else?

“That’s a pretty refreshing question. I don’t think I’ve ever been asked that before from anybody.

It’s definitely happened quite a few times, I’ve had some major set backs and failed a few times along the way. I don’t want to give up … I don’t want to give up on myself or my family. I’ve always wanted to work in film and I kinda fell into graphic design cause I failed in comic books and illustration. So this means everything to me. My passion is that strong and I won’t give up, ever !!

Whether it’s staring you in the face, or something you always notice at just a bit of a distance, that fear of everything going south always seems to be there. Ain’t that some shit.

You have to respond and adjust to the circumstances before you in order to survive. Change, and grow, yes…but give up, nah.

More info on Dick at
More info on Joanna at, or
More info on Midnight Marauder a
Header image by Derek Gabryszak.

Thanks for reading Question Market 8!


Professional Practicer

Do you practice for the work you do, and if so, how?

I very rarely practice, in the traditional sense of exercising specific skills. I do a lot of studying…looking at the work of other designers and other creative people’s work, but practice is rare. Round 1 presentations to clients are the closest thing to practice that I do. It’s where I’m experimenting and working out a bunch of ideas and executions that will likely be killed. Is that unprofessional? Irresponsible? Likely, I think.

My working style may be closer to an improvisation…in that the work I’m doing for my clients is exploratory. It could have a dozen different interpretations. I aim for that more than executing a style that I’ve practiced and perfected and then plug their information in to that.

What’s unfortunate is that I’m certain I’d be a better designer if I practiced more. And perhaps my work would be more original…less derivitive. Or more technically successful. Less studying, more practicing…

Practice is safe ground for failure. They’re kind of one in the same. Failure and therefor practice, could be among the most obvious steps to successful work. The benefit is undeniable.

To dig further in to this, I asked Adam Lowitt, Adam Maida, and Steven Feinartz to describe the role practice plays in their work…

Adam Lowitt,

Adam started working for The Daily Show as an intern in 2002 and has been there since. Not as an intern. He’s an executive producer, writer, and on-air correspondent. I think longevity is somewhat rare in creative jobs. So working with the same company for that long is certainly something I admire. In addition to what Adam contributes to the Daily show, he consistently performs stand up comedy as well.

Whether you enjoy The Daily Show or not, he goes to work every day for one of the most respected and prolific comedic and cultural platforms America has to offer. With that…

Do you practice for the work you do, and if so, how?

“Practice” in comedy is always an interesting concept because the term denotes that there’s a final product.  At least where I work, on The Daily Show, you could say the making of that day’s show is just practice for making tomorrow’s show.  I think “refining” is a better term, which is what we do all day, everyday.  Can this joke be funnier? Can this graphic be clearer? Can this take be stronger?  And once the episode airs, hopefully the staff doesn’t get too drunk after work, and we’re able to make an even better show the next day.

I treat my standup pretty much the same way.  Each set is practice for the next. The writing and rewriting of bits, figuring out how to perform a joke instead of simply saying it.  There are no comedy drills for that, it’s just logged hours onstage. That being said, I’ve often fantasized about some comedy version of Duke’s coach Mike Krzyzewski that i have to meet up with at six a.m. every morning to hone bits.  We’re both wearing tear away pants and he’s got a whistle that he blows every time I forget to enunciate the word “Jewish” in one of my punchlines.

Adam Maida,

Working out of Rochester, New York, Adam is one of the best designers in the western New York area. He’s created some incredible work for the New York Times, and Criterion Collection, as well as for other entertainment venues and social causes.

I’ve gotten to collaborate with Adam on a handful of projects. He’s always had great ideas to contribute, and executes them in phenomenal ways. He’s got a great sense for how to use collaged and illustrated elements. He uses them in different ways than the rest of us.

His work is so interesting to me, and I regularly revisit (or study) it. So, I was curious to know more about what goes in to it…

Do you practice for the work you do, and if so, how?

I find that simply experimenting with my own work, wether its for a client or just personal, is the best form of practice. Anything from simply combining two opposites in collage to animating something i’ve painted. I think the action of playing with our work is inherently the best kind of practice for any artist . It is one of the few methods one can partake in to simply find something internally or externally which ceased to exist beforehand. This I believe improves our abilities to not just draw or design better, but to think and communicate better through our work as well.

Steven Feinartz,

Steven is a director who is primarily in service to the comedy industry. I was introduced to him when I worked on posters for a documentary he directed about a stand up comedian (who I chatted with for QM2) named Eddie Pepitone.

In addition to that documentary, Steven has directed and produced comedy specials for Seeso, Netflix, Comedy Central, and Showtime. I know he keeps busy, so I was wondering how he stays sharp…

Do you practice for the work you do, and if so, how?

I do try to practice as much as I can, but practicing can mean a lot of things as a Director. I try to absorb what other work inspires me and at the same time try my best to develop my own voice. I’ve also taken to become a little more hands-on with the camera than I used to be. Exploring what different lenses and lighting techniques do to the image is so crucial to being able to express what you are looking for visually to your collaborators.

Most of what I’m working with is in the comedy space. Whether its documentaries, specials, shorts or music videos, I always need to think what best serves the subject or story. For specials in particular, I practice in becoming accustomed to the comics’ style or tone, and plan on shooting as true to that as possible. As a Director, you have to be available to so many people and at the same time you are the one making the final decisions. There is still nothing better than on-the-job training. For me, it’s how I’ve learned from my mistakes and apply that to what I’m doing that has made me stronger.

It seems that each of us have integrated practice in to the work itself in one way or another. I think that’s interesting. We probably all used to practice in a more traditional sense, and now we just do the work.

For professionals, it seems, practice is an ambiguous concept. I suspect Larry Bird would disagree.

More info on Adam Lowitt at
More info on Adam Maida at
More info on Steven at
Header image by Derek Gabryszak.

Thanks for reading Question Market 7!


My Ideas Are Great, I Think

What part of your creative process causes you the most stress or anxiety?

There’s a group of posters in the Museum of Modern Art by a graphic designer named James Victore. His work and general attitude are loud, and aggressive, and incredible. During a Q&A several years ago, I asked how stress affects his work. “Well shit, Doc…how much time do you have?” he said.

A lot of stress in creative jobs is self-generated. There’s very little right and wrong in what we do. A lot is left up to subjectivity. I’m right, you’re wrong…none of it matters really…you are right, I am wrong. And the other way around. It’s always this way.

That’s how I see stress in creativity. Constantly, I’m wondering and poring over the question…is this decision right?

Here’s a glimpse of that from a designer, comedian, and helicopter pilot.


Jessica is quite simply one of the best young designers America has to offer.

She’s created incredible work for some of the largest and most respected companies, people, and institutions there are to work for. So with that, I’m thrilled she’s as grounded as she is talented and gave this glimpse in to her creative process.

What part of your creative process causes you the most stress or anxiety?

“I’m probably the most stressed out right after I get off the first creative call with the client, before I have time to sit and think and scheme about what I want to do. Once I sit down to research and brain storm, I feel so much better about the project as a whole. Another time I generally feel stressed out is when pricing a job. It never gets easy for certain kinds of jobs.”

Helicopter Pilot/Photographer

Bruce drives a helicopter around while photographing things for a living. What an insane combination of disciplines. Please read the following, but absolutely look at his incredible video reel to properly understand what exactly he captures while high up in the sky.

I discovered Bruce several weeks ago because Twitter is amazing. He’s a photographer, television broadcaster, and helicopter pilot and works primarily in service of the entertainment and news industries.

His work is amazing and that’s why I’m fascinated with what his working relationship with stress and anxiety is…

What part of your creative process causes you the most stress or anxiety?

“The anxiety comes as we broadcast live reports from our airborne production studio and since our reports are “Live” we only get one chance to get it right. Coordinating our “Live Shots” with the TV station’s control room producer via two-way radio, coordinating helicopter shot location with the pilot, the pilot coordinating with the air traffic controller, thinking of what I’m going to say live on TV during our report, cueing up recorded video to hot-roll live which helps tell the story, keeping our fingers crossed the live TV signal from the chopper to the viewers homes stays locked are some of the details behind the scenes of the live report you see on-air. When everything goes smoothly it’s a beautiful symphony, but with so many links in the chain anything can go wrong and it is common. Then I have to ad-lib while I quickly work out the problem live on TV while making it seem natural. We fly everyday and produce a bunch of aerial television so we get a lot of practice.

I was a television news photographer on the streets for 13 years winning 15 Emmy Awards before I learned to fly the helicopter. Those years of experience working on the ground really helps me in the air, I understand the big picture and where we fit in.

A highlight in my career was recently flying actor/comedian Will Ferrell and dropping him off in center field during a baseball game for the HBO special “Will Ferrell Takes the Field”. The final approach into the stadium could have been stressful but Will was so cool, he made the landing fun. The beauty of my job is that I’ve never had to work a day in my life, I’m fortunate to have chased my dreams… and caught them.”


Jen is the shit. She’s funny and smart and intellectual and a potty mouth and a bunch of other great things. I’ve worked for her in little bits and she’s always been friendly and attentive.

She’s a veteran comedian, a New York Times best selling author, actor, writer, and has a new special on Netflix. She’s a perfect example of a creative professional and because of all that I also assumed she’d have valuable insight on stress in the creative process.

What part of your creative process causes you the most stress or anxiety?

“The most terrifying part of the creative process is that I don’t schedule time to be creative. I don’t sit down from nine to five in a coffee shop to “write jokes.” My jokes just come to me. I write about my life so I should say that the way to talk about things in my life just comes to me. I’ll go through phases where I physically feel energized and my head feels full – like if somehow a head cold could feel good – I feel foggy and stuffy and full of ideas that have to come out. I’ll usually take walks or just be in my apartment with lots of coffee and wait. And when things start to shake out of my head I make notes. Wherever I am I make notes. I’ll write them on paper or I’ll put them in my notes section of my iPhone. Words and phrases like “Mom met Paula Deen” or “eggs assault small talk” that make no sense to me but are at least five minute stories that are very intricate.

So, when those moments of inspiration DO NOT COME for a while – I worry that I’ll never think of anything funny again. I beat myself up for not being the type of comic who sits and writes every day and I feel it’s too late to learn and I don’t want to learn and I then I start spinning out. No one would know I’m spinning out – this is all done in the privacy of my head.

And eventually the writer’s block is over and more thoughts come to me – and then I’m back to thinking I’m so divinely inspired totally forgetting that a few minutes earlier I thought I was a piece of shit who doesn’t know how to write. And this repeats forever basically.”

Was this decision right? The stress and anxiety that goes along with creative professions is complicated.

More info on Jessica at
More info on Bruce at
More info on Jen at
Header image by Brett Mikoll, and Derek Gabryszak.

Thanks for reading Question Market 4,


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,


Go. Ready. Set.

Art classes never felt creative to me. I was never lit up by the task of drawing a bowl of fruit accurately. It wasn’t until about half way through high school that the creative challenges within graphic design made me feel like I could pull a rabbit out of a hat.

Several years ended up passing before I was properly satisfied with a visual problem I had attempted to solve. There’s always that first one.

I asked Brandon Schaefer, Open Mike Eagle, and Al Madrigal what they considered to be among their first successes as creative people.


Brandon is an incredible graphic designer who primarily designs movie posters. Brandon fascinates me because he so consistently remains a student of the movie poster and design game and that comes through in his work.

He’s created great images for some great projects and people. He is the creative director for Jump Cut, an entertainment advertising agency, and explores the world of his chosen profession on a podcast he co-hosts called The Poster Boys.

What do you consider one of your first successes as a creative person?

“This might sound silly, but it was something really small that felt quite big at the time. During my senior year of high school, I was asked by my design teacher if I wanted to design the program for my class’s graduation ceremony. The details are hazy – it’s been over a decade – but I remember how excited I felt to be given the chance to make something that would be seen by a lot of people.
For the next week or so, I spent a little bit each day after school teaching myself how to really use the pen tool in Illustrator. The first Spider-Man film was hitting theaters around the time, so I drew him web-slinging underneath “Class of 2002” with a graduation cap and a diploma in his hand. It was a pretty simple black and white illustration that was printed on a folded sheet of blue office paper…honestly, nothing incredible about it – but seeing it printed and in everyone’s hand felt like a tremendous accomplishment. I’ve been lucky to have worked on a lot of great things since, but I don’t think any of them have touched me in quite the same way as that first experience did.”


Mike is a rapper from Chicago. I’m fascinated by the depth of Mike’s releases and output. He has a storyteller persona more than the persona or function that many rappers/MC’s traditionally take (to keep a party going, or defeat an opponent). I feel very few degrees of separation between him and his music, even when he’s not referring to himself at all.

I wasn’t able to connect with him properly for artwork on his latest album (“Hella Personal Film Festival”), but am thankful he gave us the following peak inside his brain and story. Thanks, Mike.

What do you consider one of your first successes as a creative person?

“i would say that my first success as a creative person came when i won my first rap battle in high school. I didnt really have much to hang my hat on socially before that point and becoming part of the skills based community of underground hip hop was really big for my self image. But actually progressing to the point where I can win a battle was a big turning point. I was like I had gone from ‘I can do this’ to ‘I can be great at this’ and I hadnt had anything like that in my life before. And realistically I havent looked back from there.”


Al is a stand up comedian, actor, and entrepreneur. I’ve worked with him on and off for years and am reallllllly glad he said he’d answer my question. Al is interesting because he wears many different hats so effectively.

He’s been a contributor to The Daily Show since 2011, and co-created the All Things Comedy Network. His ability as a comedian is obvious and it’s where he’s dedicated, but I’ve always gotten the sense from him that he’s interested in the inner workings of all the other worlds he gets exposed to by doing comedy. Television, film, design, business, family, politics, technology…etc…

What do you consider one of your first successes as a creative person?

“After spending three years a mute in high school, I finally decided to run for study body treasurer my junior year. My first creative success came with my campaign posters and speech. The posters were all very detailed and fun – “Ask your mom” (Along with a variety of older mom ladies) I’ve always been relatively comfortable with public speaking but when I had to do the speech for study body treasurer at 16, my junior year of high school, that was instrumental at developing my comedy career. It was the first success I had at being funny in front of a crowd. I don’t know what possessed me, it was 1988, but I thought it would be funny to do a Jesse Jackson impersonation. It was Jesse Jackson’s second presidential campaign, so very topical.  Super hacky but my speech rhymed and the impersonation seemed to be on point. I talked about “fiduciary responsibility” and such.., it killed. I remember afterwards the vice principal pulled me aside to tell me that I won in an absolute landslide. I got 1200 votes out of 1300. The guy I beat out ended up transferring out of the school.

Because my speech for study body treasurer was so successful, Mario Prietto, S.J. then principal of SI, lobbied me to be the salutatorian for my senior year.  Back then, at my school, salutatorian was not given based on academic accomplishment. Huge honor, because salutatorian was chosen based on who was funniest and would give the best speech. I did a light roast of the entire 1989 class and did an impression of Mario Prietto. That’s when I got the bug, my first creative success.”

The confidence gained by those first experiences is so interesting to me. It’s a real world application of something that each of us have long suspected. It’s gaining access to a room we’ve always wanted to go in.

More info on Brandon at
More info on Mike at
More info on Al at

Thanks for reading Question Market 1. I’m working hard to bring another one soon.



%d bloggers like this: