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 seekandspeak.com.
More info on Mike at mikeeagle.net.
More info on Al at almadrigal.com.

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



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