New Riders San Francisco

TO INSIGHT, SURVIVAL, AND ARTISTIC FULFILMENT — 144 pages, 5 x 7 in. (12.7 x 17.8 cm)

All my books come into existence because I’m trying to process something about my life. All Access was about trying to figure out if I wanted to go on being a graphic designer. 100 Days of Monsters was my attempt at creating a time capsule of the amazing birth of the Daily Monster experiment. The Graphic Eye lived at the intersection of vanity and insecurity, making amateur photos into a beautiful coffee table book. And You Deserve A Medal was my ludicrous attempt at making sense of love. 344 Questions wraps up all of those books into one.

It’s about life as a creative person. It’s about determining where you are, where you think you want to go, where you actually want to go, and what’s stopping you from heading in that direction. It’s about art, design, vanity, insecurity, pretty things, love, panic, and hopefully about action. Hell, maybe it’s even about redemption.

All of it in the form of questions. Why?

In my ongoing effort to become a better artist, designer, writer, illustrator, home organizer, lover, gardener, friend, traveler and all around great person, I’ve read a fairly frightening stack of self-help books. The books that turned out to be most helpful were those that found me at the right moment. “How many psychiatrists does it take to change a lightbulb? One, but the lightbulb really has to want to change!” But even the better books often put me off—by using cringe-inducing hippie dippy language, and more often than not by relying on examples that had little to do with me.

An animated look at the opening spread.

Over the years I channeled that frustration into the 344 Questions poster, into my talks, and into the ink & circumstance columns. All Access also had a self-help aspect, of course. “What did they do? How can I apply that to my life?” With this book I simply cut to the chase. No more examples. No roundabout attempts at prescribing solutions. Just questions. How does that make you feel?

Aesthetically, I set out to make the book as fun and usable as possible. It’s a small format, so you can carry it with you like a sketchbook. The flexi-binding makes it hardy, but won’t wreck your bag or pocket. There’s a page marker ribbon, with which to tie up your miniature horse. And the flowchart layout hopefully makes it fun to look at and fill out. My ideal version of this book is dinged up, dented, worn on every surface, and fully be-scribbled by you, with a rubber band around the whole thing to hold extra sheets and magazine clippings. When it looks like that it’ll be your book, and that’s what I want to see.

I sweetened the deal with extra questions by some pretty brilliant celebrity inquisitors. The lineup is half autograph collection, half family album: Judd Apatow, Patton Oswalt, Wayne Coyne of the Flaming Lips, Dave Stewart of Eurythmics, Tarsem, Sagmeister, Marian Bantjes, J.J. Sedelmaier, Ze Frank, Christoph Niemann and many more! Doyald Young was quite hesitant about taking part at first, but I’m so glad I browbeat him into it. His wise and generous questions close the book. Which is as it should be.


A great question from Dave Stewart.

Allow me to add a few behind-the-scenes notes on the making of the book: Publishing can be a battle. When your name is on the cover of the thing, every decision becomes personal; every detail is worth fighting for. This makes for a tough process. Some of my books were relatively easy to shepherd into print, others left me ready to check myself into the witness protection program.


Page 128 unplugged. In the book it’s full of Ken Carbone’s questions.

In every case there were at least a few moments of heated conflict—usually over the title or the cover—that led to outbursts of “Oh yeah? Fine! It’s all off then! Here’s your advance back! I’m taking my book, and I’m going home!” Sometimes book-suicide is the only leverage you have left. Whenever this happens I feel nauseous and embarrassed. Not for my outburst, but for the fact that I’m not trusted to make important decisions about my own idea. Beyond that, though, I’m angry at me that I couldn’t figure out how to engender that trust. It’s not how things should work beyond your teenage years. “I’m holding my breath until you give me what I want!” Surely, that can’t be the way it works, can it? But again, when it’s your book, you really can’t put the process over the result. The process ends, but that book will have your name on the cover forever.


Hey look It’s the whole damn book! Laying it out like this is so much more satisfying than keeping a little stack of paper on your desk. As long as I don’t accidentally move that chair…

Every time we’d come to a major decision point I’d ask, “Can you show me data that support what you want me to do? How much better do blue covers sell over green covers? Why did this book sell thousands of copies and this other one didn’t?” There are guesses, coincidences, but in the end it’s still all gut instinct. And then it’s their gut instinct vs. yours. It becomes a battle of wills. And every time I felt that the projects suffered because of it. Welcome to the “bitter author” section of the site.

The point of all this is that none of that happened on this book. Nikki McDonald and her team at New Riders just… well, they just let me make my book. What you see here is the one and only cover design I ever presented. It’s the one and only title I ever pitched. (The only change being that I switched it to “The Creative Person’s” instead of “The Graphic Designer’s” when it became clear that the book had a wider scope.) Nikki was happy to help me figure out issues as they arose, but in the end she always told me, “Hey, it’s your book.” I still get a little misty just thinking about it.


Yes, half of page 82 is intentionally upside down. You got a problem with that?

And here’s the thing: Not having to fight about every little thing made me work on it twice as hard. It’s much more fun to honor somebody’s trust than to fight against their lack of it. So I went all out, drawing up 130 pages of flowcharts, creating typefaces based on my hand-lettering (with the expert help of my colleague Tim Moraitis), and making it all fit together harmoniously. It took some time, but I’m really proud of the way it came out. (I’m still shocked that this is the cover that got approved.)


Happily, 344 Questions is turning out to be my best-selling book so far, so… yay! And phew! And Thank you if you already bought a copy or gave one to a friend! I hope the book is proving itself to be useful!


No matter how hard I try, some bonehead error always slips through. (I’m sorry, Jakob.)
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