Creative work is about boundaries of time and boundaries of space.

Last week, Austin Kleon, the Texas-based “writer who draws,” helped kick off SXSWi with an opening keynote on creativity, inspiration and innovation. Kleon discussed themes from his latest book, Show Your Work!, which outlines how everyone—not just creative types—can put their work out into the world. His best-known book is Steal Like an Artist, billed as a “manifesto for creativity in the digital age.” We interviewed Kleon while researching our 2012 report Play As a Competitive Advantage, discussing the role of play in our highly structured world. Among other things, he talked about why creativity requires confidence and a willingness to look stupid, and why “the really smart agencies are the ones that say, ‘We want you to fuck up.’”

Tell me about your background as an artist and how you came to the place you are today.

My early years were basically tons of unstructured time, and I was able to keep this my whole life. Because I lived in a rural area, I didn’t hang out with other kids all that often. I had my own kind of studio in the back of the house. When I got home from high school, I would play music, write, read or whatever for hours until my mother came home.

When I went to college, the restrictions started coming in. One of the things I noticed is that the subjects start to separate even more. You’re supposed to be an art major and do art, or you’re supposed to be an English major and do English. I thought English was the more serious thing to do, so I put all my energy into writing and English. Then toward the end of college I figured a way to weave pictures and words back together. After I got out of college, I got a job as a reference librarian. It was a part-time job, so I had that unstructured playtime again. And that was when I started making my newspaper blackout poems.

A few years later I got a full-time job as a web designer at the University of Texas School of Law [in Austin]. My unstructured playtime got zapped a little bit, but what I found was that the bus ride to and from work and then my lunch break were the perfect time in which to do that play again. I wrote my first book during those bus rides and during my lunch breaks. I did that for three and a half years. Then I got a job as a copywriter at an interactive marketing agency called Springbox. That was the closest to a full-blown “creative job” I’ve had. While I was working there I took a weekend off to go give a talk that led to Steal Like an Artist.

Almost the whole time I worked at Springbox, which was only a year or so, I was working on either writing a speech for Steal or turning it into a book. When the book came out I knew I was going to be sent on a 20-city tour, so I left my agency job. I’ve had these two timelines that have finally merged into this little career I have now.

It’s interesting that you segued your way into being a full-time artist.

A lot of that was based on the fact that I’ve worked a day job for more than half a decade. I’m also incredibly cheap, and so is my wife. We save money, and we live in a really cheap place in Austin. So I have the financial freedom now to give this a shot. What’s interesting about having a day job is that it becomes clear when you have those times to get your own work done. You’ve got an hour, and you’ve got to get something done.

How does play fit into the workplace and into agency work in particular?

My personal opinion of play is that it’s very simple. You give someone a space, material, time and no interruptions. That’s pretty much all there is to it. There’s a really brilliant lecture by John Cleese. He says the same thing, that creative work is about boundaries of time and boundaries of space. My personal experience of working at a creative agency is they’re just not set up in a good way to do that kind of work.

My agency in particular, it was an open office space, so you never had any privacy. You never had a space you could call your own in which you could put things up on the wall and surround yourself or cordon yourself off. There’s always tons of meetings interrupting your day. You were constantly expected to answer email. I had a creative director yell at me because I wasn’t on Instant Messenger constantly. I would explain, “If I’m available, then someone’s going to bug me and I won’t get this work done.”

It’s not anything new, either. Look at David Ogilvy, who said something along the lines of, “I never wrote a good ad at the agency. I always went home where it was quiet, where no one could get at me.” That’s when he came up with his good stuff. There are some people like Jonah Lehrer, in his book Imagine, and Susan Cain, in her book Quiet, who are showing that this whole idea of social creativity, brainstorming or group think is kind of a myth. We’re stuck in this way of operating that doesn’t lead to the best kind of work.

We’re only starting to question, “Hey, does brainstorming really do what we think it does?” The problem with a lot of agencies, they’re really big and things have been done a certain way for a really long time and it’s hard to change the operating pattern.

Do you see the youngest generation defining creativity in new ways? Does digital sharing count as “real creativity”?

I think what you’re seeing with this new generation is that their idea of creativity is a bit more open. This whole culture of remixing and mash-ups has lead to this collective creativity; it’s more of a collective activity.

What I do see becoming part of a healthy lifestyle, and something I advocate for in my book, is a digital-to-analog loop. You structure your time in a way where you’re getting what you can from the digital world. You connect with people and you read what people are doing. Then you walk away from it, process it and have your scheduled playtime. You create something with your hands. You take that and put it back in the digital layer and you push it out to people. So the whole process goes into a loop.

People have to consciously do that now. There needs to be a rallying cry to step away from the screen. People are going to have to consciously schedule nondigital time. It comes down to what John Cleese talks about, that boundary of time and boundary of space. Of course, when you have the Internet in your pocket, that space boundary and that time boundary is really difficult to navigate. On the other hand, perhaps the new generation will have something to teach us about creativity.

When a new tool or technology comes around, I think it is the job of artists and people who do creative work to show what a new tool can do. I’m thinking about something like the iPad. When it came out, no one talked about how it was a tool for creation. And that’s obviously been completely turned on its head. An artist like David Hockney, who makes virtual paintings on his iPad, is a really great example of that. His iPad work has even been displayed in galleries. Everyone pooh-poohs Instagram, saying it’s all about vintage nostalgia or it’s just a network of people mindlessly sharing pictures of their coffee in the morning. Those two things do exist, but there are people who are doing incredible things with Instagram.

The first thing they teach you in photography class is to carry your camera everywhere. What something like Instagram does is it trains people to think about, “That would be a really great Instagram shot.” People are looking at their world closer and being more actively engaged in it. They’re looking for that good shot. You’ve got a whole group of people now that’s being more creative because of this tool that everyone thought was stupid.

In your opinion, is there a difference between a creative person and an artist? Especially now, when we have tools like Instagram, does it matter how people label themselves?

I think that’s a good question. Picasso said, “All children are artists. The problem is how to remain an artist when the child grows up.” That’s always been one of my favorite quotes. “Art” and “artist” are words that are loaded with all these meanings. I think the loftiest thing that [marketing work] can do is actually turn people into creators themselves. Turning people into active participants in their world instead of these consumers.

One of the reasons people love Apple is because Apple products help you do things. The bottom line is, a lot of products don’t help you do anything. Right now everyone has the tools to do art, to do creative works. The tools have gotten very cheap. The tools for sharing work and finding an audience are even cheaper. What we’re dealing with is the fallout from the way things were done. The people that have normally held the gatekeeper keys don’t want you making art. A lot of artists don’t want people to be artists, because then they’re out of a job. It’s self-preservation.

In my own career I’ve discovered that helping people find their creativity and become artists can make for a more lucrative career than just standing or sitting on your pedestal and saying, “Oh, I’m the artist. Look at me.”

[People] want to be engaged. They want to manipulate their world. They want to have a say, and you have to figure out how to give them a voice. On the other hand, there are a lot of businesses that don’t want that, and they don’t get that. They don’t want people to be able to say whatever they want about their products and do whatever they want with their products.

Do you think there is any correlation between being comfortable in your skin, being confident in yourself, and embracing creativity and play in your life?

Absolutely confidence is part of it. And confidence is what we lose right around middle school. John Cleese lays this out. He says we need faith, time, confidence and humor. Little kids have confidence. You give a 5-year-old a crayon and a piece of paper, that 5-year-old will draw you something. You give a 13-year-old a piece of paper and a marker, and good luck. They have that idea already that they’re not an artist, they’re not a creative person.

I think it’s social. You get to middle school and there are probably people who get blue ribbons for their art and people who don’t. We’ve already set up this system in which there’s good art and there’s bad art. And there are people who are artists and those who aren’t artists. There’s people who are creative and those who aren’t creative. It’s not even the confidence in your abilities. It’s the confidence in knowing that you don’t know, that you’re not good but it doesn’t matter.

There’s a certain confidence that comes from unstructured play: “I don’t know what I’m doing. It just feels good. I’m just following this thing until it tells me where it’s going.” A lot of people can’t deal with that, because the whole world sees it as, when you go to kung fu lessons or violin, at the end of it you’re supposed to be better or you become a professional at this thing.

The whole thing about creative work is you just don’t know what’s going to happen, you can’t even guarantee that you’re going to have a final product. But you have to have the confidence. Donald Barthelme said, “There’s a thing in art; it’s not knowing.” And it’s the willingness to accept that you don’t know where you’re going that leads to the really great creative work.

I have a little checklist in my book of things you’ll need, and one of them is a willingness to look stupid. When you go to a concert, everybody’s got a camera, everyone’s a photographer. When I was younger, I started going with a sketchbook. You would not believe how much attention you get if you’re standing at a concert with a sketchbook. All of a sudden everyone wants to look at you. They want to see what you’re drawing. They think you’re some weirdo. You have to be willing to not care or be completely nuts.

Creative jobs are tough too, because they’re based on what you bring out of that room. If you think about that when you’re doing it, the end result is not going to be good. You have to be able to shut that down and think, “I don’t know what I’m going to get out of this, but I’m going to work at it.”

What’s great about being an artist is you can pretty much go into your studio every day and do your work. Then whatever comes out at the end of the week, you can figure out how to market and sell it. Whereas if you’re an art director or a copywriter, you have a client and they have a business goal. You have to use a little bit of your creativity to sell that business goal for them. It is a completely different thing, but it’s still creative work.

With a lot of creativity you need to not know where you’re going. You need to not know what the end stage is in order to get somewhere new.

Chapter nine of your book Steal Like an Artist, “Be Boring,” stuck out to me. Can you talk a bit about that?

This is the one everyone gets hung up on, and it’s the hardest one for creative people to deal with, because it’s very much against what we think of as creative people. When we think of creative types, we think of Don Draper having a three-martini lunch, chasing after coeds. But you never see Don Draper do 50 drafts of an ad. You never see the actual work. And in a lot of artists’ biographies, you never see the actual work or the actual sitting down every day and getting the work done. What that chapter is really is a take on this Flaubert quote where he says, “Be regular and orderly in your life so you can be violent and original in your work.”

What that comes down to is that creative work takes a lot of energy, and you don’t have that energy if you waste it on other things. There are a lot of things that creative people don’t feel like they need to bother with in their lives, such as taking care of themselves. A lot of creative people don’t realize that your body is one of your tools, and if you don’t take care of it, it’s not going to be a good tool. A lot of creative people don’t want to deal with money because they think that that somehow cheapens their work or it’s beneath them or whatever. But monetary freedom equals creative freedom. The chapter is about being boring in your everyday life so you simply have the time and energy in which you can actually do the interesting, exciting work.

People always ask me, “How does Austin, Texas, inspire you? How does Austin inspire your work?” I always reply, “It’s the fact that Austin doesn’t inspire my work that actually makes me like living here.” I don’t find myself inspired to make things because of Austin. What Austin has is really cheap real estate. Basically, Austin’s a pleasant place to live. For me, Austin is kind of a boring city in the best way possible. A good night out consists of sitting around outside drinking beer, eating food, and that’s it. There’s not a bazillion things to do. That’s what I’m comfortable with. I don’t feel like I’m constantly missing out on things.

This is why I love, love, love the Internet. I am friends with so many people in New York, but I don’t have to constantly schmooze with them. I get fellowship with them online. And then when I’m in town, I can take them out to dinner or whatever, but I don’t have to be completely saturated with that social scene. I like being out a lot, but I also know that creative people need a lot of time to sit around and do nothing. That’s how you get your ideas.

What can adults learn from kids about creativity in play?

Adults have been kids, so they know what it’s like. They’ve just lost touch with it. What kids can do is put you back into that feeling of what it’s like to play. Playing with children in particular can give you insight, because kids are very structured with their play. They make up little rules for themselves. Its funny, when I play with my nephew, he’ll tell me all these rules. Kids can teach adults not to take themselves so seriously, which is a huge part of what I think creative work is about. It’s about having that sense of humor.

I also think kids can teach adults to embrace not caring about where this is going. It’s that willingness to build something for the hell of it and then be OK with just destroying it. It’s so powerful for kids. Adults, especially creative adults, need that. They need to be able to build something for no reason, then tear it down and start over.

All of this is great for our personal happiness and development and growth, and especially for creative people to become more creative. But how do you apply that to business as a whole? I feel the billing structure is a huge roadblock. You have to be willing to throw out everything you’ve come up with so far in order to push into that thing that’s really going to get to the business goal. The first idea that occurs to you might work, but you have to be willing to destroy that idea and go further into something new to really get the best solution.

There’s a designer named Mike Monteiro, who wrote a book called Design Is a Job. I heard him say one time, “Innovation is not a goal. Selling pants is a goal.” Selling pants is a business goal. Innovation is a byproduct of selling pants better. The trouble with creative work in a business setting and even in a cultural setting is, if you come up with something truly original or far out there, people don’t know how to deal with it. They won’t be able to accept it because they don’t have any kind of reference point.

That’s true in classrooms. That was another good point of Jonah Lehrer’s book. If you ask teachers what they want in students, they’ll tell you, “We want more creativity.” Then when you ask them who their favorite students are, they are students that behave, that don’t ask hard questions, that follow lesson plans. It’s actually the uncreative kids that teachers like the best, because they cause the least problems for them.

It’s true in an agency setting, too. The people who get along really well are the people that are able to come up with decent solutions that don’t rock the boat at all. The really smart agencies are the ones that say, “We want you to fuck up. We want you to make mistakes. We want you to tear our thing down and build something new, ’cause we know that’s where the really good work’s going to be.” In execution that’s really hard to do in the work setting when you’re worried about your job and what’s going to happen to you.

Bosses say the same thing as teachers. They say, “I want creative thinkers. I want people who think outside the box.” But when they get someone who causes friction, who questions conventional leadership, it can get very difficult. And it takes a really secure, confident boss to say, “You’re right. Let’s try this.”