Playing it safe isn’t good enough;
I have to try things that might fail

I was working at my desk on a recent Saturday afternoon when I noticed two cat ears poke above the surface of the desk. Then there were two intense little green eyes staring at me.

Bessie and her sister, Molly, are feral girls who I took in about seven years ago. They’re both tiny, weighing slightly less than five pounds. Bessie has only three legs and she’s never gotten over the fears she brought with her from that early life on the streets.

She runs if I get too close. It’s an ordeal if I have to touch her for medication or flea treatment. If I’m able to catch her to pick her up, I can feel her tiny heart beating very fast with fear.

Every now and then, it seems as though Bessie might get over some of her fears and trust me, at least a little. This was one of those times. She was sticking her tiny head over the edge of my desk and she seemed to be thinking of coming up onto the desk to see me.

She just stood there, though, and watched me.

Although I was able to snap a quick picture, she decided the risk was too great to trust me. She jumped back down and left the scary human alone. That wasn’t going to be the day when she got over her fears and took the chance of trusting me.

I thought a lot this past weekend about that moment with Bessie because the weekend marked 10 years since I poked my head above the surface of my fears and tried something that scared me. It was at Birmingham’s Sidewalk Moving Picture Festival in 2005 when my one and only film so far made its debut on a late-summer Saturday morning.

That was 10 long years ago. I looked my artistic fears in the eye by stepping up to try something out of my comfort zone — and then I stepped away from the challenge after that one film was finished. Instead of building on that success — and the success of the couple dozen festivals that also showed the film afterward — I ran away and stuck with safe things that didn’t require me to take risks.

• • •

When I was in college, I took a creative writing class. There wasn’t a lot of formal teaching. We were all just supposed to read things we had written — or were working on — aloud to the class and then we learned through group discussion what worked and what didn’t.

We were guided by a crusty old fellow who had been writing fiction professionally for years. He wasn’t subtle in his criticism and he didn’t have patience for people with no talent. You had to get his permission to take the class before you could even sign up. I was intimidated of him.

I was working part-time for a newspaper, so I took the easy way out of my writing assignments. I just read things I’d written for the newspaper. I read sports stories and news stories and features. Each time I did it, I could tell that the teacher wasn’t happy with me. He couldn’t criticize much about what I was writing, because everything was correct for the very conservative form of writing that I was doing.

I kept meaning to write some original work — fiction of some sort — but I never quite got around to it.

I participated heavily in the class discussions and I could tell that the instructor was pleased with my comments and insights. I could listen to my classmates and explain in detail what they were getting wrong and give compliments when they did things that were good. People started asking me for advice about their writing on the side.

But one day the instructor asked me to see him after class.

“You obviously understand how to write,” he started bluntly. “You understand story structure better than you should. Your mechanics are perfect. You understand characters and motivations like someone much older than your age. But the things you’re reading to us are junk, because there’s nothing creative about them. You have talent written all over you, but you’re not writing anything. If you want to remain in this class, you’re going to write good fiction, not read us the things you write for a newspaper.”

I told him I understood and that I wouldn’t bring any more newspaper stories to read. Then I left.

I dropped the class and never returned. I ran away rather than taking the chance of exploring unfamiliar territory and taking the risk of writing something that I wasn’t certain how to do without being criticized.

• • •

Although I’ve taken chances with business ventures in my career, I never really took artistic chances. Business risks seemed safe and acceptable to me. Even if I failed — and I did have a major failure at the age of 29 when a newspaper I founded failed — I wasn’t concerned about what people would think. But I played it safe when it came to creating anything truly original.

I started in a field where you didn’t take artistic chances. At various newspapers, I filled “creative” roles as a writer, photographer, graphic designer and editor, but none of those involved artistic risk. A newspaper almost always plays things safe. You need everyone to like what you do, so you make content that’s safe, predictable and inoffensive — pretty dull — something so disposable that it’s used to line bird cages and dog crates.

Everything I’ve done over the years has been with one eye firmly on the crowd. I didn’t want to care what people thought of my work, but their reactions had a large degree of control over what I did next. I wanted people to love me and approve of my work. I did what was safe — in order to get their approval.

When I started this site, I still played it safe by concentrating on current politics and libertarian ideas. I didn’t know what I wanted to talk about. I had been wanting to write for public consumption again, but I didn’t know what I wanted to say. I wrote about politics because it was easy and safe. Then I slipped into playing to the crowd — giving them red meat.

(I went back this week and read some of the things I wrote in the early weeks of this site’s existence. The articles were bland, boring and clearly lacked direction. Even though I knew how to write, I had no idea what I was trying to accomplish in those early days. I was playing to the crowd and begging to be loved.)

Even when I made my short film a decade ago, I played it safe by writing a parody — something that would consciously copy the voice of another style — rather than doing a narrative that had to find its own voice. Maybe it was justified at the time — because I didn’t have the budget to hire actors to pull off something truly original — but I still gravitate toward making things like that even today, because it’s what I understand how to do without taking much of a risk.

It might even be justified for me to copy another style as parody for awhile as I perfect what I’m doing. I’m not sure. But I do know that even if I made another film or two like that, I have to move beyond those artificial constraints and do something more difficult — something original which reflects my own creative vision.

Writer and marketing guru Seth Godin says you’re not pushing far enough with your work unless you find yourself saying, “This might work. This might not work. I just don’t know.” (Listen to “Leap First: Creating Work That Matters,” if you’re interested in his thoughts. They’re worth listening to and thinking about.)

If you do something because you need to be sure it’s going to work, you’re playing to what you know the crowd wants. That’s going to be generic and probably boring. People might tell you they like it, but it’s not art. It’s not original and it doesn’t have a real chance to change anyone.

At this point in my life, I’m going to have to take artistic and emotional risks. I’m going to have to step outside of my comfort zone if I want to have any chance of becoming the artist and the person I know that I need to be.

I’m not ready to do that. Seriously. It’s a game I play with myself, a sort of bargaining to avoid doing anything that matters. Intellectually, I believe I have the talent to make some decent art, but emotionally I’m terrified of risking failure and ridicule.

Here’s the truth. I’m terrified emotionally that I might have no talent, so I will use any excuse to avoid doing the things I say I want to do — for fear that doing those things would expose me as a talentless fraud.

So I keep telling myself that I’ll take creative risks one day — when I’m finally ready. When I’ve finally learned all I need to learn.

For years, for instance, I’ve wanted to make a podcast, but I’ve never been ready. I wasn’t sure what I’d talk about. I didn’t know enough about the recording and editing process to make it sound professional from the beginning. So I’ve just continued to say that I’d get around to it one day — when I was ready.

For a bit more than a year now, I’ve listened regularly to a history podcast from an anonymous college history teacher who just calls himself Prof CJ. He calls it the Dangerous History Podcast. At first, I thought the show was terrible. The first few episodes were very uneven. The production quality wasn’t good. I didn’t think he knew what he was trying to accomplish at the time. I almost quit listening.

But a funny thing happened over a year. Prof CJ got comfortable with what he was doing. He settled down and found a focus. He learned how to make audio that sounded professional. He’s doing really good work today and I recommend his podcast regularly to others. (His recent series about the American Revolution, for instance, changed the way I saw that war, even though I thought I already knew pretty much everything to know about the overall narrative of the revolution.)

In June, he reflected back over his first year of podcasting and shared some numbers with his audience. He admitted that he didn’t know exactly what he was doing in the beginning. In his first month, he was putting out two new episodes every week, but in the entire month, he had only 147 downloads. Total.

He clearly wasn’t ready for what he was trying to do. And his audience wasn’t exactly begging for more yet. Almost nobody knew his podcast existed. But he kept it up, ignoring his early ignorance and uncertainly.

This past May, he had 15,865 downloads, more than 100 times the number he had that first month just a year before. By doing what he wasn’t ready to do, he had become successful and I expect to see him become even more popular.

What if Prof CJ had continued waiting until he was “ready”? What if he kept waiting for someone else to give him “permission” to do his work?

I like playing it safe. That’s what my training and my programming make me ready for. But if I want to matter to anyone — and be authentic about who I am — I’m going to have to push myself and take some chances.

It might work. It might not work. I’m going to find out.

• • •

I read a book a few years ago called “Why Everyone (Else) is a Hypocrite.” In the book, evolutionary psychologist Robert Kurzban explains how the human brain has developed over the years and how its structure makes us do otherwise inexplicable things today.

Kurzban explained that different parts of our brain are competing with one another. What’s worse, some parts aren’t even capable of communicating with one another. We like to think of ourselves as a unified “I,” but the truth is that every person is a collection of warring interests inside — with each part competing for the driver’s seat.

The more ancient part of our brain — which some have called the “Lizard Brain” — wants certain things. It doesn’t like risk. It wants basic needs met and tends to be pretty fearful. We have various other parts of our brain that want entirely different things, but I want to mention just one other part of my own brain.

I call that “person” in my brain The Artist.

The Artist has a desperate need to create. He’s not really concerned about risk. He just has a hunger to express ideas and feelings about life and beauty and passions. He needs to make things. He doesn’t care about money or safety. He just needs to express thoughts and feelings that are incredibly important to him.

And you can see the conflict. The Artist wants some clearly defined things. The Lizard Brain wants entirely different things.

The Artist refuses to allow Lizard Brain to get what he wants. The Artist refuses to allow me to peacefully do the kind of boring work that everybody else does. He goes on strike like a petulant child at times. He says it doesn’t matter what Lizard Brain needs. He says if he can’t have what he wants, he’s not going to allow anything to happen. He’s temperamental and needy.

Lizard Brain isn’t terribly sophisticated. He doesn’t have the understanding of higher reasoning and deep feeling that the Artist does, but he does know that pursuing what the Artist wants is dangerous. What’s more, he knows that it’s useless. Art doesn’t matter to him. All that matters is accumulating resources in order to be safe and provide for “us,” plus the cats and a future family. That’s all that matters to him. And whenever the Artist attempts anything, Lizard Brain squelches it with fear — deep, primal fears related to failure and loss.

How can this conflict finally be resolved. Can I do anything about it?

Next in Part 2: “Honest art builds bridges for aliens who crave connection with humans“