Chapter 41: Risky Business

In the pantheon of gratuitous writing advice, alongside write what you know and find your voice, is the admonition to take risks. 

Often this advice comes from writers who look back at the risks they took when they were young and unknown. Fearful though they might have been of more rejection and failure, they nonetheless were bold enough to take risks that would result in their becoming so successful that they could counsel young writers to do what they had done. 

In fairness, the advice is well intentioned and generous. But it is often maddeningly vague. It suggests that risk taking is one-size-fits-all, that all risks are the same: just take a deep breath and leap. But risk is a deeply personal act. To see it any other way, to model your writing life on the risks that someone else took, is as foolish as building a career by imitating another writer’s voice.

Is it good and necessary to take risks as a writer? Of course. But what kinds of risks? And how to assess the wisdom of those risks? Is this a smart risk or a foolish one for me? What is the upside and what are the pitfalls? The questions, the necessary questions, do not stop there.

The best story about risk taking I have heard in a very long time comes in the terrific music documentary Muscle Shoals. It is the story of a small recording studio in a tiny Alabama town where a white producer, Rick Hall, and his young white session musicians helped shape the careers of scores of legendary musicians, many of color, among them Aretha Franklin. 

Aretha’s story is a parable about risk. It begins at minute 36 of Muscle Shoals and although I am going to tell you what happens, you really have to see it and more importantly hear the music in this story, which goes like this: It is 1966. Aretha is 24 and her career has stalled. Her label, Columbia, drops her. But Jerry Wexler of Atlantic Records sees great things in Aretha. He signs her and sends her to Muscle Shoals to see if Hall and his musicians can help her find her path.

She is not happy when she arrives in Muscle Shoals. The musicians sense this and give her space. They try this song and that but nothing works. The studio is silent. And then, the keyboard player tries something different. Aretha listens and begins to sing and in that moment, down-on-her-professional-luck Aretha Franklin begins singing I Never Loved a Man and becomes...Aretha. The moment gives me chills, for the music as well as for seeing and hearing the transformation unfold. You cannot help but think that only from failure and from a willingness to take a risk born of that failure, could this have happened.

Before you race ahead and tell yourself I know failure. I know rejection. I want to be bold too and do what Aretha did, catch your breath and take a closer look at that story. Yes, Aretha is failing professionally and yes, she is taking a risk by embarking on a new path in her career. To succeed she has to be willing to risk failing again.

Aretha does not show up alone in Muscle Shoals and beg Rick Hall to let her sing just one song. You’ve seen that movie and this is not it. If Aretha cannot find her voice at Hall’s studio, the failure will be hers alone. Wexler has other musicians at Atlantic whom he will send to Rick Hall. Their careers will go on. She will be destined for singing in casino lounges before the headliner appears. 

But Aretha is in that studio because she has convinced Jerry Wexler and by extension Rick Hall that by virtue of her talent, it is worth their while to take a risk on her, to share in her risk. 

There is also something more at play in that roughly three-minute chapter of Aretha at Muscle Shoals: it is not one risk being taken, but two. One is artistic; the other is commercial. While they ultimately intersect and overlap, they begin independently. And it is in those separate moments, I believe, where the most useful lessons about risk lie.

The commercial risk cannot happen without the artistic. The artistic risk is useless if it does not find a way to be commercial — no man but a blockhead, said Samuel Johnson, ever wrote except for money. By commercial I mean a process that begins with showing your writing to someone else. That simple act comes with great risk — what if they don’t like it? But before it happens, before you take your writing public, yes to the marketplace, there is the often solitary work (sorry, but writers seldom have a keyboard player sitting nearby giving them a prompt) of bringing places, people and ideas alive solely by the power of your words.

That is not easy, and nor should it be, not when you have ambitions for your writing, creative and intellectual ambitions.

Easy means comfort, which comes when you are doing what you’ve done many times before. Anyone who has ever worked in a newsroom and covered a beat knows what I mean. The first few times you cover a story you worry about getting it right because the subject is new and you are new to it. You do it for a while and one day you realize you are writing the same story you wrote the day, and week, and month before. You’re just changing the words; it’s as if you were playing Mad Libs, except you’re not doing it to make the other kids at the birthday party laugh. 

If you find comfort in this, if you are like the reporters I knew of in Chicago when I was starting out who covered the same beat for 30 years — City Hall, the Cubs, cops, it made no difference, they were lifers on those beats -- then to my mind there is little to recommend in that writing life other than the prospect of a decent night’s sleep. 

Aretha wanted more. What more looked like, she admits in the documentary, she does not know. She only recognizes that who she is as a singer before Muscle Shoals is not it. I suspect you are reading this thinking you know exactly what she means. You also may feel as she did — not knowing how to get there. So Aretha does the only thing a creatively ambitious person can do: she experiments.

I once asked a scientist friend what the failure rate was in his lab. Eighty percent, he said. He did not say this with embarrassment or shame. It was to be expected. Yet writers too often assume that an eighty percent failure rate is akin to a constant reminder of their woeful limitations. 

Can I just say as someone who has spent too much of his professional life thinking this way: that is really dumb. I understand why it happens: we sit only a foot or two away from the scene of our failure — the screen, the page. We do not have the long view of an experiment that takes place over time and involves many people. It is just us, in that moment, with our eyes and hands and thoughts and that unforgiving page reflecting back our limitations. If we fail we have no buffer, no hand on the shoulder, no company with whom to share our failure.

And in that dispiriting moment a choice presents itself: Go safe or go big. Safe is welcoming. Safe is like a visit to the “Bunny Planet,” the children’s book about a place where all the bad things that happened over the day never occurred. I know successful writers who prefer this path. I cannot criticize them. At times I envy them, especially when I am checking WebMD to see if I can take a second Pepcid for my rumbling gut. The choice is a matter of temperament. Safety has its advantages but I have come to believe it comes at a price: a limit to how good you can ever be. Too little ventured; too little gained.

The risk is in the decisions you make, which is expressed in the way the words work together. Or not. Which is why it is perhaps best to think not like a writer, who sees each failure as confirmation of doom. But rather as a scientist, who assumes that four out of every five decisions may be the wrong ones but are hardly useless. They give a scientist insights and wisdom. Just as they can for writers.

Toni Morrison, in fact, drew much the same analogy. “As a writer, a failure is just information,” she once told an interviewer. “I recognize failure — which is important; some people don’t — and fix it, because it is data, it is information, knowledge of what does not work.”

She continued: “It’s as though you’re in a laboratory and you’re working on an experiment with chemicals or with rats, and it doesn’t work. It doesn’t mix. You don’t throw up your hands and run out of the lab. What you do is you identify the procedure and what went wrong and then correct it. If you think of it simply as information, you can get closer to success.”

It’s as simple and overwhelming as that. Try. Fail. Try. Fail. Try. Fail. Try....

It is Aretha at the piano at Muscle Shoals, playing cords that lead nowhere. Another and another and another. She is upset and the musicians are afraid to talk to her. You see it in her face, dead eyes. 

Then, something new. A riff. She seizes it. It has taken Aretha Franklin forever to arrive at this moment, an odyssey of failure and rejection and despair and all the while belief that she and her music are destined for more.

She starts to sing.

Next time, Part Two: The Commercial Risk