On Risk in Writing

“Think about your family, you dolt.”

This is the kind of mean-spirited personal attack that every blogger dreads. It was left four years ago on a blog post I wrote about the risks my wife and I were taking when we decided that I would leave the corporate world and she would quit her teaching job so we could start a small business at the very same time we were starting a family, too.

The company I started helps writers understand how to connect with readers so that when their book hits the shelf, it has a fighting chance of being read. After working with hundreds of writers, I have come to understand that I work at the intersection of creativity and risk—that terrifying place where you feel compelled to share something with the world, and in doing so, move away from emotional, personal, and professional safety. Writing and publishing a book, after all, is a bit like coloring outside the lines of expectations that people have for an adult life. It can play with traditional ways we categorize someone: no longer a job title or name on a business card, but now “a writer.” It is an identity that BEGS further questions, and oftentimes, judgment. You know the responses, I mean:

“Oh, you are a writer? Have you written anything I may have read?”

Few people overtly question if you are a good accountant or a good HR representative, but oftentimes, they have no problem immediately judging if you are a “good” or “real” writer or not if you have achieved success in terms they can immediately quantify. They seek proof of your writing’s validation in measures they can understand: fame and money.

When you venture out on your own, as writers and other creative professionals do, you are making an active decision to CREATE risk in your life—where you not only have something to gain, but something to lose.

Too often, we think of the “risk” of being a creative professional as that moment where you say, “Go for it!” and jump off a cliff. The image is exhilarating, and for a moment, you feel free and empowered. “For a moment” is the key phrase here.

What I have learned in my own creative ventures and risk-taking, is that I could care less about that moment. That moment is a postcard, an illusion sold to a tourist, where a marketer is dumbing down a complex scenario to a simple emotion they can sell.

“Go for it!” “If you can dream it you can do it!” These are easy things to “Like” on Facebook. Imagine the scenario where a friend says, “I am selling my house to travel the world and become a writer,” and you click a simple “Like” button, supporting their decision, while taking on none of the risk. “Empowerment” is what people encourage you to feel about risk, and while it may be a byproduct of actions that require risk, the initial buzz of it quickly wears off. Those “Likes” feel amazing, but they don’t pay the rent, and can fuel you through only so many sleepless nights.

What lasts is what you find on the other side of risk—the side after you jump, where you land on the rocky ground, sprain your ankle, skin your knee, knock a tooth out, and break your arm. Where you then dust yourself off, look out at the long desert in front of you, and begin to march into the unknown. It is a place where the friends and family giving mild encouragement are safely in the distance, wishing you well, but daring not to step into true danger that comes with such a journey. Don’t get me wrong: they “support” you, much as a bumper sticker supports any social cause. But they don’t want to be out in the middle of a hot desert with no water, no direction home (hat tip to Bob Dylan), and a dust storm forming on the horizon.

You, on the other hand, actually DO want to be out there, because when risk ceases being an easy encouragement of “go for it,” a simple slogan of “Just Do It,” or a simple inspiration of a cat hanging on a ledge (“hang in there!”), very good things can happen. It is in this place where you develop the capacity and skills to truly create something original, and where you push yourself beyond limits you assumed were unbreakable laws of the universe. Suddenly, you will be accountable and open to the real risk of failure—and the judgment of strangers.

That blog comment I referenced above, the one that called me a “dolt?” Oh, it went on, and it got worse:

“You and your wife are the most self-centered, crazy people I’ve run across. I hope your child enjoys the fact that both his parents are helping raise him when the entire family is destitute because his mom gave up a great job that anyone in the country would give a right arm to have amidst the worst recession since 1930 . . . When you have a small child you take the safe route.”

Yes, part of me felt a sting when reading this. I really didn’t have a clear sense whether or not my little company would work, whether or not I could earn ANY revenue, let alone enough to support my family, whether or not I had the skills to be an entrepreneur and create something on my own. I was creating a lot of vulnerabilities and this stranger had not only shoved a knife in my most sensitive place, but he had twisted it.

Even though it hurt a bit, this line really pissed me off: “You take the safe route.”

I had come to a place in my life where I realized what was sold to me as “the safe route” in terms of a career, wasn’t actually all that safe. We can easily be comforted by a job title, a pension, a benefits package, paid holidays, but that could also end very suddenly. Companies create a lot of messaging around employees being “family,” but then they institute lay-offs to make quarterly finance numbers work.

Part of me felt that this commenter who encouraged me to “take the safe route” could also be justifying his own decision to suffer through a job that he wasn’t satisfied with. When a stranger yells at you so quickly and so passionately, it seems obvious that I must have touched off something deep inside him that had been boiling for a while. Why else would he care so much about me starting a business and claim that NO ONE should start a business in a recession, or when starting a family. My guess is that I somehow touched a nerve of an opportunity that this person has let slide?

And perhaps because misery loves company, he was trying to make himself feel better by encouraging me to suffer alongside him—to take a job purely for the money, and the instant I have a child, make no decisions that could lead to professional or personal satisfaction.

The truth is, I already tried that route. I spent a decade at a big multinational media company, and by the end, my title was “Director of Content Strategy & Development.” It was an awesome job, and I loved the folks I work with. But do you know how easy it is for one executive within a corporation to decide they don’t really need a Director of Content Strategy & Development?

Pretty easy.

For years, my manager counted how many lay-offs we had “survived.” In the first six months of being at that job, in fact, our department was cut in less than half. Every night when I went to sleep I was filled with fear that one day, I too would be told to stop showing up to the job I enjoyed.

Living with this fear takes a toll emotionally, professionally, and personally. Every tidbit of gossip at the office suddenly seems life-threatening. You find yourself guessing which projects will please executives you never met, and wondering which will tick them off. You stop speaking up in big meetings because you hear stories of what happened to the guy who did. You begin to see professional risk as ONLY an action where you have something to lose. You begin to measure professional value by “not getting laid off,” and by receiving your three percent raise each year.

Everywhere I looked, I saw people working jobs they weren’t satisfied with, and using the justification that it created a solid financial foundation for their families. I was constantly being told I was “lucky to have a job,” not because I was a poor worker, but because everyone was clinging to this narrative that ANYONE was lucky to have a job.

I was 36 years old when I started my company. When I left my corporate job. When my wife left her tenured job as a teacher. When we had our son. When the recession was at it’s lowest depth and every message in the media was touting how much the bottom had dropped out. This is a time where every indicator around us was yelling: “CREATE SAFETY.”

But I became obsessed with how you create a bridge from one version of your life to the next. How you can take proactive action to create the life you want, instead of merely reacting to the world around you—the one laced with messages of fear.

In 1990, one of my favorite bands—U2—took a huge creative risk and reinvented themselves. Bono describes the process this way in a documentary called “From the Sky Down”:

“You have to reject one expression of the band first, before you get to the next expression. And in between you have nothing. You have to risk it all.”

That phrase—“in between, you have nothing”—is the part of the story that we gloss over when telling stories of our heroes, or when we look to success stories used to model our own potential actions. But it’s the part of the story where the power lies, and writers inherently know this.

Writers are people who, by definition, do not take the safe route. It makes little sense to decide to write and publish a book. It is, in fact, totally insane. Let me count the ways:

• Social risk (of putting oneself “out there” in sharing something so personal, so publicly—and risking embarrassment or shame)
• Financial risk (whether you measure this in terms of money or time, it’s going to cost you big time)
• Emotional risk (of inviting in 24/7 anxiety amid thousands of decisions in the writing, publishing, and marketing processes)
• Professional risk (of pushing boundaries instead of just doing what is expected or what you have been told to do)
• Personal risk (of your identity with family, friends, and community—writing a book is raising your voice. It’s standing on a soapbox. It’s saying, “my authority will be written down, duplicated, and distributed for all to see!”)

Of course, that is why I admire writers so much, why they are infinitely inspiring to me. They take risks for exactly the right reasons. For the chance to create something magical that truly shapes someone’s life in a meaningful way.

So what do writers know that allows them to write despite the risk involved? Why create? Why start a new business? Why invite risk into your life when the world around you is encouraging you to “play it safe”?

I think that deep down, writers understand that there is a story in their head—SOMETHING—that needs to be expressed, explored, written down, and perhaps even . . . shared. This is an almost primal process, something that happens before a writer considers getting an agent, a publisher, or onto the bestseller lists. They can’t not write, regardless of consequences.

The act of writing, sharing one’s work, and engaging with conversations around it, is a spectrum of risk that writers work across. There is not a single “moment of risk” in choosing to write, but it is a process that you constantly work through. For instance, when an author comes to me when they are in the midst of launching a book, they sometimes ask for “best practices” and a structured “marketing plan.” While there can be value in these things, what they are really asking for is a way of mitigating risk.

Just as no two books are alike, no two authors are alike, and no two relationships with an author and a reader are alike. What authors need to develop are not ways of reducing risk, but instead ways of developing the capability to maneuver through it. For instance, you don’t drive only on “safe” roads, you instead drive anywhere you need to go, and develop an almost subconscious ability to identity and react to risky situations.

What you gain from the process of moving past these situations is FAR greater than the risk inherent in each of them. If your book tanks, you have still learned how to write a book, publish a book, partner with others (publishers, booksellers, editors, etc.), and now have a CAPACITY that is infinite in it’s potential.

Be aware that people might not like it when you do the risky thing. When I left the corporate world to start my company, some people didn’t believe I was telling the truth. There were friends and colleagues who literally thought that my saying “I am starting my own business,” meant that I was trying to save face while looking for another job. I would tell them about my plans, and they would say, “You’ll find something soon.” For months and months, people still referred to me by my old job title because that was easier than trying to describe a fledgling business.

To my surprise, I began to discover that many people who are mid-career prefer this conversation: “OMG, my boss is such a jerk . . . ” than this one: “I’m so excited about this new little project I am working on . . . ” One is reactive, the other proactive. And there is safety in being reactive, just as there is safety in being a critic instead of the person who creates the work being criticized. Both require skill and insight, but the instigator is the one who truly puts themselves on the line.

Likewise, letting people know that you are writing a book can feel as though you are providing them with ammunition to use against you. Every casual meeting can be filled with a question of, “So how is the book going?” to which you may mumble a sheepish answer, because you just threw out chapter two, you just realized it’s going to take you three years to finish, you know that in the last week you only wrote one good sentence. This is akin to the unending pressure one feels when they announce their engagement :

You: “I just got engaged!”
Your aunt: “So, when is the wedding?”

You: “We got married today!”
Your aunt: “So, when can we expect a little one?”

You: “Our son was born today!”
Your aunt: “So, when will he have a little brother or sister?”

The dark secret is that sometimes, your friends, family and colleagues don’t WANT you to succeed. Success is a mirror. Those around you can be patient for it long enough to say “congratulations!” but much beyond that can instantly be translated to gloating in their minds. Why? Because it forces the other person to reflect on their own ability to take a risk and achieve one of their dreams.

For instance, when one person says, “After having 3 kids and feeling overwhelmed 24/7, I wrote a novel, found an agent, and landed a publisher!” it means that they worked through an incredible challenge that you might not have faced. Perhaps your excuse of “Oh, sure, I WANT to get back into writing, but you know, how does one do that with three kids,” is not longer a conclusion, but a choice. And hearing that someone has succeeded in this challenge may surface all sorts of internal insecurities and anxieties in a friend, family member or colleague.

The possibility of you succeeding would call into question the narratives that they live by. Perhaps they didn’t follow a creative dream because it seemed risky, but since you are doing it, it makes them realize that it wasn’t the THING that was risky; it was that they didn’t want to commit to the uncomfortable PROCESS and work past it.

I’m sure that you have barriers in your life that are preventing you from pushing forward into the wilderness of risk. That may involve responsibility to kids, a serious illness you are battling, a job that seems to take up every waking hour of your day, finances that never seem to add up, fear of judgment or emotional/psychological fear from trauma you have suffered with for years, where anxiety is your normal state of being.

I get it. These things are real.

The point is not to make these challenges go away, to wait until you are in perfect health or for your kids to be grown, or to win the lottery. It’s like that old saying: the brave do not lack fear, they experience fear and proceed anyway.

The risk you take in writing is not a moment of jumping off that cliff. It is the simple step you take once you land on the ground. And that first pathetic limping step, where you are shivering and confused, where every direction feels wrong—THAT is the moment that matters most. The choice to move forward anyway, through the challenges, even if you are convinced that finding only five minutes of time to write per day could never add up to your dreams. I can’t promise you that it will. But I know that if you don’t start, if you never embrace the risk, if you never start needling at the barriers to find a weakness in them, you will never move forward.

Was that blog commenter right? Was I a “dolt” for taking these actions? For welcoming risk into the life of my family? Well, at four-years into this venture, all I can say is that my wife, son, and I spend loads of time together every single day, and my business has been doing well, and that we are happy.

Maybe I am a dolt. And if so, I absolutely don’t mind!

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