The Progression of a Writing Life Part 2: Risk

As a writer progresses in her craft, she may sometimes wonder how her particular path will look. In this four-part series, Charity Singleton Craig envisions a possible progression of a writing life through the lens of a snowboarder. In today’s installment, she considers the role of risk.


Writing in the Half Pipe

For months after watching the snowboarding competition in the 2014 Winter Olympics, I couldn’t stop thinking about the similarities between the writing life and these extreme sports. For most of us, comparing our writing lives to winning Olympic gold medals creates a false sense of what qualifies as success. Athletes in the limelight, like snowboarder Shaun White, inspire millions of children and adults to take up the sport. Most of these newbies, however, never go on to compete in the Olympics or land product endorsements like their heroes. They can still have rewarding amateur or professional careers, though.

That’s why sports journalist Esther Hershkovits believes American Sage Kotsenburg’s gold medal in slopestyle snowboarding did more for the sport than if mega-star Shaun White had won in the Sochi Games. In her February 2014 PaperMag article, Hershkovits discussed the high-stakes tricks of a few elite performers that draw most of the attention and sponsorship dollars, but overshadow the hard work and artistry of the snowboarding community as a whole.

“The majority of professional snowboarders do not compete in the X Games or in the Olympics but rather take their skills from terrain parks and apply them to urban settings or the back country,” Hershkovits writes.

This is the natural progression from play to risk that athletes—and writers—must make. We all have to work hard, take risks, commit to our craft. Some of us will achieve breakaway success, even in the early days of a career. White scored his first corporate sponsor at age 7. But the majority of us will never rise that quickly, or that far, and still, we will see rewards for our risk. We may even find “success,” if we are open to evolving definitions.

Though I now make my living from words, my early days in the writing life looked nothing like a professional writing career. While I committed a great deal of time to writing, I spent most of my days doing other work. The writing I did was rarely compensated, and to this day, about half of my published writing is done for free or with very little payoff—monetary or otherwise.

Does that mean I’m still just learning my jumps, still practicing in a shallow pipe? Maybe. I think there are a lot of us writers wearing extra padding and playing it safe as we grow more confident in our skills and plan ahead for bigger moves, greater speeds, and deeper pipes. On the other hand, maybe the greater risk, the risks millions of writers take every day, is to commit in a big way to my craft even if it never pays off in the typical ways, like a big advance or a best seller list recognition. Taking these risks, doing the writing I want to do even if there’s not a large commercial audience, is success in its own right, even if it don’t produce the same results I dreamed about when I was younger.

In other words, I can look around at the few writers who have made it big, resenting their tricks and envying their endorsements. Or, I can use their achievements as a motivator to keep improving my style, submitting my work, and finding my own definition of success.

Make the Most of It

Taking risks in the early days of writing felt exhilarating.

When I was just out of college and hoping for a career as a freelance writer, I pitched ideas and sent query letters to national magazines as often as local newsletters. In my naivete, I didn’t realize how hard it was to land a spot in some of those big name publications. I had little to lose. I didn’t have a reputation; I wasn’t trying to support myself or a family.

The myth of overnight success was a lusty muse to this young writer.

Keep Growing

After a few too many rejections, however, my exhilaration waned. For long stretches, I didn’t write anything at all. The fun was gone. The risks weren’t paying off. Even now, I could use a little more of that moxie. Too often I take myself and my writing so seriously. When a friend recently suggested I submit an article to a large prestigious magazine, I hedged. Too risky.

To keep growing, though, I am going to have to take some risks, and it’s not a risk if there isn’t the real possibility I might fall flat on my back.

Read The Progression of a Writing Life Part 1: Play

Photo by Raul Lieberwirth. Creative Commons license via Flickr. Post by Charity Singleton Craig.


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  1. Laurie Flanigan says

    Thank you for this, Charity. I really enjoyed reading it. It feels candid, genuine, encouraging, and helpful. I hope I get to read the results of some of your risks.:)

      • Laurie Flanigan says

        It seems like all of life’s a risk, Charity. It’s risky getting out of bed in the morning, and it’s risky staying there longer than I should. 😉 I do write, but saying, “Yes; I am a writer.” feels risky to me. Every time I post a poem here, or even to my own Facebook feed, it feels like risk. Poetry is such a misunderstood form, and all writing and self expression seems to take a certain kind of brave and a lot of falling on your face. :)

        • says

          Laurie – Thank you for this thoughtful response. You are so right about risk. I guess the question we ultimately arrive at is how much risk can I tolerate? When I set up an IRA recently, the financial planner offered me a risk scale. It would be interesting to apply a similar concept to the types of risks involved in the writing and living I do. It might help me realize that I am open to being a bit riskier with my work. Or maybe not so much. I think you are right that poetry is inherently risky, that may be why certain civilizations and governments over time have tried to quiet their poets. Thanks so much for engaging with me here.

  2. says

    Large and prestigious are overrated.

    But this, this place right here where you encourage as a friend, rather than an elite, untouchable, this is the good stuff. At least for me. :-)


    • says

      Thanks, Darlene! I think the writers who make it big have a valid story of their own to tell. And to be honest, no one makes it big who doesn’t first try. I just know that for me, I have to learn how to take risks and measure success in ways that also move me forward and don’t cause me to get stuck in disappointment.

      Thanks for your encouragement. I think Tweetspeak offers the best kind of place for this mutual encouragement among writers.

    • says

      Sandra – I am wondering if there weren’t as many (or at least as many obvious) places to write for free back then, because I feel the same way. Like I missed an opportunity.

      Oh well. We are here now. And we are able to weigh the risks of all kinds of writing possibilities and opportunities.

      Thanks for adding your perspective here.

  3. says

    I know your heart and your words from the invaluable writing life workshop I participated in with you at the helm. You have made your mark on me as a wise encouragers. Just as you do here in this space for writers and poets and fun-lovers.

    We need new measuring sticks for success.
    We need new paradigms for what is real and shiny and important.

    You are a Pulitzer Prize winner in my book. And for me that is to say, you have reached the mark of touching another soul. Where you go from there, may it be gravy. :)

    What more could we need or want as writers.

    I am so looking forward to your book with Ann. And to writing over at your blog. What a privilege that invitation is and was :)

    • says

      How lovely, Elizabeth. Thanks for your encouragement.

      And I love your thoughts about new measuring sticks and new paradigms for success. I think technology is rapidly offering us a bunch of new ones. Whether or not we adopt them might be another thing, huh?

      Your point about reaching another soul is definitely a mark of success in my book, too. I wonder, though, if it’s possible to have multiple goals, and therefore multiple benchmarks of success, for the same project or for the same career. For instance, if I want to reach people AND make money, what will success look like? Or, if I want to reach LOTS of people and stay true to my own artistry (regardless of market pull), what will success look like?

      I think have these variegated success models makes measuring success more difficult. But they also make our work and careers more interesting.

      Thanks so much for your comment. You have led me down a new path to explore.

    • says

      Thanks for your encouragement, Jody.

      Yes, Ann Kroeker and I have written a book about the writing life that is currently in editing and production with T.S. Poetry Press. It should be released later this year. We are really excited!

  4. says

    It’s the riskiness that gets me. I do most of my writing for free, and what I like about that is it relieves the pressure of risk. I don’t have to put my stuff out there for approval/disapproval. But now, I think I need to go there. And I’m resisting it, bigtime. Part of that is this dang long recovery, but part of it is just plain fear of the unknown and looking the fool. Not good enough reasons not to try, right?

    • says

      Diana – I hear you about the pressure. I think that’s why I do a good amount of free writing, too. You’ve really nailed it when you talk about the fear of looking the fool. I feel that every time I submit something. I think that’s part of the writing life, though. Learning how to quiet, if not ignore, those voices.

  5. says

    I’m really looking forward to reading your’s and Ann’s book, Charity.

    The myth of overnight success is fascinating to me. My dad once told me he heard a musician say “after 18 years of hard work I became an overnight success” and I never forgot that. It’s pretty rare to truly have overnight success, and to those who have it I wonder if they ever wish they’d have come up through the ranks. The ranks have a lot to offer, don’t you think?

    • says

      Donna – I love the way you make “the ranks” a real thing, something with value, and a place to grow. I think “the ranks” grounds us in a way that overnight success may not. Of course, I’ve never had overnight success, so I can’t be certain. I love Chris Guillebeau’s manifesto: 279 Days to Overnight Success (×5/files/2009/04/279days.pdf). It offers the same perspective as the musician your dad heard: even what may look like overnight success is likely the result of lots of hard work. Thanks!

      • says

        I’m looking forward to reading that one! I bet my dad would like it- I’ll pass him the link (I think it’s very cool that he is learning how to use gmail at the age of 82… speaking of risk).

        I think about the American Idol movement a lot and wonder if it isn’t more debilitating to the onlookers with dreams and real talent than for the ones who get their break. They work VERY hard, and if they want to stay in the floodlights they have to keep it up all the time.


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