In the first two posts of my series, Your Write Turn, I tried to convince you that you can pursue any number of new career choices after the age of 50—including becoming a writer—and I gave you a personal inventory to run through in determining what you bring by way of resources and skills to a new career as an author. Now, let’s talk about that 600-pound baby elephant stomping around your newly decorated writer’s garret.

Self-doubt. Imposter syndrome. That persistently inconvenient voice in your head that keeps screaming, “I suck! I’m not good enough! Everybody writes better than I do!”

Having self-doubt in high school is what beginning a writing career feels likeRegardless, of age, jumping into writing is very much like going back to high school. Just like freshman year, you don’t know where you fit, whether you’re cool or not, or if anyone will ask you to the homecoming dance. Those same basic insecurities come rushing back, repackaged in older labels. The good news is you won’t get wedgies or stuffed into lockers—unless you do it to yourself. Which would be another problem all together.

These old feelings of inadequacy will likely come as a shock to you.  You’ve spent the last thirty or forty years becoming Successful at Doing Things—parenting, managing, marketing, surviving five or six decades. You probably convinced yourself that you were well past this kind of teenage angst. Aren’t I past that stuff, like getting random pimples? Well, you’re not. Full confession: I still get nightmares that I’ve slept through a final exam or haven’t gone to any of the lectures all semester. At 60, this seems somewhat unfair to me. But there you are.

Memoirist Carrie Classon took up writing at age 50 and really went the whole hog. She enrolled in a creative writing course in a different state and moved into a converted garage. She describes her initial experience, “My fellow classmates were all half my age and twice as smart.” She recounts being asked by her professor in an early class, “Haven’t you always wanted to write?” Her honest answer was, “No. Not at all.” She was the only one in her class to admit that. (Her first book, a memoir entitled Blue Yarn, came out in 2019.)

And here’s the real shocker. It doesn’t matter how successful you are as a writer. This self-distrust never goes away. A year or two ago, I read an interview with author Hilary Mantel. I mean, this lady has crushed it. She won back-to-back Booker awards for her novels, Wolf Hall and Bring Up the Bodies. It takes a heap of talent to turn Thomas Cromwell—the heretofore uninteresting Cromwell—into a literary pop icon. (Okay, she was helped a little by perennial favorites Henry VIII and Anne Boleyn being part the story, too.) But in this interview, Ms. Mantel confessed that the reason she was taking so long to finish the final volume of her Thomas Cromwell trilogy, The Mirror and the Light, is that she was so terribly afraid of disappointing readers after the great success of the first two volumes in this trilogy. That is classic writerly self-doubt… albeit buffered by a big advance from her publisher. Or perhaps aggravated by that big advance?

So not only do we have to worry about Imposter Syndrome when we’re not selling any books, we still have to worry even if we’re selling gazillions of books and winning Booker prizes.

One of my personal writing heroes, Ernest Hemingway, suffered his entire life from crushing self-doubt. The last novel Papa H published in his lifetime, The Old Man and the Sea, was serialized in Life magazine ten years before his death. When you couple this self-doubt with the crippling depression that ran throughout the Hemingway family, it’s no surprise that his life ended in suicide.

Whoa, that was a downer.

Enough of the cautionary tales. So, how do we get over the hump of self-doubt as we launch on a new career as a writer? The deceptively simple and completely ungratifying answer is… write. I suppose I should elaborate a little, yes?

With three novels out, I’ve Learned Some Stuff along the way about self-doubt and Imposter Syndrome. Let me distill my own sleepless nights and tortured-artist hand-wringing into a handy list of Do’s and Don’ts.

Things you should definitely DO:

– DO set yourself a realistic and achievable daily or weekly word count. I like daily counts because they keep me sitting in the chair five days a week. Since writing is a job—my job—I work Monday through Friday and take off weekends to be a regular human being. Make sure to keep some time for your Significant Other, family, and friends. After all, you need somebody around to bore with tales of your writing struggles.

Reward yourself after reaching a writing goal– DO find ways large and small to reward yourself. This means getting in touch with your inner child. It’s like when your parents said, “After you clean your room, we’ll go for ice cream!” Try something like, “When I’ve written my daily word count, we’ll go for martinis!” or whatever your favorite flavor of Adult Ice Cream might be. You’re never too old for this kind of positive reinforcement. I highly recommend it. It’s also a good way to pay some attention to your long-neglected spouse, who could likely use a few cocktails, too.

– DO think hard about your own level of self-discipline. You can’t blithely assume every day will produce an easy 1,000 words. On some days, the words will flow out of you like water. And on other days, that 1,000 words will feel like passing a thousand kidney stones. The good news is most days are somewhere in between. Be mindful of the hard days and push yourself through them. Remembering those halcyon days when you wrote 3,500 words by lunchtime can help—but don’t let the rarity of those days discourage you. They are precious but few and far between. Also, those aforementioned martinis might help.

– DO find your own yardsticks for measuring incremental success. For example, I use Scrivener software to write the first few drafts of my books. Scrivener comes with a built-in word count meter that you can hide or keep up in the corner of your working screen. I’m a Hider—displaying my word count constantly would make me crazy. I love the feature in the word count meter that shows your progress through the day on a bar graph that turns from red to orange to yellow to green as you approach your daily count. Some people like to print out their pages or chapters as they complete them. That’s okay, too. There is something primally gratifying about seeing the stack of paper thicken and feeling the heft grow. Other writers use a time limit rather than a word count. This may be a good measure of your writing discipline if you still maintain an eight or ten-hour a day job. Often, your writing has to be scheduled for 90 minutes before the rest of the family gets up or two hours after they’re all in bed. In these circumstances, using a time limit keeps you from staying up till 4 AM diving down some narrative rabbit hole. Also, it’s good for maintaining the sanity and goodwill of those around you.

You probably won't write like James Joyce– DO organize to write. This is a little controversial—the Writing Tribe is firmly divided into Planners and Pantsers, as in fly-by-the-seat-of-your-pantsers who stick a blank piece of paper in the typewriter and let the creative forces them wherever they lead. I know that James Joyce and Virginia Woolf became everlasting favorites with their stream-of-consciousness writing. But 99.9% of us are not Joyce or Woolf. And he was a drunk who died at 58, whereas she filled her pockets with rocks and drowned herself at 59.

Especially when entering the writing game after many years of a structured work life, organizing to write is immensely helpful. I rely on the (virtual) cork board in Scrivener, using (virtual) note cards to outline my books down to the scene level. This is not elaborate outlining. Each note card contains the setting, the characters involved, and the one or two objectives I have to achieve in that scene. And then I just write down through the (virtual) stack of notecards. This gives me just enough detail to keep the character arcs and plot lines coherent, enough digestible-sized bites to build my daily word count, and the security of knowing what I have to do next. I’ve found is the best vaccine available against writer’s block. By the way, I get plenty of “pantsing” within each scene—I’m often astonished at where a scene will take me—but at least I always have a place to start and end. You can organize to write any way that works for you—fancy software, yellow legal pads, (I use those in my earliest noodlings for a story), or the back of cocktail napkins. Whatever works for you as a system.

– DO get that first draft done. Get through it, push through it, muscle through it. Give yourself permission to write badly and get it done. Great novels were not written, they were re-written. Nobody writes like Hemingway, including Hemingway—he re-wrote like Hemingway. Although nobody should ever see that first draft but you, it allows you to say out loud and in public, “I’ve finished the first draft of my manuscript.” There is no better cure for Imposter Syndrome than 120,000 words on paper.

Now here are a few things you should definitely NOT DO:

– DON’T write whenever the spirit moves you or you feel the muse calling or the planets properly align. That is a formula for never finishing anything. I have met a lot of people at writer conferences who say they’ve been working on their first book for eight or ten or fifteen years. The vast majority of these people may be greatly enjoying The Writer’s Lifestyle, but they aren’t and never will be professional writers. As a rule of thumb, Stephen King claims that no first draft should take longer than one season to write, about three months. Of course, he’s Stephen King and he’s written ten pages a day, every single day, since Carrie in the early ’70s. But never lose sight of the truth that writing as your new career requires a disciplined process. There is no other way. On the other hand, if all you’re really after is being able to call yourself a writer at cocktail parties, have at it. I’m not talking to you anyway. But hey, it’s your journey.

– DON’T rely exclusively on your family and closest friends to tell you how good a writer you are. This may come in handy in the very earliest days, when you’re making the decision to take the leap into a writing career. But as a long-term system of motivation or—gasp!—editorial review, Here There Be Dragons. The only way to keep Imposter Syndrome at bay is to produce pages and pages of good, solid, interesting writing. All that said, some writers are blessed/cursed with a family more than willing to give them honest criticism. I suspect that is rare, although I’m lucky enough to have one of those families. It may be connected to being Irish—it seems we’re genetically programmed to find great joy in Lopping the Tall Poppies. (I’ll talk more about writing as a family business in a later “Your Write Turn” blog post.)

– Finally and most importantly, DON’T get discouraged by a few hard writing days or a few missed word counts or that awful little voice in the back of your head that speaks of nothing but inadequacy. Go easy on yourself for your failures–we’re all fallible and sometimes lazy and frequently procrastinate. You have a story to tell, a story that has never been told in exactly the way you can tell it.

You can find other installments of my Your Write Turn blog posts HERE.

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