It's important for new writers to ask the pros about the mistakes they've made; successful, well-published writer and WD contributing editor Jeff Somers reveals why.
“Nowadays most people die of a sort of creeping common sense, and discover when it is too late that the only things one never regrets are one's mistakes.” — Oscar Wilde
At the first job I ever had, one of my duties was to keyboard articles destined for publication that were delivered typewritten on hardcopy. This was tedious work, and at some point I discovered a primitive scanner with optical character recognition (OCR) capabilities that produced text that was about 10 percent accurate and 90 percent gibberish, but at least it saved me that 10 percent of typing. And then, inevitably, I somehow managed to publish an OCRed article in its raw form ... which means it was 90 percent gibberish.
The point being: Mistakes were made.
Mistakes are part of life, and we all make ‛em, including writers—even successful, well-published writers. Even the successful, well-published writers who show up at writing conferences to be on panels or give presentations. Of course, speaking as one of those writers (we’re handsome, too, as a rule), it’s sometimes hard to admit to your mistakes, or you make a conscious choice not to mention them. We’re obviously cultivating the image of the wise Jedi to your padawan, and admitting to embarrassing missteps kind of tarnishes that image.
Which is why you should ask every author you meet about the mistakes they’ve made.
To Err is Human
A lot of self-professed ‛gurus’ like to pretend they haven’t made a single error in their relentless pursuit of success—it’s part of their brand, what they’re selling to you. But of course, they have made mistakes; we all have. Asking a writer about their bad decisions and blind spots will instantly tell you a number of important things, like:
Whether They Are Worth Your Time. If an author doesn’t have any examples of mistakes to offer you, they don’t have anything to teach you, either. Wisdom doesn’t come from success. Success without mistakes is usually not reproducible, because it just sort of happens, and as a result the writer probably can’t explain to you why a strategy for selling a novel or an approach to getting freelance work was successful in the first place. Failure and mistakes, on the other hand, are the greatest teachers around. Worse, if the author is lying about not making mistakes, well, you know something pretty important about them right there.
Schadenfreude Builds Confidence. We all have our doubts from time to time—doubts about our talent, our business smarts, our fashion sense. As writers, it’s easy to imagine that everyone else is doing much better at this than you are—they publish more, get paid more, and get better reviews. When a successful writer stands on a stage confidently answering questions, it can make you feel like you’re an impostor.
Which makes hearing about their mistakes so powerful. It’s not about cutting anyone down to size. It’s about reminding yourself that your mistakes aren’t career-ending or insurmountable. Hearing that a writer you admire and whose work you enjoy has screwed up can be a huge confidence boost. It reminds you that we’re all human, and we’re trying to figure things out together.
Context Matters. If all you ever hear from a writer is what worked for them, you’re missing at least half the information, probably more. Why did that strategy work? What else have they tried? Did other approaches almost work, or work but to a lesser degree? Hearing about their mistakes and failures contextualizes their success for you, making the information gleaned even more valuable. It also firms up what, exactly, they mean by ‛success’—a crucial metric that informs your own reaction to their advice.
The other context you get from hearing about mistakes is simple: Hearing what someone considers to be a mistake can offer real insight to the rest of their opinions.
So, next time you’re in the audience and some famous (or not-so-famous) writer is offering you career advice, using their stellar resume of publication credits and fat freelance or royalty checks as proof of the value of their ideas, ask them about their failures and their mistakes. The response you get might be more inspiring than their intended advice.
 I am so very, very old.
 You think *you’re* lazy, but I’m so heroically lazy I can’t even come up with a decent footnote here.
 Then again, so was most of the stuff I said at my job interview and yet they hired me anyway, so who’s really at fault here? That’s right: Capitalism.
 I wasn’t fired on the spot, though I should have been. Back then I still possessed the power to make people pity me.
 Like, say, the fact that you are somehow incapable of pronouncing the word ‛sawhorse’ correctly, producing a word that sounds something like sowhawse no matter how hard you try. If you want to make me burst into tears and run off the stage at a panel, just ask a question that requires me to use ‛sawhorse’ in a sentence.
 That’s why my brand is 50 percent day drinking and 50 percent ... night drinking.
 For example, I once tried German whisky.
 Close second: Hangovers.
 I’m an exception on that third one, as ‛vaguely disheveled’ has worked for me as an iconic look since 1995.
 Unless every answer is them making finger guns and shooting noises at you, then pausing for applause that never comes. Then you actually feel pretty good about yourself.
 Okay, it’s a little about that.
 For example, I consider any day I remember to put on pants before leaving the house to be a success. Which tells you everything you need to know about how things are going. Shut up.
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