feature image 3 great challenges of writing

I find myself with little to say sometimes. It rarely stops me, mind you, but there it is.

I’m at or near the end of what I think must constitute a chapter of life. I’m almost thirty, I am starting to find a bit more success at writing, I’ve reached the end of the first big project of my career, the one that brought me here to the Valley of the Sun. I’m looking for a place with my girlfriend, just the two of us, and my family is selling my childhood home. If this was one of those fancy long books divided into three acts or books, I might rapidly be approaching the page that says only, “End of Book I”.

It seems fitting, then, to write something on this concept of threes, specifically the three great challenges of writing.

section header card being the writer

I. Being the Writer

The first challenge, the foremost, is being the writer you need to be. Writing is a simple concept with a simple execution, where we stack symbols together to represent our thoughts. The entire process is designed to be grasped in basic form at about the age we can tie our shoes, and effectively mastered by the age we can be trusted to live independently.

In other words, it’s a thing almost anyone can do, and, consequently, a thing which is exceedingly difficult to stand out while doing. Just think how often do you see someone walking down the street and say to yourself, “Wow, that person is really good at walking!”

Every successful writer I know writes a lot and they do that for the same reason that good runners run, strong weightlifter lift often, and so on. More than just often, they push the boundaries. Writing is a direct connection to the mind of another living person and done right it can accomplish almost anything. Wonder, despair, love, hate, fear, joy, all can be conjured from nothing, and be no less real for the cause being something ephemeral or imagined.

I believe the underlying magic of the act is often overlooked. There are not many parallels to this, where something imagined is simultaneously real; we can feel empathy for characters who’ve never lived, inspiration from events that haven’t yet happened, wonder for places only dreamed. They don’t exist, nor their joys and pains, but still, their happiness or hurt is felt when we feel it for them.

To reach that point, though, you walk across a million broken sentences, and a thousand failed stories.

This sounds excessive, but I’m driving towards a key point here: In order to be a great writer, you have to love what you do, but be willing to destroy these labors of love, rebuild them in new ways . . . and maintain over and over again the discipline to do so.

I’ve met a great many people who love the idea of having written something great, but I think I’ve still got a finger or two left for the ones who want to be the person writing the books. But that’s what we do. We write the books. Writers aren’t people who have written things, and they aren’t people with “ideas”, they’re the folks who take the ideas and make them written. They are the ones who are engaged, neck-deep, make-or-break, in the visceral, active, intensity of writing. 

Once you’re not writing anymore, even if you’re successful, what you are is a retired writer. I know lots and lots of people who want to be retired writers.

failing to succeed title card

II. Failing to Succeed

From every direction this is a difficult process. It hurts to be rejected. It is a financial and personal drain on the writer’s resources to create something which is not good enough to succeed. A rejected book isn’t just a major labor lost, it is mountains not climbed, trips not taken, dates not had, and so on. That time means something in a fleeting life, and each failure compounds upon itself.

Still, the only way to improve is to keep working, and so we must embrace each failure to reach success, while we know each of those failures places us deeper in a debt we can’t rise from except by success. If we succeed, every failure becomes just a downpayment on a great investment, yet there is the very real possibility of endless failure, digging a hole deeper and deeper until it becomes the grave of every other life we might have led.

So, the only way to navigate a writing career is failing to succeed, with the very real possibility of succeeding to fail. To be a writer is to be a gravedigger with the possibility for advancement.

cotm challenges of writing 3 begs

III. Beginnings and Endings

Most writers I’ve talked to tend to say writing the beginnings or the endings are the hardest bits. I don’t understand this. Personally, I find the book in between to be the challenging part.

For me, the hard part is knowing what to start. I have ideas. More ideas than time. Should I write my own books and try to get them published? While I’m working on these huge projects, how will I pay my half of my rent? I’m thinking about starting a travel blog with sponsors, and I think I’ve got a pretty good plan, but it still involves creating a website, some content, and presentations for meetings I might not even be able to get, let alone walk away from with support. I could write some smutty romances under a pen name, throw them up on Amazon, and hope I make some passive income. I could double down on this blog, try to monetize it.

So on, and so on.

The problem is not one of options, really, it never is. Life has many flaws, and a fundamental lack of options is rarely ever one of them. It’s our own human limitations. If we want to do well, we have to choose, and then we have to put the whole of our hearts behind that choice.

Since writing is an ongoing thing, in fact, endings and begins run together, and they’re effectively indistinguishable. Reach the top of one mountain, then use that lofty vantage to pick the next, until you’re too tired of mountains to keep going.

Just don’t lose sight of the fact it’s the bits between that matter.

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4 Thoughts on “The Three Great Challenges of Writing”

  • A gravedigger with the opportunity for advancement….kind of hits it on the head doesn’t it?
    Hey…you going to be around when Chris Derrick rolls into town this fall?

  • Good piece. I never thought it would be so difficult to keep the words flowing. I studied four years to earn a creative writing diploma but ended up doubting my ability to write. The diploma is there, but the book – who knows when. ‘We must embrace each failure to reach success’. I keep tellling myself I’ll get a nice, quiet place of my own in the province and a room where I’ll spend all my time writing. And today’s excuse for not writing is that I’m working a non-writing job so I can afford that place. I still feel like I have already failed.

    • Thank you Flo!
      Some days the other parts of life take precedence over writing; that’s fine, and as it should be. After all, none of us is just one thing, and we wouldn’t really want to be, right?

      There is, though, a certain point in every goal, along every path, where we either do, or we don’t. So you write, or you don’t, excuses be damned. Personally, I find it’s a bit like running or blogging, where it’s easiest if I just stay in the habit of it, an hour here, an hour there. That said, I do long for a cabin in the woods, or a sailboat, something that can take me far away from all the things in the world which lack the good fortune of being writing.

      In any case, as long as you’re still both trying and breathing, you’ve not yet failed.


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