How Do We Know When We’re Doing Our Best Work?

My NEXT BOOK draft currently stands at 14,526 words, and I wouldn’t consider any of those words my “best work.”

Not even the 310 words I shared with you last Friday.

It’s some of my most interesting work, and I think the plot is by far my best plot, and the questions it addresses are particularly immediate and relevant to the group of people whom I envision as its ideal readers*, but it’s not my best writing.

Yet.

Which means it’s time to bring up the question that I promised I’d explore at some point: how do we know when we’re doing our best work?

I know that NEXT BOOK is not yet my best work because it doesn’t yet communicate what I want it to communicate to an audience.

That is: I know that NEXT BOOK is never going to be the story I felt inside my head, all at once, when I climbed the stairs of the Brucemore Mansion. That was kind of like… well, I’d been digging at this potential novel about Mars that wasn’t going anywhere, and my mom and I went to tour Brucemore over Christmas because they had all the decorations up, and I saw a staircase that reminded me of the staircase in this mansion that I dream about on the reg, a big old house with a bunch of secret doors and secret rooms, and I was all I want to write about a big old house with a bunch of secret doors and one of the doors leads to another world and the person who knows that has to decide whether she’s going to go.

And then I had to work out the rest of the story, because that’s really only the exposition. The decision process can’t take much more than the first third of the book, because you can’t really dangle a portal fantasy in front of your reader without eventually having your protagonist go through the portal.

So that’s what I did during the rest of the Brucemore tour, in a very general “this is what I want it to feel like” way, and I also figured out who my three main characters were and what they wanted, and then I went to the Maggie Stiefvater Portraits and Dreams seminar and started studying plot and made everything a lot more specific.

But it’s still not specific enough. With this draft, I’m putting down all the little pencil markings you do before you trace over the markings you want with ink. I’m literally writing down three different ways of describing something and telling myself I’ll pick one later.

(This probably means my actual word count, of “words that form the story and don’t just explore different ways of writing something,” is closer to 14,000.)

So… NEXT BOOK is not my best work (yet), and part of that is because I still have a lot of work left to do.

What about my freelance writing?

I still think that it all comes down to “does this communicate what it set out to communicate,” which in freelancing often includes “does this piece fulfill the client’s specs?” Did I successfully write a 1,000-word article that helps readers decide whether to sign up with Hilton Honors or Marriott Bonvoy?

When I was writing for The Billfold, I got instant feedback on whether my writing communicated what it was supposed to communicate — because if it didn’t, I got dozens of comments either asking questions about the piece or informing me of something I’d neglected to consider. I also had access to the back end analytics stuff, which meant I could see which articles were getting the most views. (This usually means you’ve got a headline that communicates what it’s supposed to communicate, i.e. “HERE’S WHY YOU SHOULD READ ME!”)

I don’t get that kind of detailed analytic information from my current freelance clients, and many sites have stopped doing comments altogether, so it’s harder to tell whether my current posts are doing what they’re supposed to do. Luckily, by this point I’ve had a lot of practice at this kind of writing. Plus, I have a new metric: am I still getting hired? Are my current clients asking me to contribute more work, and are new clients reaching out to me?

At this point, you might be asking “what about, like, beautiful prose?” I enjoy a well-turned phrase as much as the next person, but I stand by my initial assessment that it’s only beautiful if it’s understandable. Even nonliteral writing — our poets, our James Joyces, etc. — is understandable in the sense that it evokes an emotional response in the reader and by doing so communicates what it was intended to communicate.

We get Jabberwocky, even though Lewis Carroll made half the words up.

If we don’t get it, maybe it’s not for us. Maybe we’re not the ideal audience, e.g. “Pixar’s ‘Bao’ Draws Mixed Reactions From White Peeps Who Don’t Get Asian Culture.”

If nobody gets it, maybe it’s not for anybody. Maybe the writer was writing just for themselves and not for an audience. Maybe it wasn’t the writer’s best work.

One more note before I finish this up: when I teach my How to Freelance class, I ask my students to draft short posts “to spec,” and many of them use this assignment as an opportunity to show off the most beautiful and/or clever phrases they can come up with. The problem? Online writing favors clear, simple sentences. I’ve worked with clients that have required me to submit text at no higher than a seventh-grade reading level, because they want to make sure it can be understood by as many people as possible.

In this case your definition of “best work” may be different than your client’s definition — so go with theirs, and find an hour every day to write the glorious, elegant, delightful, quippy little phrases that may someday end up in your novel or memoir or poetry collection.

Make sure you write down every one that pops into your head, so you can go back and choose your favorites when you edit the draft. ❤️

*Ideal reader for NEXT BOOK: the Millennial who totally wishes they could go to a fantasy world if they had the chance, but might not actually say yes if it were offered because they’ve, like, got responsibilities. (Or, more specifically: readers between ages 23-38 who loved Narnia and Harry Potter and The Magicians and want a book where a grown adult in a time period a lot like our own gets the opportunity to travel to a magical kingdom.)

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