We live our lives through conversation, not writing. To improve your writing skills, try writing the way you speak. We often get bogged down by the "right" way to say something in writing—something we rarely worry about when talking. By saying out loud what you want to convey, you can get much closer to a clearer, more natural statement. So, the next time you're stuck, ask yourself, "What am I really trying to say?" Then, say it out loud.

Very often when I am editing a text for another author, I have occasion to ask about a certain passage, or even about the entire work. What I am looking for is a better understanding of their intent and meaning and objective, so that I can help them bring that out more clearly in the text. Obviously, if the text were already doing that, there would be no need to make the call.

During the course of the conversation, I will usually ask them to kind of back away from the writing they have given me, and simply explain to me what it is they are trying to say. Almost every time, the very next thing I hear is a surprisingly clear and lucid summary of their intended message. They are clear about what they want to say, even though their text is not. I cannot tell you how many times I have found myself saying, “Well, why don’t you just say that?” Meaning, what’s wrong with taking what just came out of their mouths, and using that as the core text for the passage/work in question? I am always struck, and I think many times they are, by the ease with which they were able to say out loud something they were struggling to say as clearly in print.

There is an old joke about a man and a plumber, which ends with the punchline “Knowing where to knock: $495.” I am pretty good at maneuvering an author into giving me the right answer. That said, it is still remarkable how often an author comes up with a more or less perfect formulation of their message, when prompted in conversation.

I suspect that this is accounted for by the fact that we live our lives in conversation, not in writing. What this means is that from the moment we learn to talk, we are practicing the formulation of thought impulses into streams of spoken language. That’s a lot of practice.

Consider how we learn to write. For that matter, consider that it is possible to spend a lifetime communicating in spoken language, and never learn to write. We are taught to write years after we learn to speak, and we are taught using spoken language. Once we learn, we get more or fewer chances to practice, depending on our life circumstances. But inevitably, unless we lead very unusual lives, we get far fewer chances to practice writing than speaking.

And then there are the rules of writing. When you are in conversation, no one is checking to make sure your punctuation or spelling or grammar or noun phrases or compound complex sentences are constructed properly. But when you write, it is a very different story. All of those rules (You want rules? We got rules! the Chicago Manual of Style—17th Edition—runs to 1,144 pages and weighs almost four pounds.) hundreds if not thousands of ways how your work can be wrong. We internalize many of these rules along the way, else we could not construct meaningful sentences, but very few of us can articulate more than a handful. Yet we know they are out there, and we get all caught up in worrying about the correct way of saying something in writing—something we rarely do when speaking. So we have what is, relatively speaking, an unpracticed medium with myriad rules we know are there but of which we do not have mastery. No wonder people struggle to get their message into written form.

There are a couple of ways to ease this struggle and become less hung up when it comes to writing. The first is, of course, to simply write more. Get more practice. Invest in the study of writing. Read different good writers and watch, absorb, the rhythms of good writing. For me the main challenge is to learn to draft first, edit later. Suspend the rules of “good” writing when drafting, and focus instead on just generating text. Get it out on paper without any regard for whether it is “good” or not—that will be far easier to determine once it is in print. Say things multiple times. Curse. Don’t think about how to write it; think about how you would say it and then write that down.

Which is in fact the second way of getting closer to a clearer statement in a written draft. We each of us carry around several thousand years worth of evolution of our language-generating function. We know it works. So the thing to do is ask yourself “what am I trying to say here?”, and then get yourself to say it out loud. You could just let it form itself in your head, but there is a kind of crystallization function that happens when you speak something out loud, which simultaneously creates correct speech and makes immediately obvious which thoughts in your head are not as clear as you thought. Even if you have to break it up into smaller chunks—find a way to say out loud what you are trying to say, and then write that down verbatim. Then don’t worry about it. Just use it. Put it into your draft, and edit it later or have someone else (that would be me) edit it for you.

The point is that we forget how much easier it is for us to articulate things in speech rather than trying to “write down our thoughts.” We can take advantage of thousands of years of evolution and practice, and let our relative fluency with spoken language find the right words for us.