How Should I Get Better at Writing?

Suppose I wanted to get substantially better at writing, maybe through some kind of deliberate ultralearning project, how should I do it?

Improving when you’re at zero is quite different from improving when you’ve already invested tens of thousands of hours into your craft.

I’ve been writing for over thirteen years. I’ve written around 1500 blog posts, 5 books and probably a couple million words of text. I was trying my best for each sentence, so simply trying harder isn’t a good strategy.

Yet, at the same time, it’s not as if no improvement is possible. If there’s anything the research on deliberate practice shows is that people tend to plateau absent special effort. The volume of writing I’ve done may have even calcified some bad habits. Practice making permanent, rather than perfect.

Why I’m Interested in Mastering Writing

I think writing, like many complex, creative skills, offers a lot of learning challenges that make it interesting. Here are just a few:

• It’s not clear what makes good writing good. Great writing provokes and inspires. But it’s not always obvious what makes it different from mediocre prose. And, when your writing sucks, it’s even harder to say how to fix it.
• We don’t always agree which writing is good. Nuanced or pedantic? Descriptive or verbose? Insightful or obvious? That we sometimes disagree can make improving harder than when quality is indisputable.
• Good writing depends on more than just technical brilliance. Resonance with an audience means that writing is a vehicle for communication, and the sophistication of your writing doesn’t mean a damn if you say something other people don’t care about.

Yet, these challenges are also what make it intriguing as a learning project. When learning is just about memorizing facts and passing tests, it becomes boring. When it’s about doing something you can’t quite see how to get better at, that’s when it feels exciting.

What Approach Should I Take?

I’m not ready to pull the trigger on a new ultralearning project. However, I do think brainstorming a little at this stage might be useful. Rather than wait until I’ve made up my mind in private, I’d like to share some of my thoughts on this now.

I can think of a few approaches that might work to improve my writing:

1. Analyzing and emulating better writers.

One approach would be to pick people who I think are better writers than I am (either in terms of recognized success, or simply because I like their writing a lot), and then analyze and emulate their writing methods.

I see this approach being helpful in two ways. The first would simply be replacing ineffective habits of mine with more effective ones. If I see that someone can do something better than me, deconstructing and emulating their example will help me do it better too.

The second benefit might be expanding my toolbox. There are styles of writing I’m not strong with, that if I became more comfortable with, I might be able to apply them better to new forms of writing. Research, humor, storytelling, visual language, pacing, etc..

2. Figure out what drives quality in writing.

A qualitative analysis of other writers is interesting, but it might also be possible to do something more quantitative. Could I put an article I wrote next to someone else’s and get anonymous bystanders (or maybe Mechanical Turk) to judge which they prefer?

If you can do that, then you could also systematically vary components of the writing. Why do people like A instead of B? Is it the headline? Opening story? Readability? Do the comparison again and see what comes out of it.

This isn’t to say all writing is reducible to discrete elements, that if you just improve your headline writing by 10%, you’d win a Pulitzer. But, it would help disentangle competing hypotheses such as the importance of someone’s name, topic choice, credentials or simply hitting the right cultural zeitgeist.

Doing this kind of quantitative analysis wouldn’t be trivial, but I wonder if it’s not also something one could do in other industries/professions as well?

3. Seeking a more demanding feedback environment.

As I’ve written before, the environment can often determine the level of proficiency attained. My background as a blogger has both helped and hindered me in becoming a better writer.

For help, public blogging has meant most of my work has received some scrutiny and attention. That feedback makes it a lot easier to learn and grow.

However, I also haven’t had the same editorial scrutiny that journalists writing for major publications do, or academics who have to defend their ideas in front of experts and peers. Both of those environments cultivate different skillsets, since the feedback prevents sloppiness that would go uncorrected on a blog post.

I don’t have any plans to join a newspaper or get my PhD, however, so I would need to do something else to improve. Perhaps writing op-eds for bigger publications, hiring an editor to improve my articles or pushing myself into conversations with people much smarter than myself to force me to improve my ideas.

4. Process improvement.

It might also be useful to distinguish getting better at a skill, versus having an improved process for creating works with the skill you have. While the former involves improving your potential, the latter involves improving how your work is done in practice.

I know, from doing research on my book, for instance, that I have the capacity to include engaging stories and deep research. Yet, I don’t usually apply these skills fully for my blog articles because I don’t usually have enough time.

In this sense, improving my writing might be more about creating processes and habits that allow me to more consistently output writing near the upper part of my quality range, rather than increasing my theoretically possible writing, and then rarely reaching it in practice because of time constraints.

5. Improving writing-adjacent skills.

It might also be that writing itself isn’t my bottleneck. That I could deliver more effective writing if my ideas were better, if I had better life experiences to draw from, understood difficult subjects in more depth or cultivated authority to speak on more topics from better credentials or real-world successes.

This certainly has been a part of my already-existing strategy at improving writing. My previous learning projects helped me immensely with my writing, not by improving my writing itself but giving me something unique to talk about.

In practice, it’s often difficult to tease apart writing from the writer. Do I like Paul Graham’s essays because he’s a good writer and thinker? Or do I respect him for his entrepreneurial success and that elevates his writing in my eyes in a way I would disregard if it came from someone unproven?

This might also be something to test using Approach #2. I suspect both are important, although it’s not entirely clear what the split ought to be.

6. Exploring outside of my comfort zone.

Perhaps the key to successful writing is simply being different. Maybe writing quality is stochastic itself, and so those who take the most swings are the ones with the most home runs, and that the greater your variability as a writer, the better you’ll perform.

I’m not convinced this is a complete explanation of writing talent, but it’s also possible that my writing weaknesses are from being stuck repeating the same successful strategies of the past.

Getting out of your old habits, however, is easier said than done. Just wanting to be different isn’t usually enough. You usually also need creative constraints which force you to do something that doesn’t come automatically.

Random constraints and a random search strategy may also have the possible benefit of exploring entirely new territory in ideas and writing, which is a defect of Approach #1. If the thing that makes a great artist great is that he or she is like nobody else, then emulating successful strategies may end up repeating styles that are already overdone.

Is Analytical Improvement of Creative Skills Even Possible?

All of this deliberate improvement presupposes that this is even the right paradigm for thinking about improving creative skills. While I lean in favor of this view, others might argue that creative skills are either impossible to evaluate in terms of goodness, or that analytical approaches to mastery are doomed to fail.

One argument might be that “quality” itself in writing is totally arbitrary. Van Gogh was a brilliant painter. However his work went largely unrecognized in his lifetime. The art world around him certainly didn’t see his work as being anything special, until they changed their minds and made him one of the most famous painters of all time.

In the same way, it might be the case that what makes someone a good writer is simply irreducible to any kind of analysis. A “bad” writer, who, through chance, later becomes famous, may have all her previous work re-evaluated and elevated to the level of brilliance. If quality is determined through a fickle process of social consensus, it might be a mistake to talk about mastery in the first place.

Another argument might say that “quality” is achievable, but that it’s strictly impossible to reach this via analytic methods. This is certainly the view of some creativity researchers, who separate mundane acts of technical innovation and problem solving from “genius”-level creativity, which is genius precisely because it can’t be reduced to a formula or analysis, perhaps except after the fact.

Following this train of thought, getting better at writing is a process of inspiration and disinhibition. An emphasis on quality, particularly if it’s enforced from top-down processes of self-control, is a move in exactly the wrong direction.

I try not to rule out any hypotheses when approaching problems, but taking either of these as a starting point seem like non-starters for a project, so I’d probably set them aside for now. That may be the equivalent of the drunk looking for his lost keys under the streetlight because he can see better there, but I’m not sure there’s any way around it.

How Do You Approach Getting Better at Something You’re Already Good At?

What skill do you spend your life doing? How do you approach getting better at it, especially if you’re already pretty good? Are there any strategies and theories I’m missing above that I should consider? Share your thoughts in the comments.