Getting Good: How I’m Trying to Be a Better Writer

I have a confession to make: I’m a perfectionist.

No, not the debilitating kind of perfectionist, who can never finish a project, but the long-term kind. After publishing over a million words, I’m still convinced I can write a lot better.

I want to share what goes on behind the scenes, showing some of the experiments (failed and successful) I’ve done over the past five years to try to improve myself as a writer. My hope is that they will help you too, on your path to mastery.

Why is Getting Good So Difficult?

The problem is that just getting a lot of practice isn’t enough. K. Anders Ericsson’s research shows that, “adults perform at a level far from their maximal level even for tasks they frequently carry out.”

Repetition is enough for the basics, but it doesn’t lead to mastery. I’ve seen this in my own writing. In the beginning, simply writing every day was enough to force me to improve. But, beyond a point, more time spent writing didn’t make me better as a writer.

Ericsson explains that simply showing up to work isn’t enough. You need deliberate practice, hard and focused effort to fix weaknesses. Routine stymies growth; reorganizing the skill itself can be necessary to move past plateaus.

The research is clear: if I want to be a better writer, simply writing another thousand articles isn’t going to be enough.

Experiments in Mastery

This obsession with perfectionism has led to some interesting experiments to improve my writing. Most of them were only temporary successes, but that’s the challenge—today’s innovation becomes tomorrow’s routine.

Routine has a paradoxical relationship with mastery. On the one hand, if you aren’t consistently practicing, you won’t get growth. Showing up, every day, matters. On the other hand, if your practice is consistently the same, you also won’t get growth. Routine leads to plateaus.

During the last few years, I’ve done a lot of experiments to break my routine. Here’s a few of them:

• Freestyle Writing – This experiment involved spending an hour every day writing, without trying to create something worthy of publishing. It had some successes, including my article on holistic learning, but I eventually found it too unstructured to get meaningful ideas.
• Splitting Creative Tasks – I split my writing into two components: brainstorming topics and actual writing. In all, the experiment was very successful—it allowed me to keep up with writing 5-8 articles every week.
• Keeping Book Summaries – A lot of the ideas I generate are inspired by books I read. For over a year, I would write a 2-3 paragraph summary of every book I read, after I finished it (I still have dozens of these). It wasn’t terribly successful, as I find my writing tends to go off tangents from a minor theme in a book, rather than a restatement of the main thesis.
• Delayed Publishing – Another experiment I used was to split writing my rough drafts and editing. This was a successful experiment as it allowed me to get a fresh perspective on my writing that I would previously miss. (This article itself was a by-product of that experiment)
• Changing Publishing Frequency – I’ve experimented with several different posting routines over the five years of running this blog. Haphazard, 5x per week, 2x per week, 1x per week to today where I write approximately 2-3x per week, split over different outlets.
• Style Shifts – In addition to experiments in method, I’ve experimented with different writing techniques. List, how-to, long, concise, illustrated, researched, anecdotal, attention-grabbing headlines, interrogative, concept-oriented, solution-oriented and many more.

The challenge is avoiding complacency while still staying on a consistent schedule. Deliberate practice and skill reorganization are frustrating. I’ve often ended a work day in a bad mood after spending 4 hours working on a piece I eventually decided to abandon.

Injecting Deliberate Practice into My Work

In addition to skill reorganization, I try to inject deliberate practice into my writing. This is tricky, because writing is a moving target. Once I write about an idea, I get feedback on how to improve it, but I don’t get a do-over—every new article has to be unique.

One way I’ve tried to compensate for the shifting nature of my work, is by focusing my different writing outlets on different practice goals. Currently, my writing is split between four sources:

1. Blog articles (such as this one)
2. Newsletter emails
3. Writing in my books and products
4. Guest posts and external writing

The outlets are similar, but not identical, which allows me to craft a strategy to maximize my improvement in different areas for each one.

The blog medium keeps a permanent archive of posts, so there is more pressure to be original here. I avoid writing the same topic twice on this blog unless I can think of a substantially different angle. I use the blog to focus on the idea-generation aspect of my writing, and as a testing ground for new writing styles and topics.

The newsletter is similar to the blog, but without an archive. Since it’s younger than the blog, I use this as an opportunity to improve the technical details of my writing with existing ideas. My most popular emails have been taken from existing ideas from my 900+ articles.

This allows me to focus more on crafting better headlines and concise explanations, since I already have experience writing about the idea itself.

Books and products let me focus more on explaining ideas, rather than just attracting attention. Teaching well and being a good copywriter are related, but not identical skills, allowing me to practice explaining deeper ideas.

Finally guest posts and external articles are a more extreme example of the newsletter. Since the majority of the audience has never read the original idea before, I can use proven ideas and focus exclusively on their written execution.

For example, you can look at the progress I made with one idea, weekly/daily goals, here:

1. First, as a blog article.
2. Then, written about more extensively in my book.
3. Explained in my newsletter.
4. Written as a freelance article.
5. Finally, done as a guest post on Zen Habits.

At each stage I got feedback and was able to improve my writing. The ending evolution of the idea resulted in adding around 2000 new readers and will probably be worth several thousand dollars of revenue.

Cultivating these different outlets allows me to deliberately practice one element of my skill at a time.

Cultivating an Obsession with Mastery

My feeling about getting good at anything breaks down to two ideas:

1. Showing up, every day, is the first step.
2. Just showing up isn’t enough.

For the first part, although my frequency has changed over the years, I’ve kept my consistency largely the same. I don’t believe getting good is possible if you aren’t consistently showing up.

As for the second part, the research shows that just showing up won’t necessarily make you great. Deliberate practice and reorganization of the skill are necessary to break plateaus and go further.

Complacency isn’t just the default, it’s incredibly difficult to avoid. If you don’t push yourself to improve, nobody else will.