The 3 Most Important Writing Lessons I’ve Learned in 3 Years of Online Writing

I’m coming up on my third anniversary as a Medium writer (it’s in March), and it’s been a wild ride. 16,000 followers, 3,000 email subscribers, and $50,000 later (yikes! Where the hell did all that money go!?), and I’m finally starting to ask some big questions about what is making it all possible.

Most of what made it possible was out of my control, of course. I didn’t find Medium, invent the internet, or manufacture the Apple Macbook. But there was a lot within my control — and there is a lot within your control, too.

To the upcoming writers of Medium, Amazon Kindle, their own blogs, or somewhere else, here are the 3 biggest lessons I’ve learned in my writing career.

1. Writing frequently really matters

“Start writing, no matter what. The water does not flow until the faucet is turned on.”

― Louis L’Amour

You know it. You love it. It’s the most common writing advice in the world: Write every day.

I’m repeating it to you now because the simple fact of the matter is that you cannot get better at something you don’t practice.

I actually don’t think you need to write every day. I never have — I write anywhere from every day to once a week — but you do need to write regularly.

The right frequency for how much you should write is enough that it feels routine. If opening a new document or hitting the submit button feels like a special effort, you are not writing enough. Write enough until writing feels boring and then keep writing.

2. Getting better at writing matters more

“The difference between the almost right word and the right word is really a large matter. ’tis the difference between the lightning bug and the lightning.”

― Mark Twain

As several Medium big shots have pointed out, writing frequently is not enough. If you never do anything to improve your craft, you will spend year after year and decade after decade producing writing no one wants to read.

This lesson has been a tough one for me to learn. I’ve been on Medium working my ass off and only have 16k followers, which sounds like a lot until I compare myself to Amardeep Parmar, who went from 0 to 13k followers in a single year.¹ Now that’s audience growth.

What fuels audience growth?

1. Writing often
2. Writing better
3. Doing business better

Doing business better is the third point in this article, so let’s discuss writing better.

My favorite way to develop my writing is to read craft books and excellently composed nonfiction books.

Most craft books are merely a tedious repetition of the same tired old advice (“don’t end a sentence on a preposition,” “write every day,” “keep your paragraphs a reasonable length”). Still, there are a few that have transformed my writing overnight. These include Stephen Pinker’s Sense of Style⁰ and William Zinsser’s On Writing Well.⁰ If you haven’t read these books, do so ASAP.

As for excellently composed nonfiction books, you’ll have to go to your local library and allow your sense of taste to guide you to books you consider well-written. As you read them, reflect on how the composition enhances your enjoyment of the subject matter. Study these books. Sleep on them. This kind of mental activity is fertilizer for your writing. As you do more of it, you will find your writing improving organically.

If you have to sacrifice some of your precious writing time for studying time, do it. Frequent writing without craft improvement is nothing. (But not too much. I spend 20% to 30% of my working time studying, compared to 50% writing.)

Before concluding this section, I will also touch on research. For several years, I didn’t worry so much about research, which clearly reduced my writing quality. I knew what I was saying was true because I read it out of well-researched books, but I didn’t cite my sources, and that was a rookie move. Take the time to cite your sources. If you can’t find any, search some up at scholar.google.com. Google Scholar is a godsend.

3. Good business fundamentals matter most

“It’s called “best-selling author,” not “best author.””

— Robert Kiyosaki

In dark, forgotten corners of the internet, there is some magnificent writing lying undiscovered. Some of the best short-form work I’ve ever read has been hosted on defunct Bloggers, forgotten HTML sites, and buried in Reddit comments. The authors of these articles were incisive thinkers, talented writers, and meticulous editors. And because they didn’t have business skills, it didn’t f*cking matter.

Back when Twilight was popular, people loved to roast Stephanie Meyer for her sub-par writing ability. Stephanie Meyer got famous, while many better writers didn’t, because Stephanie Meyer learned the business of publishing novels.

Hell, I’m an example of this. My writing isn’t the most beautiful writing you’ve ever read. It doesn’t move you to tears. I have my occasional moments of intellectual incisiveness, but I more frequently have moments of tone-deafness and uncomfortably long sentence composition. Why am I earning thousands of dollars a month writing online while many other more talented writers are not? I know and practice good business fundamentals.

These are the business fundamentals an online writer needs to practice if they have a hope of making money:

1. Publish work on the platforms where writers are making money. All the work in the world won’t matter if you’re publishing on a platform that doesn’t turn a profit.
2. Market your work in a way that will make you money. Write whatever you want, but write it with a title readers like to click, format it in a way readers like to read, with stock images people like to click, and add tags that readers like to search on. Your article's body is your chance to be an artist, but you should consider the packaging of your article a cold business calculation.
3. Make business decisions that increase your chances of making money over the long term. Examples include: Building a mailing list, releasing products, joining writer communities, and participating in projects that expand your horizons.

I hate to burst your delusional bubble, but basically every famous artist ever understood these things. Michaelangelo was one of the greatest artists of the Renaissance… and also a ridiculously clever businessman. He initially went off to study grammar, but he didn’t like it, so he became a painter. He leveraged the connections of his father, a local administrator, to get early work as a painter. He spent many years collecting painting clients and building his painting business. After training apprentices to paint and starting a successful painting business, he apprenticed under legendary sculptors, then going on to gather sculpting clients and train sculpting apprentices. After a lifetime of honing his artistic and business acumen, he was able to convince someone to pay him a lot of money to work on the Sistine Chapel. Prodigiously skilled, historically famous, and filthy rich.²

For some reason, many writers feel that practicing these business principles is selling out. This sentiment strikes me as total nonsense. Getting in front of readers and creating what they want continually improves your art quality, turning you into a progressively better artist each year. There’s a reason professional artists tend to be better artists than unpaid amateurs — they’re a) exposed to the feedback they need and b) have all the time they need to improve on that feedback.

This is, in fact, the reason I’m a professional writer. If making money were a priority to me, I would have stayed in tech startups and became an executive consultant. Those guys make bank. I didn’t want to be an executive consultant for startups and make bank. I wanted to write. And the people who get the most time to write, the most feedback on their writing, and the most opportunity to improve their writing, are professional writers.

I think it all goes back to childhood. In childhood, our well-meaning ignorant parents taught us that businessmen are rich while artists starve. We then watched our artist friends get music degrees and end up working at Wendy's, so we never questioned this lesson. As a result of mysterious psychological processes, we transform this lesson into the lesson “rich artists are not real artists.”

It’s time to unlearn that lesson. The best artists are often also the richest ones. It’s “best-selling author,” not “best author,” for a reason.

Becoming a successful writer is one of those things that’s stupid easy to preach about and stupid hard to learn. I’ve been writing for three years and am considered a mild Medium success, but there are still so many subjects I don’t understand and so much I am doing poorly. It will be ten years before I figure out what the heck is going on.

So if you are feeling bad about your performance, don’t. Writing is hard, and you’re not going to figure it out anytime soon. Just get that next article out, and then do it again. We’ll figure out the rest.

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1: Comparing yourself to others to make yourself feel bad is a huge waste of time. If I catch anyone comparing themselves to someone else just to beat themselves up, I’ll beat you up for you.

Comparing yourself to others to prompt introspective questions that ultimately lead to improved performance, though, is worthwhile. It’s painful to learn lessons yourself; much better to let others learn them for you.

2: Yes, I am aware this is not true of literally every artist. Van Gogh leaps to mind. But Van Goghs are the exception, not the rule — and even Van Gogh was an experienced (albeit incompetent) art curator and businessman.⁰