First drafts are shit – and 10 other lessons that will instantly make you a better writer

Mastery of any craft is elusive, but mastery of writing may be the most elusive of all. There really is no point at which someone can say they’ve “mastered” writing – you can only creep infinitely closer to it. We can’t objectively measure or score language like we can in golf or chess. We only recognize great writing when we read it. And no matter how much praise or respect a writer may receive, he or she will always admit that their ideas never quite align perfectly with what ends up on paper (or on the screen.)

Such uncertainty drives many away from the pursuit of writing, but nobody can fully escape it. We’re not all journalists or authors, but we have emails to send, memos to write, and presentations to give. Fortunately, plenty of remarkable writers have shared (either directly or indirectly) their priceless insights which can help make this tough job a bit easier to bear.

Since I started writing for myself and on behalf of clients, I’ve set aside time each day to study legendary writers in hopes of capturing the essence of what separates their language from the clutter. There’s no point in keeping what I’ve learned to myself, so I decided to go through all the notes I have and condense them into what I’ve found to be the 11 most valuable lessons.

Here they are:

Read voraciously – Samuel Johnson 

Johnson said that “The greatest part of a writer’s time is spent in reading; a man will turn over half a library to make one book.” This lesson is not just reserved for authors, though. It applies to business proposals, job application essays, and blog posts. Whether we need factual evidence or stylistic influence, books lay the foundation for the written word. There’s no telling how many ideas and lessons there are to be discovered in books, even ones unrelated to what we write, that simply can’t be found on TV or in everyday life.

Have something to say – Arthur Schopenhauer

Schopenhauer once observed that there are two types of writers: those who write because they have something to say and those who write for the sake of writing.

If you ask a teacher how to become a better writer, they might suggest going to writer’s groups, contributing to a publication, getting an MFA, or just spending hours writing. But they never tell you to go do interesting things. This is what Schopenhauer is talking about: no amount of literary skill can conceal a lack of knowledge or experience.

Example: a grammatically flawed but passionate firsthand account of
being detained overseas is likely more captivating than a “professional”
journalist’s coverage of the same story. Experience provides us with a perspective and a unique voice. It doesn’t just give us words; it gives us something to say.

Rewrite somebody else’s work…word for word – Denne Bart Petitclerc

Denne Bart Petitclerc was abandoned by his father at the age of five, after which his mother sent Denne and his older sister to an orphanage in San Jose, California. Semi-illiterate, Denne was known to have transcribed Ernest Hemingway’s short stories word for word in order to get a feel for his style. A stroke of luck even allowed Petitclerc to meet his childhood idol. Petitclerc would go on to work for several newspapers and eventually became a Korean War correspondent for the Santa Rosa Press Democrat as well as a screenwriter for several TV series and films.

Bottom line: If an illiterate orphan can learn to write well, so can you and I. Don’t worry initially about imitating anther writer. After enough practice your own voice will emerge.

Understand the whole before addressing the particular – Robert Greene

Greene has earned a reputation as perhaps the most prolific researcher of any author alive, a skill that’s exemplified in his books. For Greene, writing is the easy part of being an author. The challenge is wrapping his head around a raw, complex idea. So often we start writing without a game plan – before we know it we’re bogged down by insignificant details on the first page and end up calling it quits after 150 words. Readers can tell when a writer has constantly bounced back and forth between research and writing: sentences are jumbled, there’s no sense of coherence. But organizing all facts and research materials before setting out to write eliminates confusion as to how a piece should be structured. 

Eliminate distractions – Cal Newport

With a Ph.D. in computer science and five published books, Cal Newport understands that writing demands long periods of uninterrupted focus. In his book, Deep Work, he argues that the skill of intense concentration will increase in value as our culture becomes more and more distracted. This doesn’t mean we have to go off to some remote location in order to be productive – unplugging will usually suffice.

“Start with training your cognitive fitness before diving into your first big writing project just like you’d train your cardiovascular fitness before trying to run a marathon,” says Newport. “In other words, National Novel Writing Month would be a lot more successful if it was preceded by National Don’t Use Social Media Month.”

Cut off the fat – William Zinsser

“Don’t say you were a bit confused and sort of tired. Be confused and tired,” says Zinsser. “Good writing is lean and confident…every little qualifier whittles away some fraction of the reader’s trust.” This advice might seem petty or insignificant, but straightforwardness has a profound effect on a reader. These qualifiers that Zinsser mentions are like training wheels for writing: we use them because we’re unsure whether our language is valid enough to stand on its own. But once we ditch them they’re gone forever. 

The first draft of everything is shit – Ernest Hemingway

Trying to write a polished piece from the get-go is a recipe for frustration. Hemingway even rewrote the ending of A Farewell to Arms 39 times before he was satisfied. There’s no need to get flustered when a masterpiece doesn’t pour forth from your fingertips like Hollywood portrays. It’s reassuring to know that even the most elite writers looked at their work and knew it sucked; however, what separates them from the the amateurs is the willingness to sit back down and get it right.

Seek out negative feedback – Tim Ferriss

Ferriss says that the first question he asks when receiving feedback on his books is “What should I cut?” He’s known for ruthlessly cutting anything that’s not essential both from his own work and the work he edits, a lesson we can all learn from. It’s tough hearing someone tell you those sentences you painfully strung together just aren’t that good, but this ego check is exactly what we need to mature as writers. It’s been said that when someone tells you something is wrong with your writing, they’re usually right. But if they tell you how to fix it, they’re usually wrong. Think quantity before your give yourself the quality cop-out. You can always cut.    

If you’re stuck, write a letter – Anne Lamott

Even after extensive research and multiple drafts, there are times when putting one word after another can seem unmanageable. This, Lamott says, is when we should convey what we want to communicate in the form of a letter to someone important to us. By explaining what you want to tell them in an informal way, it can provide the raw material needed to create a more coherent, polished piece of writing. Another alternative is to call someone to talk on the phone about the topic. You’ve never heard of anyone getting “talker’s block.” Spill your guts out, then turn it into an outline. Let it evolve from there.

Exercise strenuously – Ryan Holiday

For centuries, writers have relied on physical activity to unglue their minds. It’s like the figurative reset button on the creative process – once you hit a wall, intense exercise brings in a new wave of ideas. Holiday goes for a 6-8-mile run every single day after he finishes his morning writing. But he runs for something other than just the  physical benefits – “It makes me better at my job,” he says. Holiday even recalls rushing home during a run 2013 because he came up with the introduction to his book, The Obstacle is the Way, in the middle of it. All the thoughts that once seemed clumped together seem to sort themselves out after exercise. That’s because there’s nothing else to dilute them. It’s you versus yourself, which can be frightening until we realize it’s exactly what we need to take our productivity to the next level.

“Faire et se taire” Translation: Shut up and get on with it – Gustave Flaubert

At the end of the day, all the advice, workshops, and books in the world can’t save us. You know what to do next. 

A Few Bonus Tips

Use a thesaurus

It’s easy to fall into a routine of repeating the same words over and over. Aside from reading lots of books, a thesaurus is the best tool to revitalize your vocabulary. Apple even has a great thesaurus app that comes built in to every Mac computer. Just don’t go overboard. Rule of thumb: if you have to look up the definition of the word you think sounds cool, you probably shouldn’t use it.

Keep a commonplace book

When you find a good quote, idea, or piece of advice, write it down. You never know when you might need to reference it later. This simplifies the research process, especially if you’re a pen- and-paper type of person. I write my notes on 3×5 index cards and organize them by category. 

Read your work aloud

Mistakes are often easier to hear than see. This exercise can also save you from sounding pretentious or artificial. Learn to trust your ear.


Here are 5 books to base your life on, plus 7 strategies I stole from marketing geniuses to promote your work.


One thought on “First drafts are shit – and 10 other lessons that will instantly make you a better writer

  1. These are helpful. Notice how I cut out “so,” per William Zinsser.

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