The 6 Standout Habits Of 100 Legendary Writers That Guarantee Great Writing

Dickie Bush & Nicolas Cole

Ultimate Guide Table of Contents

Ahoy and happy Monday!

Welcome to another week of Start Writing Online—where every week we dive into 1 of the 10 biggest problems all writers face:

  • Distractions
  • Over-editing
  • Perfectionism
  • Procrastination
  • Self-confidence
  • Generating ideas
  • Impostor syndrome
  • Writing consistently
  • Finding time to write
  • Loose feedback loops

(And, of course, if you want to crush all 10 of these AND master the fundamentals of Digital Writing in just 30 days, we'd love to have you in the next cohort of Ship 30 for 30!)

This week, we want to help you get rid of those pesky distractions.

And what better way to dive in than by studying the routines of legendary writers?

Dickie spent hours studying Gary Halbert, Jerry Seinfeld, David Ogilvy, Ernest Hemingway, James Clear, Maya Angelou, and more. They all had their own quirks. But surprisingly, a few things kept showing up time and time again.

The most prolific writers of our time knew one essential thing.

The best writing is not a result, it’s a BYPRODUCT.

These authors didn’t sit down and go from blank page to the next “Great American Novel.”

Instead, they built their daily writing habit into their life. Writing every day was easy for them because of the way they did everything else. And since Dickie started following these habits he went from writing a blog that only his Mom read, to growing a Twitter following with more than 351,700 followers and growing his newsletter to over 50,000 subscribers.

Turns out, these systems work.

Let’s dive into 6 habits.

Habit #1: Take long walks

Steve Jobs, Charles Darwin, and Mary Oliver—all “creative walkers.”

Daily walks were the staple of their creative process.

  • Thinking
  • Listening
  • Outlining
  • Observing

95% of their writing happened during long walks. They weren’t slaving over a keyboard for dozens of hours wondering if what they had to say would be worth reading. By the time they sat down to type, they knew exactly what to say.

Most of my writing happens when I go for walks. Because when I sit at my desk and try to crank my brain—nothing comes out. It doesn’t work. And if I get writer’s block or I’m just trying to think an article through, I go for a walk. I go for 2 or 3 of them in a day. That’s where all the “writing” happens. -Morgan Housel, author of “The Psychology Of Money,”

Give it a try.

Stack your walk on the back of something you are already doing. It doesn’t matter when. It could be right after you wake up, just before lunch, or between meetings, just pick a time and go.

  • Map out your route ahead of time.
  • Leave your phone behind.
  • Give your mind space.
  • And then just walk.
  • When you return, sit down to write.

We are willing to bet your creativity will skyrocket.

On to the next habit!

Habit #2: Capture ideas—everywhere

The world's biggest lie: "I'll remember that idea later."

Each of these great writers treated every idea as precious and captured it immediately.

  • Quick capture on their phone
  • Whiteboards in the shower
  • Notebooks next to the bed
  • Post-it notes in their pocket

These first 2 daily habits made coming up with ideas easy something that happened with zero effort. By simply going about their day, their brain was free to think creatively. Staring at a blank page? Never a problem for them.

When you give your mind the freedom to think, without the burden of holding thoughts in your “Random Access Memory,” you will start having more ideas than you know what to do with. But this is only possible when you give yourself a place to capture them—wherever you are. So, when you go on your walk, be sure to grab something to capture those ideas!

Then once you have all those ideas, it’s time to write, which takes us to the next habit.

Habit #3: Write on a timer—every day

If you only write when you are ready to write—you’ve lost.

You will start and stop. Then you will start and stop again. You will never build the consistency you need to get the outcomes you want.

The results will speak for themselves.

Compare that to, Jerry Seinfeld—a billion-dollar comedian, and Gary Halbert—a billion-dollar copywriter. Both of these legends had a simple routine with 1 rule.

  1. Set a timer for 33:33
  2. During that time, you could do anything except get out of your chair

And this took the pressure off writing.

For the first few minutes, they would stare at the wall. They would sip their coffee and think about all the other things they would rather be doing. But at some point, they'd start writing.

The timer let them know the torture would end soon.

During their breaks, they would walk around, have a quick snack, and do anything else but write. And during this time, inspiration always struck. Then, at the end of the day, they wouldn't say "I wrote until I got tired." They would say "I wrote for six sessions today." This made it easy to keep momentum. The timer made it easy to get started, and the daily recap made them feel a sense of accomplishment.

Day by day, these sessions compounded.

So, hop on Amazon and buy yourself a $3 kitchen timer. Then for the next 3 weeks, set the timer for 20 minutes and write for one 20-minute block every single day. Over time you can increase your time to 2 blocks, 3 blocks, and so on.

Each week you can look back and say with confidence, exactly how much time you spent writing—which makes it easy to keep the momentum going.

Let’s keep going.

Habit #4: Ruthlessly block distractions

95% of writing is simply avoiding the internet's distractions.

Your willpower is no match for the endless pings, dings, and zings the internet loves to send us. Reddit, YouTube, and TikTok will all pull you into a deep rabbit hole that will keep you from writing. But only if you allow them to.

The writers Dickie studied would go a long way to isolate themselves from interruptions.

  • Maya Angelou would rent a secluded hotel and take all the furniture out.
  • Matthew McConaughey spent 50 weeks in the desert with just his journals.

If the best authors in the world can’t overcome distractions, it’s a signal for you and me to stop relying on willpower to avoid the noise.

  • Download Cold Turkey and reclaim “internet time.”
  • Use a second phone, solely for the purpose of taking notes.
  • Go analogy. Grab a pen and a journal and do things the old-fashioned way.

Get in front of the noise, and ruthlessly block distractions.


These last 2 habits will help you turn average writing into legendary writing.

Habit #5: Be 100% content to appear clueless.

Each of these writers had a complete lack of ego.

They were endlessly curious—never afraid to ask "stupid" questions. This made them learning machines, always inhaling new information. You can literally feel the curiosity in their writing.

Without an ego, these writers would dive head first into any new topic as complete beginners.

By learning and studying different topics & fields, they could combine ideas in a way no one else could. They didn’t think they had to be an expert to write about something. They simply learned something and then wrote about it—way before they were “qualified” to do so.

The smaller the ego, the better the writer.

Don’t be afraid to look like a beginner.

Habit #6: Constantly seek objective feedback

Most writers never hit publish because they're "perfectionists."

But perfectionism is 100% an ego problem. You are assuming people are going to comb your every word, waiting for mistakes. Newsflash: they aren't.

Instead, hit publish before it's ready

The truth is, your writing will never be ready. So get it out into the world. Then, listen carefully to what your readers have to say.

Don't ask for feedback—ask for advice

People are uncomfortable giving feedback, so when getting advice (instead of feedback) ask where things are boring, confusing, or for anything that makes the mind start to wander.

Then ask two more questions:

  • What is the 10% I must keep?
  • What is the 20% I should cut immediately?


And here's the 1 big realization you should have by now.

The best writing is not a result.

It's a byproduct.

By carefully crafting (and following) a daily writing system, great writing is guaranteed.

And these legends provide the best example!

That's it for today!

Chat next week!

–Dickie Bush & Nicolas Cole

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