How to Write for a Living

How to Write for a Living

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How to Write for a Living
How to Write for a Living
15 absolutely vital lessons I've learned as a working writer

15 absolutely vital lessons I've learned as a working writer

Learn from my growing catalogue of trials and errors.

David McIlroy's avatar
David McIlroy
Mar 28, 2024
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How to Write for a Living
How to Write for a Living
15 absolutely vital lessons I've learned as a working writer
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I’ve been an online writer and creator for a while now.

Let me tell you, it’s a rollercoaster. I’ve hit plenty of highs along the way, and I’ve dragged myself through just as many lows. Triumph leads to trial, trial leads to triumph, and around we go.

In all of it, though, education is the outcome. Every day, I discover a little bit more about myself and the game we’re all playing here on the interwebs.

Here are 15 key lessons I’ve learned as a writer so far.

1. Authenticity breeds loyalty

Why am I continuously drawn to the work of my favourite creators, regardless of any mistakes in their writing?

Because their messages are more important than how they’re delivered.

Read that again. Slowly.

I care far more about what the writer’s trying to say than how they go about saying it. The effect’s more important than the execution.

Don’t get me wrong – if a writer’s work’s constantly filled with errors, I’ll start to wonder how much they really care about it.

That’s when I’ll stop clicking into their stories or opening their emails. I may even be tempted to boop the unsubscribe or unfollow button.

But if I know my brain’s going to get a generous dose of insight by reading a writer’s words, I’ll read ’em all day long.

2. Habit first, rhythm later

If I can make it past the six-week mark with any routine activity, I know the habit will have taken root.

Diet, exercise, drinking water… you name it, and if you can stick at it for a period of time, it’ll become ingrained in your lifestyle.

The same goes for writing.

Getting into a writing rhythm’s never easy in the beginning. Those sessions in the early days when you feel like you’re getting nowhere are tough. You feel like you’re posting into the void, speaking to no-one, making zero progress.

But if you can stick with it long enough to form a habit, it gets a heck of a lot easier.

Suddenly, you’ll yearn to write each day. You don’t feel complete without that daily session tapping at your laptop keyboard.

And before you know it, you’ll have smashed your once-lofty writing targets, with brand new ones on the near horizon.

person using laptop computer
Photo by Christin Hume on Unsplash

3. The rule of 7

Talking more about your product, brand or service = more sales.

Even the process of explaining what you’ve learned as a writer needs to be done consistently. You may need to share the same lesson at least 7 times before the message gets through to your audience.

Heck, even using the number 7 in your content (as part of your headline, 7 teachable points, etc) likely has some impact on the effectiveness of your message.

After all, Miller’s Law states that, “The average person can only keep 7 (plus or minus 2) items in their working memory.”

4. Iterate your way to success

The point is, if you want to improve, you have to journey through multiple iterations.

Which means you’re going to fail a lot along the way.

But that’s just part of the process, right? You either stick at it, or you don’t.

Whatever it is you’re doing, you’ve got to:

  • Practice

  • Expect failure

  • Learn from it

  • Celebrate the milestones

“The greatest teacher, failure is.” ~ Master Yoda

5. Harness emotional writing

Don’t just spew your thoughts onto the internet like an angst-ridden teenager chasing heart emojis on Bebo in 2006.

Write your emotion-laden draft, then walk away.

Give yourself time to settle.

Then, when your mind’s cleared, come back to it. Read it again. Make necessary edits. Come up with a killer headline.

Then hit the publish button.

6. Bring inspiration directly to you

If you’re ever stuck for inspiration, just open up your inbox and start reading.

It won’t take long before inspiration bleeding through the writing of other creators stirs up your imagination, and then filters through onto your page.

Newsletters are a fantastic source of killer content ideas.

Subscribe to a few today and start digging.

7. Master your headlines

I constantly grapple with what makes a good headline good.

This grappling manifests as never-ending experimentation. I look back on the headlines of old articles, analyse what worked and what didn’t, and try again.

And again. And again.

Persistence eventually pays off on this platform, and that goes double for headline experimentation.

If you ask me, there are generally 4 key elements to every good headline on Medium, Substack, or anywhere else on the interwebs:

  • Intrigue

  • Emotion

  • Numbers

  • Specificity

Not in that order, of course.

But if you can make your headlines intriguing, incite emotion in your reader, and zero in on some specificity (while including a number), you’ll give your article an above-average chance of getting read.

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