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Everyone and their mother has a newsletter these days.

So, yours really needs to standout.

Otherwise, it’ll dissolve into the dark abyss of internet nothingness. Your time will be wasted. Your reputation will take a hit. And, the greatest opportunity for content creators since GIFs will pass you by.

I’ve spent several years writing newsletters. For myself. For brands, business leaders, and publications. Slinging hundreds of emails has taught me a few mighty lessons about crafting an irresistible newsletter.

Today, I’m going to share thirty-nine of the best.


P.S. If you’re new to the newsletter movement, start here.

On Headlines

  1. Trigger…

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Great articles are powerfully concentrated.

They don’t waste words. They sell you with specific, original thoughts OR unique iterations of an existing idea.

Most people simply don’t make the effort to differentiate.

For example, Google “morning productivity.”

Every article says a variation of:

  • Do light exercise.
  • Get caffeinated.
  • Drink a glass of water.
  • Journal.

As copywriting sage Claude Hopkins said:

“Many articles are sold under guarantee, so commonly sold that guarantees have ceased to be impressive.”

In other words, readers ignore you because they’ve seen the same take a thousand times.

So, next time you pick a subject matter, do…

Photo by Radu Florin on Unsplash

I’ve been writing online for a little under three years now and the journey to this point has been delightful.

I’ve published two hundred articles online, freelanced for interesting founders, and spread my creative seed across the far-flung corners of the internet.

Naturally, writing and publishing so much content has come with its shares of lessons…many learned in the form of mistakes. And reading other writer’s mistakes makes the reader a better writer, right?

But I digress.

So, here is my gift to you: an ever-growing list of writing mistakes to avoid at all costs. Unlike other writing lists you’ve…

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Writing is easy.

Anyone with thoughts and a pen can craft pretty sentences.

But, can you persuade? Does your writing get the eye to dance down a page? Can you convert? Convince a skeptical reader that your words are worth a considerable chunk of time they will never ever get back?

A common problem I see with writer’s online is an emphasis on making noise over reaching specific outcomes. Often, writers try to be cute. Zigging and zagging with beautiful prose, ultimately achieving…nothing.

So, how can you make your words more attractive and engaging to readers? Brief words of persuasion…

Sex Dust packaging
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Imagine it’s 72 hours before Valentine’s Day.

You’ve done your job and purchased a dazzling gift for them.

Then, you get the dreaded “We’re sorry to inform you that your item is out of stock…SHIPMENT HAS BEEN CANCELLED” email.

Last March, I found myself in this pickle.

Frantically, I whizzed through Nordstrom’s app until my eye was charmed by something interesting. “Sex Dust,” a supplement sold by Moon Juice. Easily triggered by zesty wordplay, the product danced its way into my cart.

A rushed overnight delivery later, and, I couldn’t help but smile as a I read the black microcopy…

Black and white newspaper with “Breaking News” headline
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You see thousands of headlines every day.

Headlines when you’re doomscrolling through Twitter.

Headlines when you’re choosing a new podcast.

Headlines on book covers, magazines, and newspapers.

Headlines right here on Medium.

As a content creator, the sheer volume of headlines is fantastic. Why? Because most headlines suck. They’re lazy, boring, and abstract. They don’t respect the reader or her time.

People would rather stroke their ego to appear original/clever/smart over being clear and persuasive. This means a sprinkle of research and a pinch of effort will make your headlines shine bright in a sea of trash.

So, here’s my…

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“Thanks for speaking with us,” he said.

“We have one more question”

A small venture firm hired me to write a series of product awareness articles.

“Oh yeaaa?” I leaned forward in my chair. “What’s that?”

“So…we’re launching Monday,” he responded. “How much traffic can your article generate over the weekend? Maybe you can optimize it for SEO?”

The line fell silent. It was Friday.

“Uhh lemme take a look real quick,” I said, pretending to be checking my SEO handbook for freelancers in a jam.

“Hm. Ok. I’ll do my best.”

The article performed quite well. Many months later, it’s generated thousands of views. Steady, consistent…

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The throbbing’s back.

A stabbing pulsation rocking back and forth across my temples, playing a game of racquetball in my skull.

I’m perched up on a wooden chair in front of the counter. My back aches. For fifteen months, it’s been my makeshift workspace. Chaotic collections of notecards soaked in sink water, dried out pens, scribbled ideas on envelopes, crumbs, and a laptop.

“Hey team,” she says. “I’ll be sharing my slides for this presentation.”

It’s 10:01 AM, which means the next hour of planned “deep work” will be penetrated by her voice.

“Then if you look at what we’ve got on slide…

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Quentin Tarantino is my favorite director.

I distinctly remember seeing a Tarantino scene for the first time. The dialogue, cadence, and situation have stuck in my brain like superglue a decade later.

It was Pulp Fiction. Marvin, Vincent, and Jules are driving away from Brett’s apartment. Jules hits a speedbump as Vincent gestures to Marvin with his gun. Vincent accidentally pulls the trigger, splattering brains and bits of the skull onto the backseat, casually responding, “Oh, man, I shot Marvin in the face.”

Only Tarantino could make Hollywood swoon with a gory scene that’s equal parts hilarious and devastating.

Tarantino On Writing


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We’d agreed to meet at 9:30 a.m.

I glanced at my watch again and yawned. The office is mostly quiet besides an occasional patient checking in.

To my far right is the door I’d sauntered through hours earlier, shrouding nervous excitement in a cloud of cool.

This was my first day on the job. The sacred prize after years of hustling, studying, internships, interviews, loans, recommendations, applications, resumes, cover letters, late nights, etc.

It’s well past 11 a.m. now.

Other employees — people I’d hoped to share this moment with — barely acknowledge my flesh sitting among them.

I’m getting…

Jonah Malin

Pending humble-brags. To write pretty words that last→

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