Everyone and their mother has a newsletter these days.

So, yours really needs to stand out.

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 39 of the best.

Enjoy.

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

🔍 Related: I dare you to write your newsletter

Headlines

1. Trigger words like ‘Sex’ and ‘Fuck’ in your headline = high open rates, high unsubscribes. Use them with caution.

2. Your headline is the ‘ticket on the meat.’ Make it the most remarkable thing the reader comes across all day.

3. Tell the truth. Weave your headline subject matter into the body of your email. For example, if my headline is ‘*Curb Your Enthusiasm theme starts playing* Pretty, pretty, pretttaaay good SEO advice’, you’ll be damn sure my email is about SEO.

4. Keep it short.

5. Spend 15 minutes perusing through your promotions/spam emails. Brands often utilize proven, old school marketing tactics in their subject lines. They pay someone to write their headlines. If you see anything with standout, “borrow” them...

Writing

6. Make your first sentence noteworthy: “The sole purpose of the first sentence in an advertisement is to get you to read the second sentence.” — Joseph Sugarman

7. Say it. Then say it less. OR, know when to stop. Remove unnecessary words. Avoid long, winding introductions.

8. “It’s not about the news — it’s about the letter.” — Ann Handley

9. Entertain yourself. But…but…the precious reader. “THINK ABOUT THE READER”, your subconscious is screaming.

Yes. However, my early emails solely in service of readers were boring. Now I write what I want to read. Reflect on things that make me laugh or think, or walk away inspired. The results speak for themselves.

10. Whenever possible, address the reader directly. Leverage second-person to be intimate.

11. Cliffhangers and post scripts build continuity.

12. Be conversational. As if you’re sitting in a bar, talking to your old friend.

Editing

13. Please, please proof your copy. Readers pointing out grammar errors is funny the first time. But not the 12th time.

14. [Ctrl + F] search for filler words like ‘that.’ And…‘like.’

15. Distill your text into its simplest, clearest, easiest-to-understand form. Put fluff on the chopping block, and slice its head off.

16. Always send yourself a test email and triple-check links.

Formatting

17. Sacrifice glitz and glamour for readability.

A subscriber once let me know that my article font was too small. He was right. I’d been taking an unnecessary approach to formatting with right texts aligns and tiny fonts to be unique.

Who cares about pretty formatting if people can’t read the thing?

18. Readers scan. Use bold words and italics to highlight important points (though, too much contrast becomes distracting).

19. Cut “Learn more” out of your vocabulary. Is there a more basic, abused CTA? Instead, write your CTAs and buttons as a continuation of your text.

Here are a few of my highest performing buttons:

• Read on?

• Mom?

• Do it. You won’t.

• An ounce of sauce covers a multitude of sins.

• “Spot on, Jonah.”

• On writing copy that breaks the rules

20. Don’t be afraid to break the rules.

Visuals

21. Go custom. Plain text emails are lazy and clunky. Use Canva to whip up interesting imagery supporting your words. Toss in a few GIFs. Be different, damn it.

22. Newsletters are more than words. I spend about an hour each week crafting visuals.

23. Avoid emojis. Personal preference, but emails with emojis strike me as unpolished.

24. Create a visual engine. My email headers match my website. Which matches my article headers. Which matches my social profiles. A pinch of effort gives you a recognizable content storm.

Subscribers

25. Make subscribing ridiculously easy. Never bury the form on a landing page. Don’t overwhelm with text and visuals. Hold their hand and guide them to your intended action.

26. Establish an email opt-in process.

27. Write a kick-ass follow-up email. Preview the type of content they can expect. Don’t let people go months without hearing from you.

28. Community and word of mouth drive subscriptions. It’s no coincidence that mentions from other newsletters/creators/publications always lead to a generous bump in subscribers. Which also means…

29. Play nice. I often link to fellow writers’ newsletters, books, and announcements. They do the same.

30. Sprinkle your CTAs everywhere. On your website. In your email signature. At the bottom of your articles. Spread your CTA seed far and wide.

Unsubscribes

31. There’s a special place in hell reserved for people who unsubscribe from my email list (is what I used to think). The truth is, a small, engaged, well-defined group is more valuable to you. Let the unsubscribers go.

Keep calm and carry on.

Consistency

32. Whether it’s daily or monthly, make a promise and keep it. If you’re going for the “send whenever I feel like it” approach, good luck. That’s reserved for the James Clears and Ann Friedmans of the world.

33. Consistency keeps you top of mind. Eventually, readers will look for you.

34. Resist the urge to drown every couple of emails in gasoline and dramatically toss a match on it all. Make incremental adjustments. This is an ultra-marathon.

35. However, don’t be afraid to pivot. My newsletter, Gobsmacked, began as a delicately curated list of articles, links, and videos for writers. But I’ve changed. The newsletter reflects this evolution.

🔍 Related: The magic behind newsletters is simpler than you think

Lasting success

36. Set realistic expectations. Take the time to figure out how many hours you can spend writing, editing, and refining your newsletter.

37. Build an ecosystem. Ask subscribers for feedback. Respond to their questions/concerns/suggestions. Invite them into your community.

38. Study the greats in your niche. You don’t know what you don’t know.

39. Care. About the copy. About your readers. A newsletter is your product. An extension of your name and brand. Give it everything you’ve got.

There you have it folks; 39 lessons on writing a newsletter that people actually want to read.

You’re welcome.

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