Email marketing can be extremely effective — if you can get someone to open the email. One-third of your recipients will open the email based on your email subject line, so be creative, be smart, but most of all, avoid these 12 mistakes.

As we’ve noted before, email marketing is truly one of the keys to effective content marketing. The most critical element is the subject line. It’s your elevator speech. Your foot in the door. Your opening line. Harkening back to my days as a direct mail copywriter, it’s what gets people to open the envelope. So it had better be good. Gosh-darn good.  And the first step to doing that is to learn from others mistakes.

Charlie Meyerson: He pioneered Chicago news email

For how to do email marketing right (and in this case, wrong), we turn to a guy who’s been writing email dispatches for a gazillion years: Charlie Meyerson.

I saw Charlie speak at recent a Wine & Web event hosted by the fine folks over at Orbit Media. Charlie’s an old-school word guy like myself — a long-time journalist / writer / wordsmith, currently vice-president of editorial and development for Rivet Radio. (You’ll definitely want to check out the concept behind Rivet Radio.)

Charlie cut his teeth on email marketing with the Chicago Tribune. He launched and ran the Chicago’s Tribune email news services, Daywatch and Tribute Alerts from 2000 to 2009, where he achieved a 60% click-through rate.

The guy was (is) verrry good at the email game. So let’s dig into the mistakes gleaned from Charlie’s presentation.

Learn from these email subject line mistakes

Charlie notes the key to all email success was very simple: stronger headlines. Here are some mistakes to eliminate on your way to crafting those money-making missives:

1. Neglecting to write for the ear. Headline writing is like writing for the radio. You want to capture someone’s attention. Fast. Would it capture your attention if you heard it on the radio?

2. Making emails too wordy. Charlie’s a man of my own heart, citing Will Strunk’s immortal phrase “Omit needless words” as a key to writing a good great headline. You love your words, but sometimes you just gotta murder your darlins’. Omit. Needless. Words.

3. Inserting your organization’s name in the email subject line. Why waste the space? Your from field will reveal where your email is coming from. The subject line is your chance to tell your reader what the email is about.

Don’t include your name in subject line. Source: Charlie Meyers

Graphic: Charlie Meyerson

4. Repeating the same subject day-to-day. If you send the same subject message, people will fail to see what’s unique about the contents — especially if they’re reviewing your emails en masse. (I set all trade emails aside and review them at the end of the week. If I received the emails listed below, I would delete them all.)

Don't repeat subject line

Graphic: Charlie Meyerson

5. Including series # or dates in the subject line. No one cares how many issues you’ve send. And new readers may be turned off by a high number (“I’ve missed a lot, and I don’t like coming in at the middle of the movie.”)

No need for the date in your subject line, either. (It appears automatically through your email interface.)

You don’t need to include how many are in the series. And you surely don’t need the date in there (it kinda appears automatically through your email interface).

Want to see a few examples? Take a look at the graphic below for mistakes #3 – 5.

Don't include date in email subject line

Graphic: Charlie Meyerson

6. Choosing a weak phrase for your first element. What’s the most important word in your headline? Find it, and make it the word storming your Normandy beachfront.

7. Ignoring your click-through metrics. This is all about language, right? So see which words actually inspire your readers. Certain words always inspire clicks, yes. But what are your readers looking for? Consider:

Shipwreck in subject line

Graphic: Charlie Meyerson

Charlie shared this Tribune email headline that got a big response. Why did it have such impact? Through repeated experience, his team concluded it was the word “shipwreck.”

By analyzing reader clicks, Charlie and his gang discovered their audience was drawn to any headline with the word “shipwreck.” (That explains my headline, right? ; )

Everyone loves a good shipwreck — except for the victims, of course. It’s why you’re powerless to avoid watching this clip.



8. Failing to pay off a curiosity gap headline. Charlie rejects the phrase “clickbait” for headlines. He says there are just good headlines (headlines that connect content to the maximum number of people to whom it’s useful and relevant) and bad headlines (which fail to connect content with people who’d find it useful and relevant.)  

The “curiosity gap” headline examples below raise curiosity about the content and inspires a click.

Curiosity gap headlines

Graphic: Charlie Meyerson

These “clickbait” headlines aren’t bad. They’re actually an excellent technique. But the content has to satisfy the curiosity they inspire.

9. Using acronyms. Unless your metrics say otherwise, avoid the CPM, B2B, SEO, CTR and other acronyms of the world. Not sure if LOL counts. (LOL.)

10. Boring your reader (and yourself). The world’s number one rule in writing. period. The easy way to avoid this? Start with yourself. If you’re bored with content or its headlines, don’t expect anyone else to be excited. Make yourself laugh. Make yourself cry. Seize the day, O Captain My Captain!

And here are a few other mistakes beyond Charlie’s presentation:

11. Exceeding the character count. Most email desktop inboxes cap the number at 60 characters, and mobile apps at 25-30 characters. Keep it tight.

12. Using characters or words that inspire SPAM detection. Special characters such as $, #, % should be avoided.

You’ll find many opinions on which words trigger SPAM, and some lists I’ve seen go too far, including too many terms.

Most email servers typically screen your emails for SPAM potential, so be sure to check that before you send. Beyond that, my advice would be to avoid phrases like “FREE” and “BUY NOW” — essentially, avoid the cheesy phrases.

Enough of the mistakes! How-to tips for writing email subject headlines that inspire click-throughs

You’ve got your checklist of things to avoid. So how do you write the winning headlines? We’ll give you a few more nuggets from Charlie, as well as links to great articles on the subject.

Reverse the mistakes you just read. First, turn all the things you’ve just read upside down and apply the lessons learned from the top mistakes. Write direct headlines. Omit needless words. Check your click-through metrics. (You get the idea.)

Use familiar names. Charlie noted proper nouns really capture people’s attention — but only if they’re familiar. For example, you’d only use a CEO’s name if it was a high profile CEO like Richard Branson. Otherwise, find a different description to explain why a person, place or thing is relevant.

Write “how-to” or “list” headlines. This one is from Winbound. “How to” or “list” headlines always do well on search engines and social media. Our own headline below “How to Fix a Lazy Eye” has generated over 80,000 views.

Lazy eye headline

Pro Tip: Use the Headline Analyzer Tool

This a great score-based tool from the fine folks at Co-Schedule. It automatically deducts points if you don’t use a “How To” or a list in the headline.

Headline analyzer

Headline Analyzer from Co-Schedule

Great articles on how to write the greatest email subject lines

Here some great how-to articles and some examples:

Improve Your Open Rates with these 12 Subject Line Tweaks – Constant Contact’s take on what works. They’ve probably seen a few success stories or two.

How to Write a Headline that Won’t Get Ignored: 7-Point Checklist – Orbit Media’s post on headline writing in general, but it definitely applies and includes tips from some of the best in the biz.

18 of the Best Email Subject Lines You’ve Ever Read – Nothing inspires creativity like seeing great examples. Check out this compilation from HubSpot. You’ll laugh, you’ll cry, you’ll order pizza.

This list could go on forever. The key is that you now know what the rules of the game are. You’ve got the fundamentals in place for the mistakes to avoid — you can use these to audit whatever you write.

So get creative, and have some fun. And, most importantly, use the word “Shipwreck” in all your email subject lines. (Note: This only applies if you’re emailing Chicagoans.)

Here’s Charlie’s contact info:

@Meyerson on Twitter


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Greg Mischio

Greg Mischio

Greg Mischio has been creating content for many moons. He is the Founder and CEO of Winbound, a sales and marketing agency that provides content and marketing services with a focus on manufacturing and industrial verticals.

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