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How to Write Better Subject Lines

So… since work I work in CRM as a copywriter, the one thing that I’ve become absolutely obsessed with are subject lines.

I know, I know, subject lines– who cares, am I right? Well I do, that’s why I’ve got a backlog of some 60k+ emails in my inbox, because I’ve subscribed to I DON’T KNOW HOW MANY retailers, service providers, etc. because I’m truly interested in seeing how other businesses write this copy.

And it feels like it’s a last thought for some. Just take a look at this… come here and take a look at this:

It’s the new millenium, some 91% of customers EXPECT free shipping, according to a survey by Material Handling & Logistics. In fact, according to the same survey, they prefer free shipping over fast shipping.

So – this doesn’t really blow anyone’s skirt up.

I don’t even know what this means. Last day to what? Be on fire?

OK so it’s been roughly 3 months since I searched for Hammocks on Wayfair, and on at least a weekly cadence, I get this retargeting email AND a pushy push notification reminding me that they do indeed have HAMMOCKS in every style + size.

As an email marketing copywriter, these are all things that I’m hyper-aware of 1) because that’s my job and 2) because, again, I got like 60K retail emails in my inbox right now. I’m a little obsessed.

But how can you, oh small business-owner, or copywriter who wants to write better subject lines, actually write better subject lines? I’m glad you asked.

Here are some tips:

If You Use Emojis – Do So Sensibly

I’ve gotten some pretty interesting emails with obnoxious use of emojis. The worst offender was just a subject line with 32 red exclamation points. That’s it. Imagine this guy ❗ 32 times in a subject line. Yikes. How they didn’t end up in my SPAM folder is a question for another day. 

Know Your Content

When used wisely, emojis can increase opens and read rates. Use an emoji that actually relates to what your email is about. If you’re running a promo on clothes or shoes – use a dress, pants or shoes emoji. If you’re a gym that’s promoting new crossfit classes – hey flexed bicep 💪. Write your subject line with the content of your email in mind.

Testing! Testing! 1, 2, 3

I’m pretty sure it was Jack Donaghy who said in Glengarry Glen Ross to “Always Be Closing.”


I love 30 Rock, OK?

Well, in email, you should “Always Be Testing” Customers are ever-evolving to how they relate to content and testing is one way to gauge their behaviors. With subject lines, you can test Emojis & Emoji Placement, Savings vs. Value Message, Playful vs. Straightforward, Multiple Emojis vs. No Emojis, Long Vs. Short Subject Lines… pretty much the list goes on. Always be taking what you learn from those tests to inform future subject line copy and you’ll be on your way to writing great subject lines.

Need some testing ideas? Check out Campaign Monitor’s Ultimate Email Subject Line Testing Checklist.  Hubspot’s also got a great post on Subject Line Testing Tools – I think my favorite is probably CoSchedule since it really breaks down a subject line by emotion, length, word use, etc. Check it out!


In summary, I love subject lines and I’m always trying to write better subject lines or at least write subject lines that get more opens than I did last year. These are real tips that I really use on the job, and subject line copy is just soooo undervalued and over-emojied sometimes. But I hope you found this helpful and will take these words to your subject line bank and get more opens and clicks.

Oh and I just checked… I actually have closer to 69K emails in my inbox.

That’s my bad, guys.


The Perennial Short Shrift

“If you’re a freelance writer and aren’t used to being ignored, neglected, and generally given short shrift, you must not have been in the business very long.”

– Poppy Brite –

In my nine years of working for myself as a writer, this is one thing I know; it’s that the one thing you HAVE to get used to being told no. Actually, wait, no. To wit, a writer is lucky if they receive a, “no.”

I actually like receiving the “Thanks, but no thanks,” email from an editor, because it’s life-affirming proof that they DO read your emails. And what’s more affirming is that something about your email caught their eye just long enough to disinterest them. Oh and when an editor tells you WHY your idea sucks (that’s hyperbole) or that you should pitch some other publication… manna from heaven. It’s the no’s that shape you and the criticism that helps you grow.

That said, get used to being ignored. I’m pretty sure the Internet is a black hole.

Adventures in Freelancing

What is this? Where am I?

Hi. I’m Lindsey. This is my blog on living the accidental, kind of awesome, though sometimes sucky, freelance life. I started this blog about 6 months ago because I thought it would be a good idea to journal what it’s like to be a freelance writer. In neither high school, nor in college, no one tells you what it’s like to work as a writer.

During college — I have briefly flirted with a higher education for nearly a decade now — I grew up with dreams of moving to NYC and becoming a high-fashion, ballsy, mean, childless editrix at some fancy magazine. I was going to be awesome.

However, that didn’t happen.

Dreams were dashed and I needed a real job because you can’t pay the rent with dreams and aspirations.

So I did what most aspiring writers do, I took random jobs in restaurants, until I eventually landed my first real job as an accountant.

Accounting? Yes, that. A bean counting, paper-pushing, coffee-drinking, time card-punching accountant and I hated every last minute of it. I have worked a million jobs in restaurants and hotels and quite frankly, have never experienced anything so soul-crunching as working in room the size of a tuna can, counting money and recording that counted money.

Plus, I was bad at math. I had no idea why they even hired me. I was there for a little over two years before I gave myself the heave-ho. It turns out, I would rather eat beans out of a can and at least attempt to get my dream career back on track, than working a low-rent job just because I had good health insurance.

Here I am, I don’t even KNOW how many years later, finally writing this blog’s first real entry. Along the way I’ve managed to forge something resembling an actual career as a writer, something that amazes the most random people. Yes, I do get to write things…it’s amazing! And even though I’m not where I’d like to be in my career, I am on the way there. It’s not what I set out to do, but I’m having fun for the most part. I realized along the way that while I no longer aspire to be Anna Wintour — she always looks hungry and mad — or Stephanie Meyer — as if! — I wouldn’t mind AJ Jacob’s career. It’s pretty sweet.

What you’ll find here: trials, tribulations, hilarious stories of crappy clients, fun projects, words of aspiration and whatever else I feel like cause it’s my blog and I’ll whine when I want to.