11 lessons from five years of writing an email newsletter

I had a little bit of a special milestone this week. Creative Companion, which has been the backbone of my entire business for nearly five years now, crossed 10,000 total email subscribers.

Milestones like this are fairly arbitrary, but it still felt really good.

I remember how hard it was to get my first 100 subscribers, my first 500 subscribers, and my first 1,000 subscribers.

I only switched over to ConvertKit in August 2020, and more than 3 years in, I had only accrued 1,800 subscribers.

So the growth over the last couple of years has felt slower than anticipated. A lot of my business growth over the last five years has felt slower than anticipated. So I hope you don't fault me for taking a beat to celebrate.

But more importantly, it felt like a perfect time to compile a few of the major lessons I've learned when it comes to building an email newsletter to share right back with you.

1. Consistency comes first

Creating any content is an infinite game. It's a war of attrition. You need to get to a point where consistency is no longer a challenge.

As a byproduct of being consistent, you'll build a muscle of hitting deadlines without issue. You'll also naturally find your voice and the themes that are most interesting to you.

At that point, you can spend your time leveling up your game in terms of content and quality.

2. Things will get worse before they get better

When you first launch a newsletter, people close to you will sign up. Those people are excited for you and they want to support you!

But then you'll probably see people you care about unsubscribe. Your numbers will start to drop. Some of those people were never your ideal reader in the first place and they lose interest – that's OK!

Other people actually want to see you fail. It's brutal, but it's true.

There are a lot of people close to you who will subtlety and subconsciously stop rooting for you. They may even make conscious decisions to NOT be supportive. It's not really malicious, but people who AREN'T putting in the work to pursue their dreams may start to resent you for publicly pursuing yours.

3. Growth comes from specificity and novelty

If you want to grow quickly, be really specific. Be consistent not just in your publishing cadence but in the subject matter you talk about.

When you're incredibly specific, it's much easier to send a signal to a potential subscriber that what you're making is exactly for them. And in the beginning, that matters a whole lot.

This becomes even more powerful if that thing you're really specific about doesn't have other notable, well-known creators writing about it.

4. Subject lines matter a lot

You can write incredible emails. But if I don't open your email...I'll never see it. If I don't see it, I can't appreciate it. I won't build a bond with you and I certainly won't share your work.

Your subject line is the audition for the content you just put hours into writing – so take it seriously.

5. Aim to pass the regret test

When someone opens your email (nice work, subject line!) it doesn't have to be the BEST thing they've ever read. Remember, this is an infinite game you're playing – not every piece you write will be earth-shattering.

Instead, aim to pass what I call the regret test. It's really simple. I just opened your email – am I glad that I did that, or do I regret opening it?

As long as I don't regret opening your email, I'll open the next one. And that's another shot at playing the infinite game.

6. Soft skills matter in email too

There are a lot of incredible, technical writers. They have data, wonderful illustrations, interviews, they may even have footnotes!

You can have those things or you can focus on the more "soft" skills of writing too. You can focus on storytelling. You can focus on cadence or delivery. You can focus on showcasing your real human voice and personality!

It may attract a different type of reader than those technical newsletters, but there are certainly readers who are attracted to storytelling and humanity.

And if you can combine the two...even better!

7. Big ideas don't require big words

You may feel a lot of pressure to be profound and share your BIG ideas. That's fine, and you can totally do that! But big ideas don't require big words.

My mom is an English teacher and I was raised with a pretty stellar education in writing and grammar.

But as time has passed, I've chosen to ignore a lot of the thing we're taught in school about writing.

Most Americans read at below a 9th-grade reading level. That doesn't make anyone stupid – education and intellect go beyond reading ability.

But you don't need to paint your sentences with big, flowery words. You don't need to constantly flex your vocabulary (and risk losing your point in a word someone isn't familiar with). Write with smaller sentences. Use more line breaks. And feel free to start sentences with conjunctions!

It will make your writing easier to read and therefore easier to understand.

8. More stuff doesn't mean a better experience

If you're looking at other writers who are playing in a similar sandbox, you may be tempted to out-content them. In content writing, they sometimes call this the "skyscraper" model of writing articles – competing by writing MORE than your competitors.

Here's the thing – even if you write fantastic in-depth emails, if I'm expecting your email will take a while to read, I'll bookmark it to read later.

But...it's easy to forget to come back later.

People like to consume things that they can consume quickly and mark it as "done" in their brains. Writing long-form definitely appeals to some readers, but you need to make sure those are YOUR readers.

9. Create a front door and keep adding side doors

If you want more subscribers, you need to make it easy to subscribe. It should be really clear where I can subscribe to your writing – this is your front door.

And while that front door may be where 80% of your readers enter, you can still grow exponentially faster if you continue to create side doors too.

Side doors are other ways people can subscribe – they complement your front door.

Giving a presentation? Create a side door where people can receive your slides or some free resource afterward. Want to host a community challenge? Your landing page is a side door.

One of my biggest sources of growth this year has been from embedding email capture forms inside my articles. Those articles draw a lot of traffic every day from search engines, so adding a side door inside the articles has resulted in a ton of new subscribers.

There's really no limit to the number of side doors you can have – they have a specific purpose to capture attention that's already finding its way to you.

10. Lead magnets are almost prerequisite

I wrote about this a lot in my recent piece Lead magnets that actually work. Subscribing for "tips and tricks" isn't a compelling enough hook anymore – you need to offer something of higher value right off the bat.

11. You should use ConvertKit

Finally, I can't tell you how big of an impact moving from MailChimp to ConvertKit has been:

• It's more fun to write in
• The Automations are so, so powerful
• Tagging and Segmentation makes everything work better
• It's so easy to create landing pages and forms (side doors)
• The analytics behind ConvertKit help me understand what's working, where to double down, and what to improve.

ConvertKit offers a free plan. Even so, it's one of the biggest monthly/annual expenses in my business and I still feel like I'm getting a steal.

And if you want to go even deeper on this, consider enrolling in my Email Newsletter Workshop here. I'm going to be updating it soon, so if you enroll now you'll be able to watch the existing version and you'll get to join the recording of the new version for free.

Enjoy reading Creative Companion? If so, subscribe to my Sunday edition.

#92: Cathryn Lavery [Best is the Standard] – From Kickstarter to global 8-figure e-commerce business

Cathryn Lavery is the Founder & CEO of BestSelf. Since 2013 she's designed, launched and sold over $32 Million in consumer products.

Along the way, BestSelf Co. won Shopify’s Build a Business Competition in 2016 and the Build a BIGGER Business competition in 2017 – the only company to win both awards consecutively. We have been featured in the New York Times, Entrepreneur, MTV, Huffington Post, Forbes, Inc., and more. We’re funded solely through the investments made by thousands of customers who have used our products to change their lives.

In this episode, we talk about Cathryn’s first business as a 13-year old, her New York architecture job that put her back on the path to entrepreneurship, what’s changed for Kickstarter products and e-commerce businesses today, and why keeping Best as the Standard for her work has helped her find success in e-commerce.

🎧 Listen to the episode

About The Author

Hey, I'm Jay Clouse! I'm a full-time creator as a writer, podcaster, and community builder.

Most of my creative energy is directed towards my podcast, Creative Elements, and my newsletter, Creative Companion.

I've created a number of courses and workshops including my best-selling Podcast Like The Pros and my Freelancing School Course Bundle.

I previously led the Community Experience team for Pat Flynn and Smart Passive Income, designing their paid membership community and cohort-based course programs.

You can also connect with me on Twitter or Instagram.