15 Lessons From 30+ Years in Newsletters

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This story is excerpted from CJ Chilvers’ new book, “Principles for Newsletters,” available for purchase on Gumroad.

My first newsletter was about ninjas. It was 1987. I was 12.

Since that first ninja newsletter, I’ve been obsessed with the format, no matter how it was delivered.

A good newsletter forces clarity, brevity, and utility in a cluttered, information-dense world.

I transitioned to digital newsletters about small business and creativity in the 1990s — first on floppy discs I sent through the mail, then by email when that became possible.

I’ve created tiny newsletters for my own projects and giant newsletters for some of the biggest corporations on the planet. Through multiple boom and bust cycles, no matter the size of the newsletter, some truths are constant.

These are some of the lessons I’ve written down for myself along the way, often after a failure. I hope you can put some of my mistakes to good use for your subscribers.

1.) You need a newsletter.

You are a publisher now, whether you asked to be or not. In some form, your information, your content, and your story are out there somewhere. 

Take ownership. 

Publish. 

If you aren’t telling the story of your work, business, or life, someone else will. This is already happening in everything from social media posts to search results.

You may already publish or want to publish something for yourself or as a business — for fun or for profit. Publish a newsletter. It still returns, by far, the most for your investment.

2.) All newsletters are personal.

Forget about the differences between personal and business newsletters.

Whether expressed or not, all email newsletters are — at their core — personal newsletters. Email is an intimate, one-to-one medium where the biggest companies on the planet compete for attention with notes from Grandma. Almost every challenge a newsletter publisher faces is based on the denial of this basic truth.

Trust is the currency of this medium. People trust people more than companies, organizations, or governments.

Trust resists automation. As trust in auto-generated, ad-inundated, broadcast newsletters erodes, real human names and faces will emerge as the most trusted “brands” in their area of interest or industry.

No one likes being thought of as a “brand,” but there is a better word for it. Your brand is just your reputation.

Companies will face declining returns on their marketing because of eroding trust and then have to hire or acquire trust at great expense.

You can start now for free.

That’s the power of your newsletter. It’s the hub for everything else you build. It’s where you establish trust. It’s where you create and maintain your reputation.

Start any kind of newsletter you want, but continue building relationships and trust in your name.

3.) There is no competition for your personal voice.

It’s easy to replicate a business model. It’s really hard to replicate a personality.

Chances are, whatever your newsletter is about, there are many others sharing the same ideas and links. The only thing that separates them is voice.

Your voice is unique. Make sure it’s reflected in what you publish.

4.) No one cares.

You have to give them reasons to care. 

Earn five seconds of their attention. 

Then, earn the next five. 

Repeat.

5.) Curate.

There are way too many creators and not enough editors. The current crush of mediocre content will only increase. We need picky people with fine-tuned bullshit detectors to comb through it all and surface the good stuff.

The curation newsletter format, linking to the best of the best with a little personal commentary, works because your readers are looking for answers for multiple microproblems within a topic. It’s never just one. 

Think of it as a lottery. You can try to get attention from a headline and have one chance to connect with your readers. Or you can offer several interesting headlines from multiple sources, including yourself, increasing your odds that something will speak to your reader enough to be considered useful. 

Sharing useful information is powerful. Finding the best content fills your personal network with the best creators. It does the same for readers. There’s nothing more valuable than being the hub of all those connections.

Curate your archives as strategically as your newsletter. Your archives are the searchable, text-based representation of the network hub you’ve built. Readers don’t search chronological archives on websites like they did decades ago. Repurpose that archive to create guides, books, podcasts, and videos — whatever forms of media your audience prefers to consume.

Your archive is the foundation for your future products and services. Keep it useful. Keep it curated.

But understand that curation is hard.

A useful, curation-based newsletter is more difficult to publish than any other kind of newsletter.

• It takes longer.
• It requires a defined process over time to be consistent. 
• It requires deep knowledge of the subject matter. 
• It requires the interest, time, and effort to seek out the highest-quality links. 
• It requires enough knowledge of a community to know which links are the most valuable to the reader. 

Curation favors individual humans being useful to other individual humans. It’s the simplest form of content in concept. It’s the hardest to execute in practice. It’s an enormous opportunity for creators who want to stand out.

6.) Be brave. Be brief.

Brevity is considerate, difficult, and valuable.

Concise writing takes more work, but it’s more likely to be read.

Most books should be a blog post. Most blog posts should be social media posts. Most social media posts shouldn’t be.

Conquer email obesity. Deliver maximum value per pixel.

7.) When stuck, apply another constraint.

Constraints boost creativity. 

Can’t write an essay? Write a paragraph. Can’t write a paragraph? Write a sentence. Eventually, you will find a constraint that makes daily creation possible.

The trick for consistent newsletter publishing is finding useful constraints for both you and your subscribers.

What is useful to your audience?

• Getting to the point
• Finding obscure ideas, people, and resources for solving specific challenges
• Finding entertaining ideas, people, and resources
• Providing more value than you ask for in return
• Having a consistent publishing schedule

What is not useful to your audience?

• Over-designing
• Over-formatting

What is useful for you?

• Limiting words and topics
• Limiting when or how your work is published
• Using process-based templates and automation
• Being imperfect
• Having a consistent publishing schedule

What is not useful for you?

• Using templates and automation that detract from your publishing voice
• Publishing and marketing based on trends
• Being acceptable to everyone

8.) Don’t automate relationships.

All parts of the newsletter process can be automated, but not all should be. 

There’s an uncanny valley that too many newsletters enter with complex automation schemes. The more complex the scheme, the more you begin to rely on apps to tell you who your readers are and what your content should be.

It’s best to keep your process simple for as long as possible.

Properly placed automations should occur to you over time and should never come at a cost to the relationship you have with your readers or the quality of the content.

9.) Only one person is opening this email.

You are not a broadcaster. Crowds are not gathering around a single screen to read your email. 

Write to one reader.

10.) Recognize what delights you about other newsletters.

It’s not necessarily what engages you. That’s too easy. Machines can do that. 

Engagement is good for a few sentences. Delight builds anticipation for the next issue. 

You’re probably not producing enough delight.

11.) Focus on your “Sent-From” line.

Subject lines don’t matter anywhere near as much as your sent-from line.

Small changes to a subject line can produce small improvements. Small changes to a sent-from line can make or break a newsletter entirely.

The sent-from line is the first thing a reader reads. It’s big and bold above the subject line. The reader often decides the value of the email at the sent-from line before they get to the subject line — if they get to the subject line.

Trust is the only thing that improves your sent-from line.

12.) Monetization is a byproduct.

If you build an audience to serve that audience, monetization will present itself. You don’t need to chase it. You don’t even need to accept it if you don’t want the added responsibility.

13.) Give more away for free.

Nothing is more valuable than the relationships you’re building. Projects come and go, succeed and fail. The audience should remain. What attracts and keeps them is what you’re giving away. 

You’re probably not giving enough away.

14.) Inspiration is scheduled.

It’s also called work.

The common denominator of all work isn’t projects, attention, or energy. It’s time. 

Humans are horrible at estimating time. Schedules tame your illusions about time.

Your schedule is there to keep you consistent and sane — while creating the proper amount of space to work. Your schedule is the foundation of your process.

This means scheduling time for leisure, too. All work and no play makes for a boring newsletter. 

Email publishers don’t want to admit they’re in the entertainment business, but they are. What makes you entertaining? What is entertaining to your audience? 

How can you make this all a little more fun and interesting for everyone?

15.) Celebrate and share the wins of others.

Be the cheerleader for your topic.

Your competition isn’t other creators. Your competition is:

• Short attention spans
• Unlimited life distractions
• Limited awareness that you exist

A win for creators in your community is a win for your community. Promote those wins. Build relationships within the community.

My longest-term readers and customers are fellow creators. That wouldn’t be true if I had treated them like competitors.

CJ Chilvers’ new book, “Principles for Newsletters,” features 49 lessons from more than three decades of working with newsletters. You can buy it now on Gumroad.

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