35 Lessons from 35 Years of Newsletter Publishing

2 Jan 2022 — 4 min read

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

Since then, I’ve been obsessed. I’ve created small newsletters for my own projects, and big newsletters for corporations. What ties them all together? Probably hundreds of things, but I’m lazy, so let’s start with 35.

I won’t lie — most of these lessons here were learned by failure. That’s OK. My mistakes could be your head start.

Email lasts. You will have a medium that best speaks to your style (maybe audio or video is what keeps you excited), but email is as universal as we’ve gotten online as a species, so far. It’s still the king.
There is no competition for your personal voice.
Build relationships. That’s what it’s all about. Anyone trying anything else is lying to themselves or their readers. All you need is one relationship to change or save your project, career, or life. Why not establish more? This is also what separates the wealthy from the successful.
Be human. People recognize spam. People recognize a sales pitch. People also recognize honest, direct communication. This is where newsletters excel. Be real. Be vulnerable.
The best metric is replies.
Perfection sucks and it’s boring.
No one cares. You have to give them reasons to care. Earn five seconds of their attention. Then, earn the next five. Repeat.
New idea? Just start. You can’t establish relationships if you’re not out there. Whatever it takes, get your idea out there now. Course correct, if and when needed. Every failure is possible entertainment for your audience. So, just ship.
Curation matters. There’s way too many creators and not enough editors. This scarcity creates value.
There’s bravery in brevity. Small is considerate, difficult, and valuable. Most books should be a blog post. Most blog posts should be a tweet. Most tweets shouldn’t be.
Be consistent. People are creatures of habit. That’s why consistency works. Become a part of their routine.
Your newsletter is the byproduct of your process. Focus on improving your process and everything else works itself out. This is where you learn how to stay consistent and avoid burn out.
Deliver value, not word counts. Solve someone else’s problem — the bigger the better. It’s nice if it solves your problem too.
Don’t be an asshole. Make it easy to unsubscribe. Don’t get bogged down in tracking clicks. Respond. People are not “opens.” People are not “clicks.”
Only one person is opening this email. You are not a broadcaster. No one is crowded around a single screen reading your email. You are writing to one, individual reader.
Give a shit. It’s shocking how many don’t.
Discovery is recovery. You’ve covered topics a thousand times without realizing they intersect in new and interesting ways. Re-read your stuff and you’ll find something new every time.
No size fits all. No matter what you do, you won’t please your entire audience. That’s good. Build trust by being honest and you’re bound to get hate. Remember: the opposite of love isn’t hate, it’s indifference.
Keep track of what delights you about other newsletters — not what engages you (that’s too easy — A.I. can do that). Engagement is good for a few sentences. Delight builds anticipation for the next issue. You’re probably not producing enough delight. You probably should be.
Subject lines don’t matter anywhere near as much as your From line. Trust is the only thing that improves your From line.
Add your newsletter link to all the things. Make it the center of your online universe, because it’s where relationships are built. If you build a newsletter of value, it’s your duty to expose it to as many readers as possible.
Put your best link forward. Value must be made apparent quickly. What gets linked to first, gets clicked on the most — make it valuable enough for the reader to want to return to your newsletter.
Cut ruthlessly. In projects and processes: delete first, organize and automate later. Properly-placed automations should occur to you over time and should never come at the cost to the relationship you have with your readers or the quality of the content.
Your brain doesn’t know the difference between announcing something and shipping it. Announcements are easy, tempting content in newsletters. If you post an announcement, add something to make you accountable to your audience to actually ship (like pre-sales).
Meet your subscribers. When you meet readers in person, you get a better understanding of how what you do fits in their world. It shapes the way you publish, as well as what you publish.
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.
Pick a day, any day. Publish in a manner and at a time that best fits your habits or strategy, not when stats on the general public tells you to. Your audience is not like anyone else’s. You have more control over your publishing schedule than anyone will admit.
Ask for testimonials. New readers want to know why they should care about your newsletter. Give them real reasons from real readers.
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.
Inspiration is scheduled. It’s also called work. The common denominator of our tasks, projects, and entire lives is time. Your schedule is there to keep you consistent and sane. It’s the foundation of your process.
Schedule play too. All work and no play makes for a boring newsletter. “Leisure is the basis of culture.” How cultured and interesting can you be if you’re not scheduling time for leisure? Creators 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 for everyone?
Create daily. You don’t have to publish daily, but creation is the habit that makes everything else possible.
When stuck, apply another constraint.
Celebrate and share the wins of others — always. Be the cheerleader for your topic.
Unlearn. Everything changes. It’s the only constant. Be ready to unlearn in an instant when presented with new information.