A Guide to Becoming a Happy Newsletter Writer

The year is 2023. You have a newsletter, obviously. Now how do you make it successful? Wrong question.

This is not one of these posts on how to grow your audience and turn your newsletter into a subscription business. You’ll find good advice on that elsewhere. Rather, I will try to give you some ideas on how to develop a healthy and rewarding relationship with your newsletter, based on my experience from writing a newsletter for more than a decade.

This post is for you if…

• you want to start your own newsletter and not get frustrated after three months.
• you write a newsletter and it often feels like a burden.
• you’ve given up writing your newsletter and need some motivation to pick it up again.

1. Write it for yourself

Write a newsletter that provides value to you even if nobody was reading it. It’s a powerful means for building habits. When I started my newsletter more than 10 years ago, I did so because I wanted to spend more time actually reading the great things I discover on the web. And since I respond well to self-inflicted external pressure, I decided to start a newsletter with the best of the web, every week. It worked like a charm: I’ve built a solid habit of reading long articles, listening to podcasts, and exploring the web deeply. Turning my discoveries into a newsletter at the end of the week almost became an afterthought. What’s your intrinsic motivation?

2. Pick a frequency that works for you

People will tell you that in order to grow your audience, you should publish multiple times per week. Don’t listen to them. For one, there are plenty of counterexamples. And it’s not what we’re after here, anyway. Decide how the newsletter will fit in your life, and decide on a frequency that makes sense (you could also be a little smarter than me and not put the frequency in the newsletter’s name, so you can change it later if needed). Keep in mind: «Whenever I have the time and something to say» is a frequency, too.

3. Mute the unsubscribes

One of the more peculiar things about writing a newsletter is this: The first reaction to you sending it out is almost always someone unsubscribing. This isn’t about you. No matter how great your newsletter, there is always someone somewhere who has decided to cut down on their content diet and your newsletter happened to be a good opportunity to do so. Usually, your newsletter platform lets you know when someone unsubscribes — just opt out.

4. Take breaks when you need to

Writing a newsletter every week (or whatever frequency you’ve chosen for yourself) while life takes its twists and turns is tough. I’ve learned that there’s value in sticking to the habit even in weeks when I don’t feel like it. Then again, take breaks when you need to. In those ten years since starting the Weekly Filet, I’ve paused it twice for longer: when I started my first leadership role, and when I became a father. Both times, I restarted the newsletter when the itching was too strong — when I knew I’d get more joy than stress from doing it again. Returning to something you’ve missed feels wonderful.

5. Make sure you enjoy writing

It might sound obvious, but it’s worth mentioning: Only start (or continue) writing a newsletter if you actually enjoy writing. Or if you want to learn how to enjoy writing (see point 1). Unlike other contexts where we have to write things, with the newsletter it’s entirely up to you whether and what you want to write. Would be a shame if you didn’t enjoy it.

6. Don’t look at your subscriber list…

Just recently, when I needed to update a user’s profile, I happened to see that someone I greatly admire reads my newsletter. Sounds like a good thing, right? The problem I now have is that whenever I write, I can’t help but think of her reading it. That raises the bar to a level I can never achieve. Not helpful. When it comes to your subscriber list, ignorance is bliss.

7. …but also do look sometimes

Then again, seeing some familiar names and friendly faces in your subscriber list is helpful. It’s like speaking in front of a large audience and spotting a few people who you know root for you no matter what. Having those people in mind while writing your newsletter usually makes things a lot easier.

8. Beware of going paid

Driven by the rise of Substack, asking people to pay for your newsletter has gone mainstream. And that’s fine. Be aware, though, that going paid radically changes your relationship with your audience and your newsletter. The newsletter becomes an actual product, your readers become customers. As for yourself, you are no longer simply a writer, but have to market and sell your newsletter, too. I would recommend going paid only if you already have established your relationship to your newsletter, and have given serious thought to the opportunities and downsides.

9. Don’t compare yourself to others

Newsletters are everywhere. You’re probably reading lots of them each week. There is always someone who has the smarter takes, someone who writes more elegantly, and someone who gets more attention. It’s hard not to compare yourself to others (I’m guilty as charged). Try to be inspired, not awestruck. Try to learn from others, instead of envying them. Let them do their thing, and be happy with yours. (Chances are that they, too, are struggling. It always looks easy from the outside.)

10. Relax

If you follow the nine pieces of advice above, you should be a fairly relaxed newsletter writer already. You will still find yourself stressed now and then, overthinking every aspect of your newsletter. In this state of “Why the hell am I doing this?!”, try to focus on your intrinsic reason (see point 1) and forget about everything else. Even if you are ambitious about your newsletter, not every issue you send has to be the best you’ve ever written. Sometimes good enough is just that. (Bonus: Once you’ve settled for less, flow often returns. I’ve written some of my best newsletter issues when I struggled the most.)

My newsletter is called Weekly Filet. Every Friday, I send out a set of recommendations from all over the web, helping you make sense of the big issues of our time (with a healthy dose of serendipity and nerdiness). If you liked this article, I think you’ll like it, too.

If this was useful to you, share it with others. If I missed something important (I’m sure I have), please let me know.