The Downtime Guide To: Writing A Newsletter

Larry Fitzmaurice

Everyone has a newsletter these days. Here's how to stand out from the pack.

There’s plenty of reasons why you might want to start a newsletter. Perhaps you’re an established writer looking to strike it out on your own apart from your media day job. Maybe you’re just starting out and looking for a way to hone your chops while also building a readership. You could be extremely passionate about a topic that you’ve always wanted your own space to wax endlessly on—or, maybe you’ve just felt cooped up in your home these days and want another way to reach out to anyone else who’s feeling similar.

Either way, there’s no better time to launch your own newsletter. The whole world is, figuratively, your captive audience—and even if you reach just a few people, the interpersonal connections it provides can be rewarding. But there are some things you should keep in mind before kicking off your own personal publishing outlet, so let’s run them down.

What are you going to write about?

This one sounds obvious, but more often than not it’s the obvious things that are the most important. So: what’s your angle?

Is it something more general like movies, sports, or politics? Or are you looking to zero in on something specific, like birding in the Pacific Northwest or the history of a particular skateboarding trick? There’s pluses and minuses to either approach. A broad range of topical coverage means you’ll have the ability to pull readers in from various fields of interest—but, if you don’t already have a considerable profile as a writer, you may find yourself competing for oxygen (more specifically, readership) from others with a greater pull audience-wise. Choosing a more specific focus means that you’ll be able to stand out in what is increasingly a crowded field—but, it also means you might be limiting the size of your readership off the bat. Either way, it’s important to be confident about what your scope is straight off the bat, especially to communicate to your readers what to expect as you continue to publish installments.

What are you going to call it?

A name for your newsletter: it’s important! And it’s probably going to be one of the hardest parts of the process leading up to actually, y’know, launching your newsletter. You might be compelled to be witty, but remember—it’s painfully obvious when someone is trying to be too witty. Maybe you’re going to reference some pop cultural artifact within your title. That’s fine! Just make sure you aren’t violating copyrights, otherwise a cease-and-desist down the road can hamper your attempt to solidify a branding for your newsletter.

Maybe your name is James or Molly and you’d like to call it “James’ Newsletter” or “Molly’s Corner.” Hey, if you’re going the super-simple route, I’m not going to judge. The point is, coming up with a name is important if only because, in the act of people potentially recommending your newsletter to others, they’re gonna need to tell them what it’s called. Don’t necessarily break your back thinking of a name, but give it some serious thought, too.

How often are you going to send it out?

Look—you don’t have to have a plan regarding the frequency of your newsletter. It really depends on how serious you’re going to be about posting. You can get away from updating it whenever you want and no one will judge you. It can essentially function as a nice, occasional surprise in someone’s inbox. However: it might be helpful to have somewhat of a plan starting out. For one, establishing a regularity with your readership could give them something to look forward to, and it helps build anticipation for your next installment.

Also, making your newsletter part of your regular routine might just install a better work ethic regarding writing (especially if your reasons for starting a newsletter involve improving or sharpening your own writing skills). Establishing a posting-schedule strategy is essentially another way to keep organized, as well as a way to make sure you don’t feel overwhelmed as you navigate the waters of self-publishing.

Are You Gonna Make People Pay For It?

I know, I know—money can be a touchy subject, especially (gestures in the air) in these times. But you should consider the value of what you’ll be providing, as well as what you feel comfortable asking people for. Perhaps you want to go strictly paid subscription-based with no free posts. (I wouldn’t recommend this, at least starting out.) Maybe you’d like to do all free posts with an optional donation and/or subscription option. Or you’re thinking of striking a balance between those two opposing poles, offering some subscriber-only posts and some free posts—the former to create value for those who are generous enough to pay for your work, the latter to entice new subscribers and expand your base. I would honestly recommend that route, but we’re also so early on in the age of newsletters-as-media that it’s best to do what you’re most comfortable with.

Where Are You Gonna Publish This Thing, Anyway?

As of right now, the most popular option for self-publishing a newsletter is Substack, a blog-like platform with limited customization but an easy-to-use CMS interface and generally streamlined operations. Perhaps you’re gonna just go with Substack. That’s ok! But if you’re interested in other, slightly more arcane options—creating a listserv, using a mass-mailing service like MailChimp, etc—the tools are there for you to get creative.

As far as paid newsletters are concerned, though, Substack is at this point the easiest platform to use when it comes to monetizing. Will that change at some point? Probably. What doesn’t change these days?

Are You Stressing Out Too Much About Starting a Newsletter?


Look, the most freeing thing about publishing a newsletter on your own is that it’s your newsletter. You can do whatever you want with it, whenever you want. The overhead is minimal if not entirely nonexistent, and if at any point you feel like you want the scope of the newsletter to change—or, if you just want to change anything about your approach at all—it’s totally okay to do so. There’s no editors over your shoulder (although, if you have a peer network willing to look at your work every now and again, I’d recommend it—no one is too good for having a decent editor on their side). There’s no investors to answer to beyond your loyal paid subscribers. (And if you ever lose paid subscribers—and you will, for whatever reason—don’t panic, and don’t take it as a personal affront. Everyone has reasons not to pay for things these days.) Above all else, have fun with this. It’s yours, and the more you enjoy that fact, the better your work will read for yourself and others.

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