Every time I sign up for a new newsletter, I cross my fingers and hope. And almost invariably, I am disappointed. It’s very hard, apparently, to get a newsletter right, and really, really easy to screw it up.

Now that I’m in the throes of creating my own newsletter, I’ve started looking at others’ with an even closer eye. Here’s a little of what I’ve learned.

1. Content is king

I’m a designer. I like things to look nice. Of my three favorite newsletters, one is text-only and one is, um, ugly. I read that sucker every Friday morning, stem to stern. And for the record, that third newsletter? A miraculous combination of nice looks and great content.

2. Leave me wanting more

Of course, there is almost no such thing as too long if your content is good enough. But why kill yourself? You’ve got 51 more weeks to fill, cowboy. Besides, the point of the newsletter, as I understand it, is to get someone interested in your business. I would think the two greatest ways to do that are to tell me incredibly useful information, thereby establishing yourself as an expert, and to leave me wanting more of your expertise.

3. Watch the ads

Hey—it’s your dime and your time. I can understand an ad or promo here or there. Just be careful. No one’s content is that good.

4. Be as regular as taxes.

Those "when I feel like it" newsletters? Those are articles. Unless you are one of maybe 25 people whose words I hang on, I’m not interested in your articles. Really—I’m not.

5. Regular means once per week, per two weeks and if you’re amazing, per month.

I mean, go ahead and send me that once per month email. But know that there are some people sending me an emailed newsletter with great content every week. Which means maybe consider #1 & #2 and go back to the drawing board.

6. Think long and hard before using that email I gave you to send me something else.

I’ll give you one, maybe two shots. Then you’re outta there.

7. Keep the self-congratulations for friends and family.

I almost never care if you’ve won something. Unless it directly affects me, in which case, knock yourself out.

8. An HTML email with links back to your site instead of embedded content is not a newsletter.

It is a pain in the ass standing in the way of me and information. Don’t do it.

9. Keep it within your purview, but useful to me.

One of my new favorite newsletters is Mark Silver’s text-only Business Heart. Silver’s area of expertise is "heart-centered business practice"—in other words, how to do business without feeling like a tool. He’s focused and passionate about what he does,  consistent, respectful, gives openly and doesn’t push. Guess who I’m going to refer someone to first when they’re looking for a coach like him?

10. When in doubt, offer tips.

Rebecca Morgan and Ken Braly’s SpeakerNet News gets read first, every Friday, even before I click on my Salon links. Even if you’re not a speaker, you’ll learn plenty from the myriad excellent tips on self-promotion, marketing, travel, organizing, systems, etc. In fact, if someone has a newsletter for me that is as good as SNN and has only organizational stuff, I will pay you five American dollars. (I must subscribe to it for at least one month before you receive your prize.)

11. If you’re going to imitate someone, imitate someone good.

Most newsletters look sadly alike. I guess this is partly a function of fear, and perhaps partly owing to the sameness that plug-and-play eNewsletter template creators offer. One of the few exceptions I’ve seen is the Very Short List, a one-(cool)-item per day offering written by some really smart people and designed by some really good designer. It’s a good use of code and design: i.e., to make things more, not less legible. And of course, killer content.

12. Don’t forget outbound links.

This last idea came straight from a newsletter! It’s kind of a corollary of Rule #1, but enough of a good point
to bear mentioning on its own. I like goodies! All people like goodies!
Give away goodies! Lots of other good stuff in this article, although
the newsletter itself breaks Rule #8, so it doesn’t make the hit
parade. via Nick Usborne in "Four Ways the Best Newsletters Are Like
Blogs," from the MarketingProfs.com newsletter (link)

Note: this is a slightly edited version of a post I made on my own blog, communicatrix, last month. Ilise thought it was worth getting in front of a larger audience, and we both figured it would be great to start a dialogue about what you all think of newsletters—good, bad, indifferent.

So…what does make you keep from hitting the "unsubscribe" button? What would you like to see more of in newsletters? Less of? And of course, what have you learned from sending out your own newsletter?