My Boston Globe op-ed yesterday argued that blogging still matters. But it’s also got me wondering: Is the time ripe for newsletters again?

I wrote a personal newsletter for about ten years. It started out as an in-house mailer at Open Text where I was VP of Strategic Marketing in the mid-1990s. It came out every week or two and was titled DWOTIO: David Weinberger’s Open Text Inside Out (I think). News, views, humor, witty repartee with people who sent me email about it.

I’d coined the phrase “hyperlinked organization” there, and when I left I started a new newsletter called “Journal of the Hyperlinked Organization,” or JOHO. Hence the name of this blog. The phrase “hyperlinked organization” didn’t quite catch on (Deniro decided to make “Analyze This” instead), but I stuck with it and started sending out a free newsletter about every three weeks.

Each issue had one substantial essay, a couple more that were lighter and quicker, and witty repartee with people who sent me email about it. It also had a a humorous contest that no one ever entered, a “cool tool,” and a very brief write-up of an article about a company doing something interesting with the Web.

It took a lot of time, and not just to write it. It took me way longer to create HTML and text versions than you’d think; back then not all email readers supported HTML. Even just had formatting the HTML was a pain in the tuchus. (It’s way easier now, kids.)

But it was totally worth it. I had a direct connection to 7,000 people. They wrote in and I responded in the newsletter itself. It got me writing. When I wrote “In the future, everyone will be famous to 15 people,” that’s what I meant.

Then blogging happened.

For about ten years, I posted every day, often more than once. It took more and more of my energy. RSS let you subscribe to my blog. So what did my newsletter add? It faded away.

But now I’m thinking it might be time to start it up again.

Blogs are a pull medium, but not a lot of people pull on this blog. Newsletters are an opt-in push medium. I don’t know (and I don’t want to know — really, don’t tell me) how many people check my blog with any frequency, but I suspect it’s in the dozens. I love those people deeply, but that means that if I want to each a wider audience, I have to publish in the equivalent of online magazines. I do that and I’m truly glad for the opportunity. It’s a privilege. But that doesn’t establish the sort of intimacy that ritualized reading can.

It also means that my voice as an author works only for that one article, and the reader only hears me in that one voice. Turn the web page and the next author has to her establish her own presence. But a newsletter is a space that more fully expresses the author. JOHO was famously garish, ugly and amateurish. Welcome to me, people!

So, it’s tempting. I would still blog, of course. But: Can I come up with enough mid-range articles? Can I come up with a set of repeating pieces — like the old “Cool tools” — that will be interesting enough but won’t paint me into a corner? Would anyone read it? Would it be worth the commitment?

I don’t know.

But I’m not the only blogger in this situation. With mainstream web magazines providing a way to reach a lot of people with longer-form articles, blogs working for shorter and more informal pieces (or for anything you want), Facebook for quick personal posts, and everything else for everything else, the ecosystem might be ready for the next round of personal newsletters. Maybe.

Categories: misc dw